The Chicago Guide

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 on 2022.02.03
Multiple locations
95 Places
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Chicago is easy to love. First, there’s the famous Midwestern charm, which can’t be overstated and seems genetically wired in its inhabitants. People are just really nice here. Then, of course, there are world class museums, parks, parks, parks everywhere you look, and so many great restaurants we’ve barely made a dent in our checklist. And every year, it just gets better. Formerly off-the-beaten path neighborhoods, like Logan Square and Bucktown, are now front-and-center when it comes to Chicago’s new crop of hip watering holes, while old school haunts, like The Peninsula (one of GP’s favorites), are getting fresh, modern makeovers. As much as we love sharing everything new, though, we’re also rediscovering cultural institutions, shops, and restaurants that deserve newfound attention. It’s this uniquely Chicago mix, after all, that makes this city so endlessly exciting.

Annette's Italian Ice

Ice cream shop · Sheffield Neighbors

"This no-frills, walk-up window shop in Lincoln Park (with a small patio) is known in part for its wide range of Italian ice flavors (from lychee to pink lemonade and chocolate). But if Italian ice isn't your thing, the smoothies or ice cream concoctions here will do just fine."

"Over a century ago, this Michigan Avenue landmark served as home base of the Chicago Athletic Association. The building had been vacant since 1997, so it was a pretty big deal when design firm Roman and Williams stepped in to re-imagine the massive building as a slick 241-room hotel. Sport is still a prominent theme here, as evidenced by a tricked out game room and walls of museum quality athletic memorabilia. And while the stained glass windows, grand ballroom, and general clubbiness were left intact, the brass lighting fixtures and leather furniture (both in-room and throughout the hotel) are welcome additions. There's also the sexy rooftop restaurant, Cindy's, a Shake Shack, and three more places to eat and drink. Incidentally, the cozy library at Cindy's is an excellent place to host a private event—it doesn't feel at all like a corporate hotel space, and the views of Lake Michigan are jaw-dropping."

Cowshed Spa Chicago

Spa · West Town

"This British import, located inside the Soho House in Chicago's buzzy West Loop, offers extraordinarily comfy treatment chairs and farmhouse vibes. It's particularly popular for its indulgent manis and pedis (60 and 75 minutes, respectively): Each of the chairs features its own TV and freshly brewed tea served in a teapot is available upon request. There are only five treatment rooms, but they'll do everything from facials (some with SkinCeuticals products) to body wraps, scrubs, and deep tissue massages. "

The Peninsula Spa

Spa · Magnificent Mile

"The spa is high up on the 19th and 20th floors of the hotel, and the treatments are beyond-pampering and impressively corrective. The Cryo 3R Facial uses chilled air to regenerate skin and support collagen (you look remarkably glowy immediately after), while the European Deep Cleansing Facial involves a revitalizing massage, thorough pore detoxification, and layer upon layer of nourishing serums and creams. There's a eucalyptus steam room, as well as a relaxation room where you can curl up next to a fireplace. The facials can absolutely stand alone, but if you're splurging, consider one of the famous half- or full-day spa journeys."

Punch Bowl Social Chicago

American restaurant · West Town

"A 1950’s style diner, a bowling alley, karaoke rooms, and an arcade room are all under one roof at Punch Bowl Social, a 30,000 square-foot adult playground in the West Loop. It’s a little kitschy but fun when you’re in the mood to let loose. Even if a round of bowling or belting out a few karaoke tunes isn’t in the cards, it’s worth a visit for the food alone, which leans towards comforting staples, like buttermilk-brined southern fried chicken and big burgers made with grass-fed, hormone-free beef. Otherwise, healthier, lighter fare is available too, including a superfood grain bowl, loaded with quinoa, kale, radishes, sprouts, roasted carrots, pickled chiles, and shiitake mushrooms. "

Gaslight Coffee Roasters

Coffee shop · Logan Square

"It may appear to be one of those hipster, brick coffee houses that are ubiquitous these days, but this Logan Square roaster also happens to serve an excellent breakfast and lunch, too. Locals swear by the duck egg benedict and house made pickles, and the tartines (ricotta with pear, prosciutto and olive oil; salmon with goat cheese, capers and chives) make for great snacks in between exploring the area’s vintage and specialty stores. Pro tip: Buy a bag of Gaslight’s beans to bring home, and you’ll get your coffee order for free. "

Oromo Cafe

Cafe · Lincoln Square

"Tired of almond milk? This is your place. This colorful little place gives the health-obsessed cafés of L.A. a serious run for their money when it comes to alternative creamers. Pistachios, pecans, hazelnuts, and coconuts are all soaked, pressed, blitzed, and strained for the perfect velvety, dairy-free latte. These nutty elixirs are spiked with all manner of adaptogens and superfoods (ashwagandha, moringa, maca, camu camu) for a supercharged, super healthy pick-me-up. The coconut Cubano—hot espresso poured over a teaspoon of coconut sugar—is the perfect marriage of syrupy sweetness and bitter heat. "

Soho House Chicago

Social club · West Town

"Scoring a membership here is like hitting the Soho House jackpot: There’s a rooftop pool, a killer house restaurant (and a separate white-tablecloth option), Cowshed spa, tricked-out gym with boxing ring, and a 40-room hotel. Including the two public restaurants on the ground floor (Chicken Shop and Pizza East), this is the largest space on the roster. And while it’s been a long time coming (nine years since Nick Jones first set his sights on Chi town), this outpost looks and feels like it fits right in with its cool West Loop surroundings. "

The Langham, Chicago

Hotel · Near North Side

"Only a few years old, this 300+ room hotel takes up the first 13 floors of the Mies van der Rohe-designed IBM building (it’s actually the architect’s final work) but feels more like a boutique operation rather than a corporate-y behemoth. That said, it’s well equipped to host both business and leisure-minded travelers: spacious rooms, a choice of on-site restaurants, and a killer spa. It also offers all the thoughtful extras one might expect from a Langham, including afternoon tea service and a mini fleet of the signature pink taxis."

Waldorf Astoria Chicago

Hotel · Gold Coast

"The Waldorf’s massive, elegantly appointed guestrooms—a good portion of which have working fireplaces—are just one of the many reasons why we chose it as our home away from home during the Chicago goop pop (it actually used to be the Elysian, another goop fave). Here, a heated porte-cochère (a godsend during those brutal Midwestern winters) gives you the sense that comfort is taken very seriously before you even step through the doors. Balsan, the on-site bistro, has a solid selection of classic American fare (burgers, salads, and super fresh oysters), so leaving the grounds for a great market-driven meal isn’t a necessity."

The Peninsula Chicago

Hotel · Magnificent Mile

"We don’t say this much—or ever—but: The Peninsula is maybe our favorite urban hotel in the entire country. It was recently renovated, which, in this case, means new custom artwork in the guest rooms (including silk floral wall prints), tablet technology for controlling everything (lights, curtains, room service) by touchpad, and a new cocktail lounge, Z Bar, perched high above Michigan Avenue, where drinks are made tableside on a roving cart. Sipping an Old Fashioned here while soaking in the rooftop views before heading to your room and falling asleep on Pretesi linens in one of the Peninsula’s supremely comfortable beds…this is the perfect Chicago evening. "

Royal Sonesta Chicago River North

Hotel · Near North Side

"Located in the hub of the art and design district, the Palomar is a modern, pet-friendly, eco-friendly, organic-oriented hotel that caters to active city visitors. The hotel organizes fun group exercise classes that include guided runs along Lake Michigan and ballet barre workouts on the hotel’s sundeck. Other novel perks are the in-room massages and yoga sessions. And, if you travel with your pets, you’ll be pleased with all the amenities that they’ll enjoy. Sable, one of the best bars around, is just down the stairs."

Freehand Chicago

Hotel · Near North Side

"The second Freehand outpost (the first is in Miami) refers to itself as a hotel-slash-hostel, meaning they've made their beautifully appointed shared and private rooms exceptionally tourist and wallet-friendly. Designed by goop favorites Roman and Williams, it's all understated, eclectic comfort through and through: Public areas are set up like living rooms with a cafe and bar right on property—that's all in addition to a 24/7 communal kitchen. "

Girl & The Goat

New American restaurant · West Town

"We love Stephanie Izard's Girl & The Goat because craft is the key to every single one of the dishes. The food is separated into three categories—meat, fish, and vegetables—with plenty of crossover in between. Combinations are unexpected and bold flavors abound, all with a feminine, comfortable touch. Don’t miss the selection of house-made breads served at the beginning of each meal, and if you’re a beer drinker, you will be pleased with their unusual collaborations with Three Floyds. The "Underground Goat," their private dining space below the restaurant, is one of the most sought-after party venues in town."

The Publican

American restaurant · West Town

"Dining at The Publican is always a treat. It’s kind of the ideal menu, with oysters, roast chicken, fries, and lots of delicious sides. The room is big and light and open, plus, many booths have little saloon style swinging doors on them for privacy. Their butcher shop and cafe (Publican Quality Meats) is next-door, and offers a full butchery plus sandwiches and old-fashioned breakfasts; it can be converted into a dining room in the evening for private events."

Boka

American restaurant · Lincoln Park

"A few years ago, the team behind Boka enlisted Simeone Deary Design Group to give the Michelin starred restaurant a top-to-bottom overhaul. The resulting space—an earthy mix of muted mauves, with one wall covered entirely in antique door handles and another in live moss—is the perfect setting for Chef Lee Wolen’s refreshingly unfussy take on fine dining: heirloom carrots, brandade ravioli, and the now famous roasted chicken. The desserts are pretty extraordinary too (see: 70 percent South American cacao mousse). The terrace opens up onto the patio and has doors that close to the main dining room for private events."

Ada Street

Gastropub · Bucktown

"The menu at this hidden gem (it's quite literally hidden near a Home Depot in an unmarked building) remains exciting: gnocchi with maple bacon, steak tartare with fried capers and egg yolk, PB&J bread pudding. In the summer, they open up a garage door in the back of the building to an open-air astroturf patio; head to the back to play a game of ping pong while you wait for your meal. The private dining room here is legendary, too—tucked away near the entrance to the main dining room, it's a popular pick for the film and music crowd."

Eli's Cheesecake Company

Bakery · Dunning

"This is where real Chicagoans go for Chicago-style cheesecake—less dense than NY-style with a moist, butter-cookie crust. There’s a miles-long list of inventive flavors—white chocolate raspberry, hot chocolate, blackberry sour cream—but the original is still tops. Coincidentally, Eli’s is also famous for having the best tofu-based vegan cheesecake in the country, which according to lore, the owners developed after GP suggested there was a hole in the market for vegan cheesecake that didn't taste like cardboard. "

Pequod's Pizza

Pizza restaurant · Sheffield Neighbors

"It’s kind of blasphemous to visit Chicago and not indulge in a deep-dish pizza, and the pan pies at Pequod’s (they’ve been churning them out since 1970) are the best money can buy. Sure the crust is simultaneously crispy and pillowy and the toppings bountiful, but it’s the extra layer of cheese between the dough and the pan that’s helped them stand the test of time. "

RealGood Stuff Co.

Permanently Closed

"This Old Town juicery goes to great lengths to make their cold pressed juices (and smoothies, yogurts, salads, snacks…) live up to its name. A dedicated juice chef takes care of sourcing (all local, always organic), and the hilariously punny names make remembering your favorite blends easy (Juice Springsteen, Punky Juice-ster, Juice-tin Bieber—you get the idea). Plus, the space itself—all white save for the occasional bursts of neon—is nice for a mid-day breather."

Doughnut Vault

Donut shop · River North

"Doughnuts have been enjoying a pretty awesome resurgence, and nowhere is that more evident than this family of bakeries, where out-the-door lines are a daily occurrence. Flavors run the gamut from buttermilk to gingerbread stack, but the award winning glazed is the long-standing favorite. For diehards, it might be worth it to hop from shop, to shop, to truck as the menus and daily specials vary. The truck, for example, serves strictly old fashioneds (check twitter to find out where it’s parked). Keep in mind that all three can shut down unexpectedly if stock runs out. (The other standing location is in West Loop.)"

Blue Door Farm Stand

American restaurant · Sheffield Neighbors

"Part neighborhood café, part grocery, this Lincoln Park favorite is the definition of farm-to-table: All seasonal ingredients for the café and fresh produce for the market either come from the Blue Door farm, which is situated on what used to be Oprah’s property, or a number of other local purveyors. The eat-in menu has six grilled cheese varieties and a selection of craft beers while the small dry-goods section offers house-made pantry stockers and giftables from Chicago Candle Co., and goop-approved Murchison-Hume."

Thompson Chicago

Hotel · Gold Coast

"This boutique hotel feels at once like an urban loft and a cozy cabin, combining rich colors and exposed brick with stellar views of Lake Michigan and the Chicago skyline. Its Gold Coast location means it's just a walk away from shopping and dining on the Magnificent Mile (and legendary pizza from Lou Malnati's), though the admired Osteria Nico downstairs means you don't even have to leave the hotel for Italian with a view. Just as enticing are the modern rooms themselves, featuring velvet seating and Brooklyn-made D.S. & Durga toiletries. If you do decide to change out of the insanely comfortable robes and venture outdoors, though, take advantage of the hotel's complimentary offsite car service."

The Bristol

Permanently Closed

"Don't be fooled by the clean, no-frills setup at this Bucktown bistro, Chef Todd Stein's menu is complex and downright experimental at times. At brunch time, things take a more low-key, but equally satisfying turn with smoked ham benedict, braised pork chilaquiles, and a pork-broth noodle situation hilariously called the hangover breakfast. The sprawling second floor is reserved for private parties of up to seventy-five people. There are two other arrivals from the same company, which both justify a visit: Balena and Formento's."

Mireille's Studio

Skin care clinic · Gold Coast

"Mireille Hamon counts Oprah among her many makeup and skincare clients. The skin guru grew up and received her training in France, which explains her brilliant less-is-more approach. She’s a wizard at clearing blemishes via gentle steams, soothing masks, and careful extractions. Her LED light therapy and microdermabrasion sessions are stellar. And the woman is also an eyebrow genius."

Credo Clean Beauty

Cosmetics store · Bucktown

"This progressive, impeccably curated natural beauty boutique stocks a wide range (more than 100) of nontoxic brands from around the globe, including top skincare and makeup products from de Mamiel, Ilia, Kjaer Weis, Kypris, RMS, Tammy Fender, and our very own goop by Juice Beauty. The original shop debuted in 2015 in San Francisco and quickly gained a huge following. Sister locations have since opened in Manhattan, Brooklyn, Los Angeles, and here in Chicago, where there is an exclusive Tata Harper spa, much like the other locations. "

Cleise Brazilian Day Spa

Day spa · River North

"Owner Cleise Gomes moved to Chicago from Brazil in 2000, and has been working to bring traditional Brazilian beauty techniques to the U.S. ever since. Given her experience and background, it’s no surprise that Gomes is famous for her waxing techniques, but it's her facials that are actually one of the city's best kept secrets. There are glycolic peels, oxygen and LED light therapy, and a face massage-focused session that includes a rousing, heavenly scalp treatment. "

Allyu Spa

Day spa · Goose Island

"Allyu (pronounced eye-you) is the Quechua word for community, and this Riverwalk-neighborhood spa's commitment to community spreads far beyond its clients. Sustainability manifests itself in nontoxic beauty products, cabinets made from reclaimed barn wood, and locally made soaps for sale. Besides a range of more traditional services, the incredible facials incorporate healing grape stem cells, rose-quartz massage, and smoothing enzyme masks, plus an amazing chakra balancing treatment. "

Semicolon Bookstore & Gallery

Book store · Wicker Park

"DL Mullen, the female founder behind Semicolon, one of Chicago’s newest independently owned bookstores, has created a space where the library of titles is immense and the comfort is instant. An afternoon spent browsing books is a lesson in sensory pleasure, with rotating art on the walls, plenty of seating, and gorgeous decorative touches, like bright rugs and literary quotes. It’s the kind of spot where settling in with a stack is encouraged and questions are welcome. Mullen and her team provide thousands of donated books to Chicago public school students, and Mullen (who has a PhD in literary theory) is a seasoned pro at helping reluctant-to-read kids and young adults find books they won’t be able to put down. Images courtesy of Zach Caddy. "

Field Museum

Museum · Grant Park

"One of the country’s great institutions, the Field Museum encompasses about sixty-five million years of natural history, give or take. Dinosaurs are almost brought to life with fully reconstructed skeletons, including the most complete T-Rex frame in the world, and dozens of animated videos and interactive displays create an engrossing narrative of evolution that’s easy for kids to digest. But grownups are just as enthralled. There’s also the Play Lab, an educational space for the youngest visitors to crawl into recreated dinosaur nests, play with toy fossils, and experiment with musical instruments from ancient cultures. The building itself is a neoclassical beauty inspired by the temples of Ancient Rome and Greece, and the location—right on Lake Michigan and adjacent to Grant Park—is perfect for outdoor picnics and running around after a visit. "

Jayson Home

Home goods store · Ranch Triangle

"This beloved vintage furniture/décor/botany mecca was a major contributor to making the Chicago goop Pop the experience it was. Somewhat rare, Jayson Home designs floral arrangements that are as exceptional as their furnishings. Perusing the shop's bright space is always an inspiring experience, but you can also order flowers and plants from their online store for delivery in the Chicago area."

"A native Midwesterner, Frank Lloyd Wright’s Chicago work is easily accessible for architecture nerds in search of inspiration, especially in the Oak Park neighborhood. This is where you’ll find Wright’s own former home and studio, designed when he was just twenty-two years old. While you could happily amble about the leafy streets and see the Robie House and the Harry S. Adams House—two of the most well-known Wright-conceived homes in the area—it’s really his own home place that makes the best starting point. You’ll see features, like his obsession with horizontal lines, cantilevering, and inglenook fireplaces, that would become Wright’s signature in his later projects. It’s a fascinating history lesson to walk through his early experimental, trial-and-error canvas. "

Adler Planetarium

Planetarium · Burnham Park

"In many ways, Chicago is a city made for kids. Parks and green spaces are everywhere, and the museums always seem to have plenty to offer the little ones. Adler Planetarium, right next to the Field Museum on the shores of Lake Michigan, is a prime example. Come here for a fun dose of cosmic escapism (adults will love it, too), where exhibits like “The Universe: A Walk Through Space” is akin to stepping into another world. You’ll wander through darkened rooms illuminated only by high resolution, twinkling recreations of the stars, galaxies, and planets. "

Chill Anywhere

Meditation center · River North

"As the name suggests, Chill is the place to come to escape. It’s a River North meditation studio that breaks the daunting task of quieting the mind into thirty-minute sessions, each designed to calm and reset a specific area of concern. “Breath” is focused on mental clarity and the elimination of brain fog. “Insight” is for the career-minded looking for work dilemma breakthroughs, while “Rest” is for those on a quest for better sleep. There’s even a course for kids, designed to train younger minds to de-stress and find stillness amid jam-packed schedules. "

yogaview Chicago

Yoga studio · Bucktown

"There are yoga studios that teach you to stretch and strengthen, and then there are yoga studios that seem to give you the tools to master mind and body. Lincoln Park’s Yogaview definitely falls into the latter. That’s due to thoughtfully-led classes taught by instructors who somehow manage plenty of individual attention, even in group classes, especially beginner sessions so newbies develop a strong foundation of basics. The expansive studio itself is a calming mix of exposed brick, high wood-beamed ceilings, and warm, soft lighting."

The CryoBar Lincoln Park

Wellness center · Sheffield Neighbors

"The metal cryotherapy tanks found at Lincoln Park’s CryoBar are as futuristic as it gets—and be warned: the thought of being surrounded in a subzero fold of icy fog is a little daunting. But many regulars describe the enveloping cold as a surprisingly pleasant experience, which is meant to release endorphins and produce an anti-inflammatory response that can reduce pain and increase your metabolism. It’s also said to encourage a great night’s sleep. It’s an easy, quick process: Step inside, remove your robe, and after three minutes, you emerge with a body that feels rested and recharged. "

The Second City

Comedy club · Old Town Triangle

"This legendary sketch and improv comedy troupe has churned out some of the country’s best comedians (Joan Rivers, John Belushi, Bill Murray, Tina Fey, and Stephen Colbert—and that’s barely skimming the surface). The group now has a permanent presence in Toronto and Hollywood, but its roots have been firmly planted in Chicago since 1959. You can catch one of their shows any night of the week, but you’ll want to pick up tickets well in advance as shows tend to sell out."

Tied House

Restaurant · Lakeview

"The typical caution against filling up on bread before dinner flies out the window at Tied House, in Lakeview, where Parker House rolls are served with addictive sides like chicken liver mousse, green tomato marmalade, and buttery bone marrow. Some of the best entree options are on the lighter, side, including vegetarian dishes like maitake mushrooms in a shoyu and leek broth that’s packed with umami. If there’s room, though, meat-based items (milk braised pork with cabbage salsify and apple, short rib with black garlic and yellow foot chanterelle mushrooms) is worth the extra calories. "

Lonesome Rose

Mexican restaurant · Logan Square

"In a blue, rectangular clapboard building in Logan Square, the team from Land and Sea Dept., which run popular spots like Lost Lake and Cherry Circle Room, have scored another hit with Lonesome Rose. The decor gives off a Southern California vibe (lots of light wood accents, potted cacti and ficus, and sunlight streaming through oversized windows), but the food is pure Tex-Mex. The chile con queso is probably the best you’ll find in the city (you’ll want to add black beans), and the fried chicken torta with pickled peppers is a winner, too. There’s also a basement bar, Golden Teardrops, convenient when you want an after-dinner drink without having to travel too far. "

Pacific Standard Time

Permanently Closed

"COVID-19 update: Temporarily closed. Pacific Standard Time reminds us of some of our favorite restaurants in L.A. (Botanica, Gjusta, we're looking at you), and it’s clear that chef Erling Wu-Bower took cues from coastal California, both in menu, open kitchen, and modern, light-filled space. Drawing from Mexican, Italian, and Mediterranean flavors, you can expect plates of oven roasted asparagus marinated in black garlic molasses, trout in a fennel-mushroom broth, and margherita pizza with pistachio pesto from a wood-burning oven. For dessert, the huckleberry sundae and the sunflower cotton cake with strawberry syrup are winners. And since it's Chicago, a city that does happy hour particularly well, grabbing cocktails (we go for the rhubarb spritzes) at the bar is a popular way to kick off a visit. Photos: Brian Willette"

Aba

Mediterranean restaurant · West Town

"Hovering above Fulton Market in Ballast Point, Aba is the brand new, 4,000 square foot rooftop restaurant that’s turned into one of the city’s buzziest warm weather hangouts (though with several fireplaces spread throughout, it’ll likely remain a hot spot well beyond the summer season). The best way to tackle the Mediterranean-themed menu is by sharing everything, especially the small plates that includes five kinds of hummus (the avocado and fava bean is our favorite), and the red beet tzatziki with horseradish, dill, and finger limes. For dessert, the frozen Greek yogurt with olive oil and sea salt is simple, but so satisfying. "

Bellemore

Permanently Closed

"COVID-19 update: Temporarily closed. A newcomer to the fine dining scene in Chicago, Bellemore is the latest from chef Jimmy Papadopoulos (of the Eastern European-themed restaurant Bohemian House). The food is as elegant as the surroundings—an enormous dining room with curved leather banquettes, vases of seasonal flowers and greenery, and a long marble bar that’s perfect for solo dining or drinks while waiting for dinner. Plating is an art form here, and entrees, like an oyster custard topped with Osetra caviar, tiny squares of green apple, lemon, and dill, and desserts (rhubarb shortcake with goat’s milk sorbet, pickled green strawberries and crispy farro verde) are almost too pretty to eat. Almost. "

Small Cheval

Hamburger restaurant · Bucktown

"Some Chicagoans swear that Small Cheval has the best burgers in the city. And it just got easier to test the theory since they opened a third location in Old Town, near the Gold Coast and Lincoln Park (the other two are located in the downtown Loop). The burger they’re known for is the “double stack,” two patties with cheddar cheese, dijonnaise, pickles, and two slices of maple-glazed bacon. The food menu is small (hamburgers, cheeseburgers, fries), so don’t come here for a salad. But when you’re craving a summertime burger outside on a picnic table with a pitcher of locally-made Half Acre microbrew, there’s no place better."

Elske

New American restaurant · West Town

"COVID-19 update: Temporarily closed. Chicago hasn’t been immune to the Nordic food craze of the past few years, and it reaches new heights at Elske, a Danish-influenced West Loop restaurant from husband-and-wife team David and Anna Posey (formerly of Blackbird, a few blocks away). The spare, airy dining room is thoroughly Danish, and made warm and inviting with jugs of wildflowers, ferns, and candlelight. The menu, meanwhile, is both curious and comforting, consisting of dishes like fermented black bean agnolotti with morels, sugar snap peas, and sherry and aged duck breast and grilled confit with ember roasted kohlrabi, kraut, and creamed duck fat. After dinner, there’s a huge outdoor fireplace—the perfect place to finish your Pinot Noir. "

Spilt Milk

Cocktail bar · Logan Square

"There’s no shortage of bars worth a visit in Logan Square, but Spilt Milk stands out for its dimly-lit, Prohibition-era mood, with elegant William Morris floral wallpaper and a forty-foot mahogany bar. The menu is short and sweet, and there’s nothing typical about it—we love the Turkish Delight, made with Prairie organic vodka, pistachio, lemon, pineapple and rose petal, but the local beers on tap (including brands like Moody Tongue and Solemn Oath Brewery) provide a few more reasons to stop in. "

Barcocina

Restaurant · Lakeview

"While Mexican fare is the anchor of the Barcocina menu, the food takes cues from other parts of the world, too, like Korea (short ribs with kimchi) and Thailand (a chicken quesadilla with spicy chiles and peanuts). It’s a testament to chef Matt Williams’ skill that everything is equally great, and the large, warehouse-style space is made cozier with communal tables and wood-paneled walls that give off a warm, welcoming feel. There’s a fire pit on the patio for pre- or post- dinner cocktails. Our favorite is the House Fire, made with Cointreau, jalapeno-infused tequila, and the homemade sour mix. "

Federales Chicago

Bar · West Town

"It’s always a good sign when you need sunscreen for lunch. Federales is such a place. It has a retractable roof above a massive patio, serves the perfect spicy-but-not-too-spicy margaritas, and the homemade tortilla chips and guacamole are the kind that could sustain you until tomorrow. It’s the kind of place you want to bring a group of friends—or hell, strangers—and stay for an entire afternoon under the sun. Those lively afternoons turn into even livelier evenings once the tequila starts flowing (there are over forty varieties) and the tacos (adobo shrimp, pulled chipotle chicken) are some of the best in the West Loop. "

"We teamed up with Heritage as part of our Chicago pop last year (we're currently in Sag Harbor, Dallas, and Aspen for the summer). After all, this is the kind of family-run operation that can make all your bike-related dreams come true. Not only will they custom build one from scratch (Tassels? Glitter? No problem!), but they make great coffee, too. The original Lincoln Avenue outpost (owners Mike and Melissa Salvatore actually live upstairs) does both in addition to a sweet general store, while the newer Heritage Outpost in Uptown is devoted entirely to coffee. You'll find free Wifi, and a group of people working on laptops, at both locations."

Dollop Coffee Co.

Cafe · Buena Park

"While Dollop has expanded across Chicago over the past 10 years, it’s still very much the neighborhood coffee house at heart—there’s nothing slick or overwhelmingly modern about any of the cafes. At the original Uptown spot, the seating options include lived-in couches and upholstered chairs, which if you’re in it for the long haul, makes a difference. The food offering, while modest, will do the trick in a pinch. The Streeterville location is spacious and well suited for study groups or casual meeting. Want fresh-baked pie to go with your coffee? Evanston serves Hoosier Mama pie all day. Perfectly brewed Metropolis coffee is consistent throughout so check out the Downtown and Gold Coast outposts, too."

Alinea

Fine dining restaurant · Lincoln Park

"Grant Achatz needs no introduction. The chef has helmed what is arguably the greatest restaurant in America since its 2005 opening (just watch the first episode of Chef's Table season two...there are no words). Alinea has received every accolade going (including a whopping three Michelin stars) but, awards aside, this thoroughly modern restaurant's greatest success is remaining open (and packed to the rafters) for over a decade. Spaced out across a few floors, the beauty of Alinea is choice—sixteen to eighteen courses on the first floor, a more subdued ten courses on the second (wine pairings available with both). The cuisine is on the experimental end which means lots of foam, the odd sprinkling of molecular dust, and a heavy dose of nostalgia mingled with modernity. The perfect example of a signature Alinea dish is the translucent pumpkin pie: that sweet, spiced pumpkin pie flavor distilled into clear gelatin and poured into a tradition pie crust—genius. A recent shake-up means that executive chef Mike Bagale is moving on and veteran staffer Simon Davies—who started in the restaurant as an intern over nine years ago—is taking the reigns. And finally, last year's renovation (aside from knocking down a few walls) meant the freed-up staff travelled the world for gastronomic inspiration—the new menu packs a nuanced, flavorful punch, and the space is a pleasure all its own. (Reservations open the fifteenth of each month.)"

"Chicago-based Intelligentsia ushered in a new wave of gourmet coffee shops, the kind where responsibly sourced and expertly roasted coffee is prepared using methods that, though time-consuming, result in a pretty perfect cup. As a rule, all outposts are aesthetically unique (five others are scattered in Old Town, Broadway, Millennium Park, Logan Square, and The Loop), offer free Wi-Fi, and have loads of seating options. Plus, you kind of have to love the theme-dressed baristas. "

Schwa Restaurant

New American restaurant · Wicker Park

"The absolute highlight of any Chicago trip is eating at Schwa. Chef Michael Carlson and his staff are so punk rock that they don’t even answer the phone, which makes getting a table difficult, yet weirdly fascinating. From the outside, Schwa looks like it has been condemned. Inside, the dining room is small and spare yet cozy. The formality of the service and menu (no orders taken until the whole party arrives, and the elaborate tasting menu) is juxtaposed by all the hot waiters in skater clothes and the blaring hip hop/heavy metal. The food is sublime. It’s classic American comfort food by way of Ferran Adrià/Banksy/Tony Hawk. It’s off the hook. Try the 9-course tasting menu. "

High Five Ramen

Ramen restaurant · West Town

"According to High Five Ramen, a good bowl of ramen boils down to the broth. Their version is creamy and miso-y with a nice kick. Thanks to generous helpings of chiles and pepper—as the warning on the menu suggests—the restaurant’s signature namesake dish is guaranteed to set your mouth on fire. If you like your noodles a little less intense, try the no-spice version or the “Special” ramen. Though there are only sixteen seats, the wait is reasonable and the cavernous feel of the space is weirdly romantic. The alcohol offering is pretty skimpy, but the spiked coconut painkiller slushy is really all you’ll need."

Dove's Luncheonette

Diner · Wicker Park

"COVID-19 update: Temporarily closed. A working jukebox, padded stools, and counter seating…aesthetically speaking, everything about this smallish Wicker Park restaurant screams retro luncheonette. The menu, on the other hand, is the farthest thing from greasy diner food. Chef Ryan Piotrowski turns out an impressive selection of Southern-inspired Mexican comfort food (red chile enchiladas, grits, and a bunch of yummy chicken dishes) and a tequila-heavy drink menu to match. The seating situation is a tad unconventional and doesn't really accommodate large groups comfortably. That said, it’s ideal for a low-key one-on-one."

Doc B's Restaurant + Bar (River North)

American restaurant · Near North Side

"This self-professed “fast-casual” eatery prides itself on giving guests a 100 percent customizable experience. The tech-to-table system allows for lightning-fast service (order from a digital menu board, and then take a wireless tracker to your table), though if traditional waiter service is more your speed, there’s that too. Food-wise, the focus is on healthful, fresh fare, with the menus at both locations brimming with veggie-driven dishes (for the most part, produce is sourced locally) like kale slaw and grilled artichokes, in addition to comfort staples like matzo ball soup and close to a dozen burger variations (the turkey burger is a GP favorite). There's also a location in Gold Coast."

Little Goat Diner

Diner · Lakeview

"This is Stephanie Izard's elevated riff on the classic American diner, so expect to find vinyl booths and all-day breakfast—but know that it’ll be the farthest thing from rubbery eggs and soggy toast. It's more like spaghetti and clams, kimchi bacon & eggs, and a savory bull’s eye French toast. For lunch, go for the build-your-own burger and side of smoked fries…this is a diner after all. There’s a strict walk-in only policy, so be prepared for a wait. "

Gilt Bar

Restaurant · River North

"The first thing you need to know about Gilt Bar is that it’s not a bar—it’s a full-on restaurant, with a pared-down menu of small-plates that rarely eclipse the $20 mark. Here you’ll find pork meatballs, ramp risotto, and steak tartare served on toast. What’s more, there is an actual bar downstairs. It’s called Curio, and with its candlelit, subterranean vibe, and impressive classic cocktail selection, it’s arguably the best date spot in town. "

Bavette's Bar & Boeuf

Steak house · River North

"Like most establishments on Brendan Sodikoff’s roster (Au Cheval, Gilt Bar), the décor at this River North steakhouse is old time-y and darkly romantic (tufted leather booths, hard-wood floors, vintage mirrors) with a dinner offering that clearly values tradition over pomp: meatloaf, crisp wedge salad, and really really good steak frites. Wash it all down with something from the classics-minded cocktail list (regulars tend to go for the Dark & Stormy)."

KAI ZAN

Japanese restaurant · West Town

"Collectively, twin chefs Carlo and Melvin Vizconde have spent fifteen years honing their craft at respected sushi establishments before striking out on their own. So yeah, the backstory of this BYOB twenty-two seat sushi spot is just as interesting as the innovative offering of esclar-wrapped oyster clouds, duck skewers, and all manner of sashimi. At $60, the omakase menu is a good way to sample the best of the best."

Parachute

Korean restaurant · Avondale

"This Avondale forty-seater got its start from a Kickstarter campaign and is operated by Top Chef alum, Beverly Kim, with help from her husband, fellow chef Johnny Clark. Their Americanized take on Korean staples (pork belly and mung bean pancake, Spanish mackerel Bi Bim Bop, house-made kimchi) has proven to be a huge hit with locals who are encouraged to come in with family in tow and ask for the thoughtfully developed kid’s menu. "

Maude's Liquor Bar

Permanently Closed

"It may be billed as a bar (and yes, the cocktails are something else), but there’s a lot more to Maude's than that—mainly, the fact that it has a full dinner menu. On offer you’ll find expertly prepped French classics (escargot, French onion fondue) as well as a great selection of fresh oysters. The space is on the small side, but the exposed brick walls and dim lighting make it exactly the kind of place you’d want to tuck into for a cassoulet on a cold night…followed by the crème brûlée."

Mirai Sushi

Sushi restaurant · Streeterville

"Unfussy" is probably the best word to describe the fresh fish at this sexy little sushi joint. All the chefs are traditionally trained, so while the more out-there rolls and daily specials are great, it’s the beautifully cut sashimi and nigiri that steal the show. It’s also important to note that while the offering is topnotch, the atmosphere is decidedly low-key, just right for a weeknight dinner. Both this location and the Wicker Park outpost offer delivery and takeout."

The Aviary

Cocktail bar · West Town

"How could we do a Chicago guide without mentioning Grant Achatz, the Midwestern wunderkind of molecular gastronomy? His restaurant, Next, and bar, The Aviary, are tops in our book. Expect flavors, textures, and combinations that you’ve never encountered before. Next is an interpretation of French cuisine harkening back to 1906. The Aviary is more than a cocktail bar or lounge. It’s a lab. To get a coveted reservation (or a ticket, as the website indicates), sign up online."

Riccardo Trattoria

Italian restaurant · Lincoln Park

"This is the kind of authentic Italian standby that has no need to futz with the basics. Everything, whether it’s a seasonal pasta or ossobuco, is prepared perfectly and true to tradition, the way chef Riccardo Michi has been doing it for years (go if you're especially hungry, as portions tend to run large). "

avec Restaurant

Mediterranean restaurant · West Loop

"Avec is one of Chicago's enduring food destinations. It boasts a sleek all-wood interior, and rows of communal tables that aren't exactly comfortable, but do the job (particularly because long lines dictate that you shouldn't exactly linger). It’s technically a wine bar, so there’s an extensive wine list in addition to a selection of beers and cocktails. Food-wise, the menu is broken up into shareable plates that range from charred octopus to stuffed dates, and large plates like confit chicken paella and whole roasted fish."

Au Cheval

American restaurant · West Town

"Exposed brick, leather banquettes, and mood lighting make this the ideal date spot—whether it’s of the romantic or friendly variety. They don’t take reservations, so we suggest cozying up at the bar for a classic burger (many say it’s the best in town) and a cold beer (there are tons of domestic and international options). The brunch shouldn’t be missed—the fried house-made bologna sandwich with a side of hashbrowns is the restaurant’s most popular order."

Athenian Room

Greek restaurant · Sheffield Neighbors

"This beloved neighborhood haunt is one of the best family-friendly meals in town. The menu is packed with tasty dishes that are just simple enough to accommodate a kid’s palate. The roasted chicken in particular seems to net the most acclaim from diners both big and small."

Chicago Q

Barbecue restaurant · Near North Side

"By far the best BBQ in Chicago. The menu is short and, unsurprisingly, meat heavy but what makes Q special are the house wood-smoked meats and the distinctive rubs and pickles they concoct so consistently."

Arami

Japanese restaurant · East Ukrainian Village

"This West Town gem has some of the freshest sushi in town. The Japanese dishes here—uni shooters, sashimi, nigiri—are all authentically modern, a testament to chef Nelson Vinansaca."

Longman & Eagle

American restaurant · Logan Square

"COVID-19 update: Temporarily closed (though, the inn is open). This is another great Chicago gastropub that has pretty impressive and rarified food and drinks. There are also a few very affordable and sleekly decorated guestrooms, featuring the work of some great American craftsmen and designers, just upstairs."

Longman & Eagle

American restaurant · Logan Square

"COVID-19 update: Temporarily closed (though, the inn is open). This is another great Chicago gastropub that has pretty impressive and rarified food and drinks. There are also a few very affordable and sleekly decorated guestrooms, featuring the work of some great American craftsmen and designers, just upstairs."

Piccolo Sogno

Italian restaurant · Fulton River District

"A collaboration between a chef and a wine connoisseur, Chef Tony Priolo and Ciro Longobardo opened Piccolo Sogno in 2008. The modern and rustic Italian food is all about the freshest, seasonal ingredients and Italian wines. The best seats in the house, especially in the summer, are in their quiet outdoor patio."

RL Restaurant

American restaurant · Magnificent Mile

"RL Restaurant (yes that’s RL for Ralph Lauren), has the old-fashioned feel of an English club, with dark paint on the walls, leather seats, and art arranged salon-style on the walls. It’s a prime spot for ladies who lunch. Stop by for their chopped salads, club sandwiches, and tomato soup."

Parson's Chicken & Fish

Chicken restaurant · Logan Square

"As the name suggests, you can come here for excellent chicken and fish, both fried to perfection and not at all greasy. But an emphasis on booze is to be expected from the guys that brought you Longman & Eagle. The bar stays open till 2am nightly (3am on Saturdays!) and serves craft cocktails and beer on tap, as well as a lethal Negroni slushy. They also make excellent use of the outdoor space (complete with freestanding bar and ping-pong tables) which functions as a patio in summer or an ice skating rink in the colder months."

Big Star

Mexican restaurant · Wicker Park

"Unlike so many of the city’s more popular watering holes, this indoor-outdoor Tex-Mex spot is bright, airy, and massive in size. It’s part of One Off Hospitality Group (Dove’s Luncheonette, Avec) and as evidenced by the deep tequila/beer/cocktail list and 2am closing time, values a good time above all. To balance out the copious amounts of booze, order tacos and lots of guacamole from the walk-up window—it's usually faster than waiter service."

ikram

Women's clothing store · Near North Side

"Ikram is an incredibly special store with everything handpicked by Ikram Goldman, the owner who is known for, among other things, having styled Michelle Obama. The sprawling space itself is pretty impressive, with a dedicated home goods shop, gallery, and cafe on the second floor. Same goes for the one-of-a-kind clothing, accessories and spectacular jewelry on offer from such lauded names as Lanvin, Manolo Blahnik, and Tom Binns. Also, come here to shop new designers you've probably never heard of before and fun collaborations."

Penelope's

Clothing store · East Ukrainian Village

"Not counting department stores, it’s not often we find a shop where every member of the family is guaranteed to leave happy. For husband-and-wife team Jena Frey and Joe Lauer, the trick is to stock their Ukrainian Village boutique with cool, well-designed lines that they themselves want to wear—A.P.C, Me and Arrow, and Sessun for women; Brooklyn Tailors, Mollusk, and Norse Projects for guys; plus a small but mighty selection of beauty-shelf staples from Herbivore Botanicals and Plant. And while there isn’t a ton for kids, the stuff that’s available—Petit Bateau onesies, Hansel from Basel socks—is all pretty much perfect. "

Asrai Garden

Permanently Closed

"After picking up a gig at a local florist’s, college dropout Elizabeth Cronin fell hard for the craft and at 23, went out on her own. Over the 15 years she’s been in business, her space evolved into a goth-ish, fairy tale nook for everything from jewelry (Catbird, Ariko, and local Sarah Shikama are just a few standouts) to home décor (Santa Maria Novella candles, Leah Ball pottery) to vintage taxidermy—all deftly mixed with the fresh blooms that started it all. Photos: Dan Paz"

Merz Apothecary

Pharmacy · Lincoln Square

"Stepping in here is the closest thing to time travel. Peter Merz opened this North Side institution in 1875 to resemble the European apothecaries his customers were missing, and other than moving to a bigger space in the 80s, it really hasn’t changed much: Holistic remedies and herbal tinctures (rounded out by a massive selection of vitamins and supplements) are displayed in their original antique jars, while natural skincare and beauty products from modern day favorites like Dr. Hauschka, Klorane, and Jao line the shelves. There’s also an equally well-stocked downtown location. "

Humboldt House

Home goods store · Humboldt Park

"Owner Claire Tibbs puts a lot of love into staging the beautiful range of vintage modern furniture, ceramics, textiles, and jewelry as a series of vignettes, making this sprawling space that much easier to navigate. It also means you get a pretty convincing preview of what, say, a retro brass bar cart or Hans Olsen leather chair might look like in your own home. On a smaller scale, the selection of local-designed jewelry, home goods, and apothecary items is as easy on the eyes as it is on the wallet. "

Notre

Men's clothing store · West Town

"Spotlighting what they describe as “well-built, aesthetically driven goods,” the guys responsible for this Andersonville menswear standby have nailed the elusive not-trying-too-hard vibe. The shop offers a thoughtful mix of luxe lines (A.P.C., Common Projects, Steven Alan) and classic standbys (Filson bags and Red Wing Heritage boots), but what sets them apart is their penchant for seeking out unique collaborations, like exclusive knits from S.N.S. and a sizable selection from the Barbour x White Mountaineering line."

Salvage One

Antique furniture store · West Town

"Navigating this colossal salvaged furniture and décor warehouse is actually surprisingly easy, especially if mid-century modern is your design sweet spot. Inventory is updated pretty much daily so no two trips are alike. Conveniently, they also offer carpentry services at the on-site workshop, making this an excellent resource for decorators and designers. Plus, the lush courtyard is an easy sell as a popular special event and wedding venue. "

SPACE 519

Women's clothing store · Streeterville

"In just a few years, owners Lance and Jim have made a name for themselves for their impeccable taste, and for bringing otherwise-unknown designers and brands to their shop on North Michigan. Their tastes run the gamut from post-pop ceramics by Seletti, to tongue-in-cheek stationery, to Building Block tassel bags, Rachel Comey trousers, and Markus Lupfer sweatshirts: In their words, “it’s a general store that’s anything but general.” In the beauty department, find everything from Binchotan charcoal masks, to the full range of goop clean skincare. "

Sprout Home

Garden center · West Town

"It’s true that here you’ll find all manner of fresh flowers and gardening tools—they’ll even help black thumbs figure out how to revive dying houseplants—but it’s the custom terrariums that make the original Sprout Home a must-see (there’s a second location in Brooklyn, NY). In addition to botany-related workshops and wedding florals, professional garden-design services (there’s a mini nursery in the back) are also available. "

RR #1 Chicago

Gift shop · East Ukrainian Village

"Housed in what used to be a 1930s apothecary (thankfully, the original wood paneling was left untouched), RR#1 Apothecary is one of those stores that you’ll have a hard time leaving empty-handed. On offer: a dizzying array of candles, teas, and soaps, as well as kitschy prank gifts, tea towels, and novelty books. It’s pretty ideal for picking up a last minute something for the hostess, they'll even gift-wrap your selection right at the counter."

Broadway Antique Market

Antique store · North Edgewater

"Chicago antique malls are the stuff of mid-century modern legend, and BAM is the crème de la crème. At 75-vendors strong (most with a focus on Art Deco, Mission, and Mid Century modern design), it’s got something for everyone. Furniture, clothing, accessories, costume jewelry—all of it blessedly organized so there’s little need to dig. And as locals will tell you (or more likely, not tell you) the semi-annual sales are epic. "

Robin Richman

Clothing store · Bucktown

"With its almost exclusive focus on lesser-known European lines (tiered dresses by Tsolo Munkh, Elena Dawson separates, Guidi boots), this Bucktown shop has been a hit with the avant-garde crowd since the '90s. The airy, welcoming space is really more gallery than store, which makes sense since the buy is largely of the architectural and one-off variety. "

Eskell

Home goods store · Bucktown

"Kelly Whitesell and Elizabeth Del Castillo, the founders of this Wicker Park standby, are known for their trend-driven, yet somehow totally timeless sensibility, which is perfectly reflected in the boutique’s easy-to-navigate layout and eclectic buy (Judi Rosen denim, knits from Barcelona-based Yerse, and In God We Trust charm necklaces). And while the eponymous house line might skew a little young for some, for the right girl, the racks of retro-tinged dresses and printed separates are a sartorial goldmine. The apothecary, however, is a sure bet for just about everyone—think, D.S. & Durga fragrances and Qualitas candles."

Moncler

Boutique · Gold Coast

"Maybe it’s because it’s so damned cold in Chicago in the winter that the Moncler store here is one of the best in terms of selection. The Italian brand is famous for making winter outerwear, even big puffy jackets, look good."

Circa Modern

Antique furniture store · East Ukrainian Village

"A former architect and auctioneer, respectively, Jared Peterson and Don Schmaltz partnered up to open one of Chicago’s best furniture showrooms in West Town. This is the kind of place where American, Scandinavian, and Italian mid-century modern designs attract interior designers and new home buyers from around the city. You’ll find Eames chairs, Arne Jacobsen flatware, and more obscure finds (there’s an Alvar Aalto tea trolley, for instance), but it’s a good idea to browse the website before making an appointment at the store: Some may not be ready in the showrooms, but a quick call or email ensures that whatever you’d like to see is brought from the warehouse to the shop for your perusal. "

The Robey

Hotel · Bucktown

"Perched inside the only skyscraper for miles, this new Wicker Park hotel not only boasts killer views of downtown, it's located on one of the best intersections in the city—at the corner Damen, Milwaukee and North Avenues, it's just steps from Big Star, Dove’s Luncheonette, Eskell Boutique, and the Damen Blue Line stop. The building itself is an art deco jewel that preserves much of the charm of its 1920s design, and its triangular footprint means each of the hotel's 69 rooms are filled with plenty of light. Their 13th-floor rooftop lounge, Up & Up, is a great place to grab a drink, too. "

The Art Institute of Chicago

Museum · Grant Park

"Founded in 1879, the Art Institute of Chicago is hands down one of the city’s oldest treasures. The permanent collection is 300,000-strong, boasting such American classics as Grant Wood's American Gothic and Edward Hopper’s Nighthawks. If you haven’t been in a while, it’s worth a visit just to see the recently opened, Renzo Piano-designed Modern Wing. Piano is famous for his lighting, and the shelter above the space (which allows some daylight to sift into the galleries) is one of the best examples of his work to date."

Museum of Contemporary Art - Chicago

Modern art museum · Streeterville

"Housed in a Josef Paul Kleihues-designed building in the heart of the city, MCA Chicago is one of the best contemporary art museums in the world. In years past, they've organized everything from the first David Bowie retrospective, to the US debut of Colombian sculptor Doris Salcedo, as well as a major survey of American painter Kerry James Marshall (which they co-organized with the Met and LA's MOCA). We also love MCA for its manageable size—you can easily traverse the major galleries in a couple hours."

Sable Kitchen & Bar

Permanently Closed

"COVID-19 update: Temporarily closed. Located in Hotel Palomar, Sable is the destination for a few drinks or a full meal. They serve gastropub dishes with an American twist, and a long list of wood-fired flatbreads. Their 14-page cocktail menu is garnering plenty of attention, too, for its mix of old-fashioned drinks (a long list of options for a good old Martini) and new twists (Ice & Fire, for example, is a tequila-based drink with Sriracha, cucumber, agave, and fresh lime)."

Nico Osteria

Italian restaurant · Gold Coast

"COVID-19 update: Temporarily closed. Nestled a stone's throw from Nico Osteria at the Thompson Hotel, this upscale lounge leans heavily on low-proof drinks (juleps, spritzes, and the like), meaning you can indulge without getting too sloppy. One of Nico’s most prominent design features, other than the luscious stretch banquette and pops of jewel tones, is a plant wall which, in addition to lending a dreamy indoor-outdoor quality to the space, absorbs noise. "