"From June to September, The Jay Pritzker Pavilion in the Loop is one of the best places to listen to live music outside. Here, you can listen to a set from Wilco frontman Jeff Tweedy, return for some Tchaikovsky with The Grant Park Orchestra, and then come back on a weekend for Jazz Fest. Outside food and drink is allowed, which makes these concerts perfect for picnics. But if the mere thought of formulating a plan dries out your tongue, you can just grab a beer and bratwurst from one of the surrounding concession stands. Click here for the Millennium Park event calendar. We haven’t been here yet, but want you to know this spot exists." - Team Infatuation