Best things to do in Chicago in the summertime every day of the week

  1. Monday- Happy Hour at a rooftop bar downtown
    There's a lot of great rooftop bars downtown, and with happy hour coming back to life it's a perfect night to take in those good views. ROOF on theWit is probably the most well known of them, but plenty of spots abound. Raised at 1 W wacker wins my current fave with artisan cocktails that you almost feel bad drinking.
  2. Tuesday- Movies in Millennium Park
    Different from the Chicago park district, millennium park plays movies at the pritzker every Tuesday night. Arrive early, because seating matters. And don't be a dick and bring huge chairs like the normal camping ones- then no one around you can see. CPD also has movies all over the city every night, so check the listings for ones near you. Some are family friendly (Ferris Bueller's Day Off), but some aren't (Silence of the Lambs). Check the schedule in advance.
  3. Wednesday- Symphony in the Park
    In the pritzker pavilion, every Wednesday night from mid June to mid August the grant park symphony plays. Since its music, no need to see anything, and the sound system built in means every seat is good. Must bring items- blanket, white wine, good cheese, other assorted food, friends. No matter how awesome you think your set up is, someone will one up you. They also have symphony on weekends, but it's more crowded and there's lots of other great things to do that you can't during the week.
  4. Thursday- catch a ballgame at either Wrigley or the cell
    If you go to Wrigley you might be playing hookie as they have a ton of day games, but it's also a summer tradition. Regardless of where your baseball allegiances lie, both are good ballparks in their own right. Wrigley (home of the Chicago Cubs) is older and has a ton of charm (though also has a circle trough that my husband complains about). U.S. cellular field (White Sox) is newer with modern amenities. Besides, how cool is it that we have two teams to watch?
  5. Friday- grab a drink at your favorite outdoor beer garden (Mine is Moody's pub in edgewater)
    Moody's is the only thing I could ever leverage to get my friends to visit me when I lived in edgewater. It's no frills; service is usually pretty bad, and while they ask how you want your burger cooked there's really no guarantee what you'll get. And yet it is still amazingly charming. The burger and fries are delish, no matter how it's cooked. It's still fairly cheap, but can get crowded in the summer, especially around peak meal times, so be prepared to wait or go early/later.
  6. Saturday- spend time at the beach (or, take in a local festival)
    Chicago made an intentional decision to keep our most valuable land all public access, so there's miles of uninterrupted shoreline. Everyone has their preferred spot (I avoid North Ave beach) but whether you want to relax on the south side near promontory point, get a drink at oak street beach, or rent a paddle board at Loyola or Hollywood beach, there's something for everyone. If beaching really isn't your thing, there's multiple festivals every weekend downtown and all throughout the city.
  7. Sunday- Summer Dance Chicago
    Every Friday/Saturday/Sunday, Summer Dance Chicago happens in the Spirit of Music Garden in Grant Park (601 S Michigan Ave). Sunday is from 4-7. A different style of music and dance every night, so you get to learn some new movies! The first hour is lessons, the rest is open dance. Be ready for lots of random partners to ask you to dance, but not in a skeezy way like they did Saturday night. Go with or without a partner; you'll still have fun.