Looking to explore Chicago? Discover the best things to do in Chicago this summer this summer from a longtime Chicago resident! Cheers, Chicagoans – it’s officially summer! Okay, so it’s not technically summer until June 21st, but let’s get the celebrations started early now that it’s finally getting nice outside. This is my 6th summer in Chicago, so I’ve had the fortune of exploring so many of the fun summer activities Chicago has to offer, and I’m looking forward to trying a few new things too.

For those of you who are visiting Chicago in the summer (or working on your own summer bucket list!) here are the best things to do in Chicago this summer to try! I may be biased, but these are some of the places I love to eat, drink and explore every time it’s beautiful in town. A few of them are even bright spots during the brutal Chicago winters too 😉

The Ultimate Guide to the Best Things to Do in Chicago This Summer

After a very long winter, Chicago comes alive in the summer (and people start smiling and being friendly again!). After feeling pent up, everyone finds an excuse to be outside – whether it’s a quick walk around Millennium Park over lunch, catching a movie in the park, or seeing some of the amazing outdoor concerts – Chicago has a lot to offer this time of year. Below are the best things to do in Chicago this summer, including the best places to drink, eat and explore.

• Chicago Riverwalk: Speaking of, the Chicago Riverwalk is new, improved and the perfect path to explore the heart of the Loop. I usually like to stop at City Winery for a glass of wine on the way (of course…) and it’s always a blast sitting on the patio by the river.
• Summer Festivals: Every weekend there are a handful of festivals around the city, and I swear they get better every single year. Here’s a line up of this years festivals – and I’m especially looking forward to greek fest (always a favorite!), Taste of Randolph to see Mayer Hawthorne, Pitchfork, and of course, Lollapalooza.

• Go on the Chicago architectural tour: While it’s definitely touristy, I try to go on the Chicago Architecture Boat Tour at least once a summer because the views of the city are so beautiful (and I always learn something new every time). Find a sunny day (bring sunscreen!) and enjoy learning more about the downtown and riverwalk.

• Millennium Park Movie Series: I LOVE that there are movies and concerts in Millennium Park all summer long, and there’s such a good lineup this year! Definitely get there early (5/5:30 if you can), bring a blanket and dinner (I usually pick up sweetgreen which is super close!)
• Farmer’s Markets: There are a few farmer’s markets in Chicago I love, but my two favorite are the Lincoln Park’s Green City Market on Saturday across from the J.Parker hotel, and the Logan Square farmer’s market on Sunday mornings.

• Catch a Cubs or White Sox game: Sports, sports!!! Chicago has a lot to offer in the sports department, and there’s nothing better than taking in a Cubs or White Sox game on the weekend or after a long day of work. You can find the White Sox schedule here, and the Cubs’ here!
• Concerts: There are SO many concerts happening in Chicago this summer, and my friend Lauren rounded up some of the best ones in the coming months! Check out her article here to get the full list – I’m already bookmarking a few myself.
• Randolph Street Market: I love a good market, and Randolph Street has been known as the most beloved antique furniture and decor market in the Chicago area. They’re open only one weekend a month, so make sure to check out the schedule to plan your trip accordingly!

• Summertime Happy Hour: Now that everyone wants to go outside again, happy hours are popping in the city! There are so many fun places to go, but below are a few of my favorite recommendations:
  • Check out London House hotel’s insanely beautiful views (see the picture above of the Wrigley building from the rooftop!) and tasty cocktails. It gets pretty packed (even on weekdays) so make sure to hustle out of work early to get a table and the best view.
  • Cindy’s rooftop also has an incredible view of Millennium Park, and it’s nestled on top of the Chicago Athletic Association. It’s the perfect place for brunch, happy hour, or for some fun games in their game room too! Here’s a review I shared a last year that has some of the highlights of the bar and menu faves!
  • Big Star is my favorite place for margaritas in the city (the tacos are amazing too, but L’Patron has my heart for the best tacos in the city!). I love sitting on their patio on a weekend afternoon or for a many margarita-filled happy hour after work.
  • The Robey in Wicker Park is another favorite spot for happy hour drinks and snacks – and rather than a view of the Loop you can see the skyline and the 6 corners, the heart of Wicker Park. The drinks are delicious – and if you need more than snacks, their restaurant on the first floor is super tasty for dinner or brunch.

• A few other favorite things:
  • Eataly for delicious food, tasty wine and cocktails and the fanciest, fresh Italian groceries
  • Restoration Hardware’s 3 Arts Cafe for the views, food, and of course, lust-worthy funiture
  • Wells Street Food Market food hall opening up in late June (after we patiently waited for many months!) including two of my favorite quick restaurants – The Chow Brothers pierogis and Fare foods that offers a tasty selection of vegan, gluten-free and healthy foods!

Phew! Okay, that was a long list, but I promise they are truly some of my favorite places and things to do in the city! Do you have your own list of the best things to do in Chicago this summer? I’d love to know your picks and anything I might have missed. I’ll make sure to add them in and make updates throughout the summer too. xx