20 things to do in Chicago this summer


There is nothing quite like Chicago in the summer.

It’s our reward for enduring MONTHS of cold, harsh, frankly just rude weather for nearly 6 months out of the year. So when it’s time to sip a cocktail on a rooftop in a sundress, I’M ALL IN!!!

Since returning home last summer, I feel like I’m a tourist in my own city. With new restaurants opening every week and festivals almost every weekend, there’s no shortage of things to keep me occupied. I actually feel like it would take YEARS to fully cover all the summer activities in the city.

I wanted to help locals and visitors alike with a list of my top 20 favorite things to do in Chicago in the summer.

  1. TAKE A STROLL ALONG THE RIVERWALK. The Riverwalk is a 1.25 mile stretch of pedestrian walkway that runs along the south bank of the Chicago River from Lake Shore Drive to Lake Street. It’s the perfect spot for a casual walk that takes you past some of Chicago’s most iconic sites. And when you’re in need of a drink or some food, my fav spots to refuel are Beatnik on the River and City Winery Chicago.

  2. SIP DRINKS AT CINDY’S. All the way at the top of the Chicago Athletic Association Hotel is where you’ll find one of the best rooftop views in Chicago. Cindy’s boasts panoramic views of Millennium Park, the Art Institute and Lake Michigan. And if you want to extend your stay you can book a reservation for lunch, dinner or brunch.

  3. COOL OFF WITH A POPSICLE FROM PRETTY COOL ICE CREAM. With flavors like coffee pretzel toffee and passion fruit hibiscus, how could you not be intrigued by this popsicle shop? And if the artfully decorated pops aren’t enough to get you in the door, how about the crazy cool mural that covers the walls inside? Guess you’ll have to go to see what I’m talking about!

  4. POST UP ON THE PATIO AT ABA. Killer menu, delicious drinks and atmosphere that makes you feel less like you’re in the 3rd largest city in America and more like you’re in a cool restaurant somewhere in the Mediterranean. Aba hits all the marks and it’s the ULTIMATE summer spot. Just be aware, patio is first come first serve.

  5. HAVE AN IMPROMPTU PHOTOSHOOT! There is no better time to take photos in Chicago than in the summer. The weather is nice (in the morning and evenings), the options on where to shoot are endless and honestly everyones doing it for the Gram these days so might as well get on board. My favorite spots to shoot in the city are at the Chicago Theatre, the flower mural on the side of West Town Bakery and the Greetings from Chicago mural.

  6. TAKE AN ARCHITECTURAL BOAT TOUR. This is an absolute must for anyone visiting Chicago for the first time or even locals who’ve never taken the time to learn about the city they call home lol. You learn so much about the city’s history and its unique buildings that make it unlike anywhere else. Plus there’s a full service bar on the boat so that’s a HUGE bonus. Click here for tickets.

  7. ENJOY A SLICE AT PARADISE PARK. Chicago is known for its deep dish pizza. But personally, I’m not a huge fan (I know, I know…kick me out of the city RN for this blasphemy). Instead I love a crispy thin crust pizza, preferably to enjoy all to myself…Anyways Paradise Park is a kitchy trailer park themed restaurant with an incredible patio, cute drinks and insta worthy decor.

  8. GO TO A CUBS GAME. This will come as a shock to most everyone who knows me, but I think going to a Cubs game is one of those things you need to do at least once in your life. Wrigley Field is iconic, the vibe is fun and truly if you think baseball is boring like me, just grab a drink and kick back. Even just going to the bars near Wrigley Field when the Cubs are playing is fun if you don’t want to shell out $$$ for tickets.

  9. RENT A BOAT ON LAKE MICHIGAN WITH YOUR FRIENDS. There is honestly no better way to see the city skyline than on a boat in Lake Michigan. Cruising around the lake is SUPER relaxing and fun in Chicago. Or if you’re trying to get loose and party - hit up the Playpen (the no wake area just south of Oak Street Beach).

  10. ATTEND THE CHICAGO PRIDE PARADE. There’s nothing more fun than celebrating LOVE during Pride Month and Chicago is one of the best places to do just that. Click here for a list of all the events throughout the month.

  11. SIP COFFEE AT MAISON MARCEL. If you summer plans don’t include traveling to the south of France, just hit up this cute Lake View French bakery to eat like you’re in France. Oooo and while you’re at it, make sure to snag a pic in front of the bakery’s colorful mural.

  12. RENT A CABANA AT SHORE CLUB. Grab your gal pals and get ready for a day at the beach with cocktails and snacks at one of Chicago’s best beach hangouts. Or you can grab a sit down meal at the restaurant if sand is not your style.

  13. TASTE OF CHICAGO. This is the festival for foodies and it’s history runs deep. The Taste of Chicago has been taking place for 5 days in Grant Park since 1980. Admission is FREE and you can taste food from some of the city’s BEST restaurants.

  14. SIP DRINKS AT BOLEO. I’ll admit, sometimes Chicago decides it needs to punish us a little, even in the summer, with a sudden, unexpected storm…But don’t let the city’s moody weather dampen your drinking plans. The rooftop bar at the Kimpton Gray Hotel feels like a tropical paradise with its retractable rooftop. Feel like you’ve been transported to Buenos Aires while you drink one of the bars signature cocktails.

  15. RENT A DIVVY BIKE. There’s literally MILES AND MILES of lakefront paths and parks to explore in Chicago. But don’t let the fact that you don’t own your own speed racing bike stop you from getting out and about. Divvy bikes are super easy to rent and only $15 for a day pass. SCORE!

  16. SIP ON A FRUITY DRINK AT LOST LAKE. I love indulging in a fruity drink in the summer and Lost Lake is the PERFECT place to do just that. The banana leaf wall paper and over the top cocktails make it the perfect place to start your GNO activities.

  17. GETTING YOUR SHOPPING FIX AT ALICE & WONDER. I stumbled upon this boutique when I was wandering around Lincoln Park last summer and man am I glad I did. This is easily my favorite boutique in Chicago. The inside of the store is SERIOUS goals with a peacock chair at the back and a gorgeous display in the window, ALWAYS.

  18. GRAB LUNCH ON THE PATIO AT PARSON’S CHICKEN AND FISH. This is a great spot to enjoy a casual lunch and day drink outside (the restaurant serves up this amazing Negroni Slushy you HAVE to try). The restaurant has locations in Lincoln Park and Logan Square !

  19. CATCH VIEWS AND DRINKS AT THE J PARKER. Great vibes, great views, great for out of town visitors. The rooftop bar of the Lincoln Hotel is consistently ranked one of the best rooftops in Chicago and I have to agree. This is a great spot to start or end the night or even Rose all day on the weekend!

  20. BRUNCH SO HARD AT SOMERSET. This Gold Coast restaurant totally lives up to the hype. The decor inside is all kinds of Great Gatsby vibes and the food is just as pretty. Definitely a spot to check out with your gals or your mum!


Be sure to leave a comment or shoot me a DM on Instagram if you visit any of these spots! I’d love to hear what you think! And if you take a picture make sure to share it on social with the hashtag #galsabroad for a feature on my stories!