Summer fun in Chicago is unmatched. There’s something about the combination of big-city energy, lakefront breeze, and long sunny days that makes you feel like anything is possible. Whether you’re into art, food, nature, or architecture, Chicago in the summer has something special waiting for you.
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Let me take you through a day (or weekend) of some of my favorite things to do in the city when the sun is shining and the vibes are high.
Mornings at the Museum: The Art Institute and Beyond
I like to start my summer days in Chicago with a mix of culture and coffee. One of my go-to spots is the Art Institute of Chicago. It’s not just a museum, it’s an experience. Home to iconic works like “American Gothic” and Monet’s Water Lilies, the Art Institute is one of the top museums in the world, and it’s right here in the heart of the city.
Hot tip: Arrive right when it opens to beat the crowds. Grab a latte from a nearby café (I love Goddess and the Baker) and stroll over. If you’re traveling with kids or just looking for something more interactive, the Museum of Science and Industry and Field Museum are also incredible. I’ve spent full afternoons exploring the U-505 submarine exhibit and marveling at Sue the T. rex.
Dive In: Visiting the Shedd Aquarium
Just a short walk from the Field Museum sits one of Chicago’s most beloved attractions: the Shedd Aquarium. It’s more than just a place to see fish, it’s an immersive underwater adventure. I’ve been going to the Shedd since I was a kid, and every visit still feels exciting.
One of the most mesmerizing exhibits is the Caribbean Reef, where you can watch scuba divers interact with rays, sharks, and sea turtles. Don’t miss the Oceanarium, where beluga whales and Pacific white-sided dolphins steal the show. There’s also a great outdoor terrace with views of the lake, perfect for taking a breather while enjoying the skyline.
Pro tip: Buy your tickets online ahead of time to avoid the long lines, especially on weekends.
Lakeside Vibes: Walking, Biking, and People-Watching
After a dose of art and history, it’s time to head outside and enjoy what Chicago does best in the summer: lakefront life.
The Lakefront Trail stretches 18 miles along Lake Michigan and offers stunning views of both the water and the skyline. You can rent a Divvy bike or take a leisurely walk. I usually start at Grant Park and make my way up toward North Avenue Beach, stopping along the way for:
- A snack at the Ohio Street Beach food stands
- Watching volleyball games at Oak Street Beach
- People-watching at Navy Pier (always a scene!)
The breeze off the lake makes it easy to walk for miles without realizing how far you’ve gone. Pack some water and sunscreen, and you’re set.
Views From the Top: Visiting the Skydeck
Once I’ve gotten my steps in, I like to change up the perspective. That means heading up, way up.
If you haven’t been to the Skydeck at Willis Tower, now’s the time. Yes, it’s touristy, but it’s also totally worth it. The Ledge, a glass balcony that extends out from the building, is a bit terrifying but super fun. You’ll get unbeatable panoramic views of the city and beyond, on a clear day, you can see for miles.
Another great option for views? 360 CHICAGO at the top of the John Hancock building. It has Tilt, an enclosed moving platform that tilts you over the edge of the building. Thrill-seekers, this one’s for you!
Lunch Break: Local Eats and Outdoor Patios
By this point, I’m usually starving. Summer is patio season, and Chicago has no shortage of outdoor dining options. Here are a few of my personal favorites:
- Parson’s Chicken & Fish: Casual, fun, and the negroni slushies are legendary.
- The Dawson: Upscale but approachable, with a dreamy outdoor setup.
- Big Star in Wicker Park: Tacos, margaritas, picnic tables, and good vibes.
Whether you want something fast or a long, lazy lunch with cocktails, Chicago’s food scene delivers.
Chill Out Time: Parks, Gardens, and Free Fun
One of my favorite things about summer in Chicago is that you don’t have to spend a lot of money to have a good time. After lunch, I love to slow things down with a visit to a quieter spot.
- Millennium Park: Grab a shady bench and do some cloud-spotting or catch one of the many free concerts.
- Chicago Botanic Garden: Technically just north of the city, but absolutely worth the trip. It’s peaceful, gorgeous, and full of blooms.
- Lincoln Park Zoo: Free admission and super family-friendly.
Sometimes I bring a book and just lounge in the grass. Other times I’ll join a free yoga class or stumble into a pop-up market. The options are endless.
Sunset and Rooftop Drinks
Evenings are when summer in Chicago really shines. There’s something electric in the air as golden hour sets in and locals pour out to enjoy the night.
Rooftop bars are the place to be, and there are SO many good ones. Here are a few of my tried-and-true picks:
- Cindy’s Rooftop: Views of Millennium Park and the lake. Gorgeous.
- The Robey in Wicker Park: More laid-back, perfect for sunset.
- LondonHouse: Elegant and iconic, with stunning river views.
- CloudBar at 360 CHICAGO: You get a drink and a view 1,000 feet in the air.
Grab a cocktail, take in the city skyline, and toast to another perfect summer day.
Why I Keep Coming Back
There’s a reason why summer fun in Chicago never gets old. Even after years of living here and countless visits, I’m still discovering new corners, new events, and new ways to fall in love with the city.
Whether I’m biking along the lake, admiring masterpieces at the Art Institute, or sipping cocktails high above the streets, Chicago always gives me that buzz of joy that only summer can bring.
So if you’re planning a trip or just want to explore your own city with fresh eyes, start with a few of these experiences. And remember: comfortable shoes, layers (this is the Midwest, after all), and an open mind will take you far.
What’s your favorite way to spend a summer day in Chicago? I’d love to hear!
With love,
Bri & Cat
Related Posts you may like:
A Perfect Summer Day in Chicago: Must-See Attractions and Hidden Gems
Visiting Shedd Aquarium in Chicago with Kids: Great Tips, Fun Tricks, and Our Favorite Exhibits
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