I didn’t plan to fall in love with Chicago. My flight got canceled, and I ended up with an unexpected overnight layover.
But instead of sulking in an airport hotel, I ventured into the city, and wow, was that the right call! A quick walk turned into a spontaneous adventure: skyline views from the riverwalk, live music drifting through Millennium Park, deep dish pizza that changed my life. I left wondering why I hadn’t booked a real trip there in the first place.
Now, Chicago is set to break all-time tourism records this summer, and it makes perfect sense. If you’ve been thinking about a U.S. city escape that combines big energy with chill lake vibes, this is it.
Here’s why you should experience Chicago in summer 2025:
Record Flights, Easy Access: It’s Never Been Easier to Get There
Chicago’s accessibility this year is off the charts. Both O’Hare and Midway International Airport are gearing up for their busiest summer ever, with nearly 17.8 million departing seats expected between June and August, according to the Chicago Department of Aviation.
That means more options, better prices, and new routes, including exciting additions like Madrid, Naples, and even Reykjavik.
Major airlines like American, United, and Southwest are all in expansion mode, so getting to Chicago from almost anywhere is a breeze this year. If you’re flying domestic, you’ll be spoiled for choice. If you're flying internationally, you'll likely find direct connections you didn't have before.
Pro tip: Once you land, skip the expensive ride share and hop on the CTA ‘L' train, O’Hare connects via the Blue Line, and Midway via the Orange Line. It’s cheap, fast, and drops you straight into downtown.
Festivals, Food, and Fireworks: Chicago’s Summer Calendar Is Wild
There’s something about summer in Chicago. The city transforms into one giant outdoor festival, with events nearly every weekend and free concerts in the park that make you forget you’re in the middle of a major metropolis.
Here are just a few events on my radar for 2025:
- 🎸 Lollapalooza (July 31–Aug 3): Olivia Rodrigo, TWICE, Korn, and Tyler, The Creator are all headlining this year. Enough said.
- 🎷 Chicago Blues Festival (June 5–8): A free, multi-stage celebration of the city’s legendary blues legacy.
- ✈️ Air & Water Show (Aug 16–17): Fighter jets and stunt planes soar over Lake Michigan, and it’s totally free.
- 🏁 NASCAR Chicago Street Race (July 5–6): Racing through downtown streets? Only in Chicago.
You can also catch smaller neighborhood gems like Andersonville’s Midsommarfest or Wicker Park Fest, where you’ll find amazing food, local bands, and that down-to-earth Chicago community vibe.
My Spontaneous Visit Turned Into a Full-On Obsession
The first thing I did when I landed unexpectedly? I headed to Millennium Park. I took the usual selfie at The Bean (aka Cloud Gate), wandered through the gardens, and ended up listening to a string quartet play under the stars.
That was the moment I knew this wasn’t just another city.
A few things I always recommend now:
- 🚤 Architecture River Cruise: The best way to see Chicago’s jaw-dropping skyline and learn about the city’s wild architectural history.
- 🎡 Navy Pier: Ride the Centennial Wheel at sunset. The views of the lake and skyline are unreal.
- 🏙️ 360 CHICAGO or Skydeck at Willis Tower: Both offer panoramic views, but I’m partial to 360 CHICAGO because of the lakefront views and the TILT ride if you’re feeling brave.
Get Outside: Chicago's Waterfront and Neighborhoods Shine in Summer
Chicago knows how to do summer right. The Lakefront Trail is an 18-mile path along Lake Michigan, perfect for biking, walking, or just people-watching. You’ll pass beaches, parks, and skyline views that rival any coastal city.
Some of my favorite neighborhood experiences:
- 🛶 Chicago Riverwalk – You can rent a kayak or just grab a cocktail and watch the boats go by.
- 🎨 Pilsen – A colorful, mural-filled area with incredible Mexican food and art galleries.
- 🍽️ West Loop – Packed with restaurants and rooftop bars, it's a foodie dream.
Speaking of Food: Come Hungry (and Maybe Stretchy-Pants Ready)
No matter how long your trip, food should be part of your itinerary. Start with the classics:
- 🍕 Lou Malnati’s, Giordano’s, or Gino's for deep dish.
- 🌭 Portillo’s for the ultimate Chicago dog—no ketchup!
- 🥩 Mr. Beef (aka the The Bear place) for Italian beef.
Want something more elevated? Try rooftop dining at Cindy’s (insane Millennium Park views) or Aba in the West Loop.
And if you’re indecisive (like me), book a food tour. They’re super fun and give you a crash course in the city’s food scene.
This Is The Summer to Be in Chicago
Summer 2025 is set to be historic for Chicago tourism.
And while the stats are impressive, the real magic is in the experience: a spontaneous jazz performance in the park, a slice of caramelized crust pizza, a rooftop sunset that makes you feel like you’re in a movie.
So, whether you’re booking a full trip or just taking a gamble on a long layover, go!
Be part of the energy. Wander the neighborhoods, eat too much pizza, and fall a little in love with the Windy City.
I know I did.
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Opinions expressed here are the author’s alone, not those of any bank, credit card issuer, hotel, airline, or other entity. This content has not been reviewed, approved or otherwise endorsed by any of the entities included within the post.