I didn’t plan to fall in love with Chicago. My flight acquired canceled, and I ended up with an sudden in a single day layover.
But as an alternative of sulking in an airport lodge, I ventured into the town, and wow, was that the proper name! A fast stroll was a spontaneous journey: skyline views from the riverwalk, dwell music drifting by way of Millennium Park, deep dish pizza that modified my life. I left questioning why I hadn’t booked an actual journey there within the first place.
Now, Chicago is about to interrupt all-time tourism information this summer time, and it makes good sense. If you’ve been desirous about a U.S. metropolis escape that mixes huge power with chill lake vibes, that is it.
Here’s why it is best to expertise Chicago in summer time 2025:
Record Flights, Easy Access: It’s Never Been Easier to Get There
Chicago’s accessibility this 12 months is off the charts. Both O’Hare and Midway International Airport are gearing up for his or her busiest summer time ever, with almost 17.8 million departing seats anticipated between June and August, in accordance with the Chicago Department of Aviation.
That means extra choices, higher costs, and new routes, together with thrilling additions like Madrid, Naples, and even Reykjavik.
Major airways like American, United, and Southwest are all in growth mode, so attending to Chicago from virtually anyplace is a breeze this 12 months. If you’re flying home, you’ll be spoiled for selection. If you are flying internationally, you will possible discover direct connections you did not have earlier than.
Pro tip: Once you land, skip the costly journey share and hop on the CTA ‘L’ train, O’Hare connects by way of the Blue Line, and Midway by way of the Orange Line. It’s low-cost, quick, and drops you straight into downtown.
Festivals, Food, and Fireworks: Chicago’s Summer Calendar Is Wild
There’s one thing about summer time in Chicago. The metropolis transforms into one large outside competition, with occasions almost each weekend and free live shows within the park that make you neglect you’re in the midst of a serious metropolis.
Here are only a few occasions on my radar for 2025:
🎸 Lollapalooza (July 31–Aug 3): Olivia Rodrigo, TWICE, Korn, and Tyler, The Creator are all headlining this 12 months. Enough mentioned.
🎷 Chicago Blues Festival (June 5–8): A free, multi-stage celebration of the town’s legendary blues legacy.
✈️ Air & Water Show (Aug 16–17): Fighter jets and stunt planes soar over Lake Michigan, and it’s completely free.
🏁 NASCAR Chicago Street Race (July 5–6): Racing by way of downtown streets? Only in Chicago.
You may catch smaller neighborhood gems like Andersonville’s Midsommarfest or Wicker Park Fest, the place you’ll discover superb meals, native bands, and that down-to-earth Chicago neighborhood vibe.
My Spontaneous Visit Turned Into a Full-On Obsession
The very first thing I did once I landed unexpectedly? I headed to Millennium Park. I took the standard selfie at The Bean (aka Cloud Gate), wandered by way of the gardens, and ended up listening to a string quartet play underneath the celebrities.
That was the second I knew this wasn’t simply one other metropolis.
A couple of issues I all the time advocate now:
🚤 Architecture River Cruise: The finest approach to see Chicago’s jaw-dropping skyline and be taught in regards to the metropolis’s wild architectural historical past.
🎡 Navy Pier: Ride the Centennial Wheel at sundown. The views of the lake and skyline are unreal.
🏙️ 360 CHICAGO or Skydeck at Willis Tower: Both supply panoramic views, however I’m a fan of 360 CHICAGO due to the lakefront views and the TILT journey should you’re feeling courageous.
Get Outside: Chicago’s Waterfront and Neighborhoods Shine in Summer
Chicago is aware of easy methods to do summer time proper. The Lakefront Trail is an 18-mile path alongside Lake Michigan, good for biking, strolling, or simply people-watching. You’ll cross seashores, parks, and skyline views that rival any coastal metropolis.
Some of my favourite neighborhood experiences:
🛶 Chicago Riverwalk – You can lease a kayak or simply seize a cocktail and watch the boats go by.
🎨 Pilsen – A colourful, mural-filled space with unimaginable Mexican meals and artwork galleries.
🍽️ West Loop – Packed with eating places and rooftop bars, it is a foodie dream.
Speaking of Food: Come Hungry (and Maybe Stretchy-Pants Ready)
No matter how lengthy your journey, meals must be a part of your itinerary. Start with the classics:
Want one thing extra elevated? Try rooftop eating at Cindy’s (insane Millennium Park views) or Aba within the West Loop.
And should you’re indecisive (like me), ebook a meals tour. They’re tremendous enjoyable and offer you a crash course within the metropolis’s meals scene.
We popped into Gino’s for a deep dish pizza and beloved it! Highly advocate in case you have the time.
This Is The Summer to Be in Chicago
Summer 2025 is about to be historic for Chicago tourism.
And whereas the stats are spectacular, the true magic is within the expertise: a spontaneous jazz efficiency within the park, a slice of caramelized crust pizza, a rooftop sundown that makes you are feeling such as you’re in a film.
So, whether or not you’re reserving a full journey or simply taking of venture on an extended layover, go!
Be a part of the power. Wander the neighborhoods, eat an excessive amount of pizza, and fall a little bit in love with the Windy City.
I do know I did.
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This article initially appeared on TravelOffPath.com
Opinions expressed listed below are the writer’s alone, not these of any financial institution, bank card issuer, lodge, airline, or different entity. This content material has not been reviewed, authorized or in any other case endorsed by any of the entities included throughout the publish.