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I was not going to fall in love with Chicago. My flight was canceled and I ended with an unexpected overnight stay.
But instead of sulking in an airport hotel, I ventured into town, and wow that was the right call! A quick walk turned into a spontaneous adventure: view of the skyline from the riverwalk, live music drove through Millennium Park, deep Schotelpizza that changed my life. I wondered and wondered why I had not booked a real journey there in the first place.
Now Chicago will break tourism records of all time this summer and it makes perfect sense. If you think of an escape from the city that combines great energy with Chill Lake Vibes, this is it.
This is why you should experience Chicago in the summer of 2025:
Record flights, easy access: it has never been easier to get there
The accessibility of Chicago this year is outside the charts. Both O’hare And Midway International Airport make up for their busiest summer ever, with almost 17.8 million Departure places expected between June and August, according to the Chicago Department of Aviation.
That means more options, better prices and new routes, including exciting additions such as Madrid, Naples and even Reykjavik.
Large airlines such as American” UnitedAnd Southwest Are all in expansion mode, so it’s a piece of cake in Chicago to go to Chicago. If you fly in the house, you will be spoiled as a choice. If you fly internationally, you will probably find direct connections that you have not had before.
Pro -tip: once you have landed, skip the expensive ride share and jump on the CTA ‘L’ TrainO’Hare connects via the blue line and halfway through the orange line. It is cheap, fast and lets you fall directly to the center.
Festivals, Food and Fireworks: The Summer Calendar of Chicago is Wild
There is something in Chicago with the summer. The city turns into one gigantic outdoor festival, with events almost every weekend and free concerts in the park, so you have forgotten that you are in the middle of a large metropolis.
Here are only a few events on my radar before 2025:
- 🎸 Lollapalooza (31 July – 3 Aug): Olivia Rodrigo, twice, Korn and Tyler, the maker are all headline this year. Enough said.
- 🎷 Chicago Blues Festival (5-8 June): a free, multi-phase celebration of the legendary blues finishing of the city.
- ✈️ Air & Water Show (16–17 August): Fighters and stunt aircraft rise over Lake Michigan, and it is completely free.
- 🏁 Nascar Chicago Street Race (5-6 July): Racing through the streets in the city center? Only in Chicago.
You can also catch smaller neighborhood feelings such as Andersonville’s midsommarfest or Wicker Park FestWhere you will find great food, local bands and that sober Chicago Community atmosphere.
My spontaneous visit turned into a complete obsession
The first thing I did when I landed unexpectedly? I went to Millennium Park. I took the usual selfie at the Bean (aka cloud gate), walked through the gardens and finally listened to a string quartet game under the stars.
That was the moment that I knew this wasn’t just a city.
A few things that I always recommend:
- 🚤 Architecture River Cruise: The best way to see and learn the stunning skyline of Chicago about the wild architectural history of the city.
- 🎡 Marine pier: Drive the hundred -year -old wheel at sunset. The view of the lake and the skyline are unreal.
- 🏙️ 360 Chicago or SkyDeck at Willis Tower: Both offer a panoramic view, but I am partly for 360 Chicago because of the view of the lake and the tilt ride if you feel brave.
Go outside: Chicago’s waterfront and neighborhoods shine in the summer
Chicago knows how to do the summer well. The LakeFront trail is an 18-mile path along Lake Michigan, perfect for cycling, walking or just watching people. You pass beaches, parks and skyline views that compete every coastal city.
Some of my favorite neighbor experiences:
- 🛶 Chicago riverwalk – You can rent a kayak or just grab a cocktail and see the boats pass by.
- 🎨 Pilsen -A colorful, with wall painting filled with incredible Mexican food and art galleries.
- 🍽️ West -loop – Packed with restaurants and bars on the roof, it is a foodie dream.
Speaking of food: come hungry (and maybe stretchable pants ready)
No matter how long your journey is, food must be part of your travel schedule. Start with the classics:
Do you want a little more increased? Try to dine the roof at Cindy’s (Insane millennium park view) or ABA In the West Loop.
And if you are indecisive (like me), book one Food tour. They are super fun and give you a crash course in the food scene of the city.
This is The Summer to be in Chicago
Summer 2025 will be historical for the tourism of Chicago.
And although the statistics are impressive, the real magic in experience is: spontaneous jazz performance in the park, a piece of caramelized crust pizza, a sunset on the roof that gives you the feeling that you are in a movie.
So whether you book a full journey or just take a gamble on a long stopover, go!
Part of the energy. Walk through the neighborhoods, eat too much pizza and falls in love with the windy city.
I know I did that.
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This article originally appeared on Traveloffpath.com
Opinions here are only the author, not those of a bank, credit card emitting, hotel, airline or other entity. This content has not been assessed, approved or otherwise approved by one of the entities that are included in the post.
