Best Things to Do in Chicago in Summer

Aktualisiert am: 10/03/2024

Want to go to Chicago this summer? City breaks in the US actually go all year round, but here in this article I’ve put together a few summer ideas for you specifically! And don’t worry, Chicago is really exciting in the summer too!

The 20 best sights in Chicago
My food guide for Chicago
Architecture in Chicago
Cheap hotels in Chicago*

Chicago in summer view of Chicago River and skyline

When I said goodbye to Chicago for the last time, I actually became very sentimental: only 24 hours had been enough to let this city fascinate me. Maybe also because I ended up there without great expectations.

Welcome to my travel blog!

Hey, I’m Tatiana, a German-Brazilian living in Berlin & the author behind The Happy Jetlagger. I’ve been writing about my travels since 2014. In addition to my job as a flight attendant, this blog is my passion project!

Chicago: The insider’s tip among major American cities

Who already has Chicago on their radar as a cool city? During this time, when I exceptionally flew long haul instead of short haul, I was often in the USA. That never really gladly: the flights were anyway strenuous, the rest time short and if one already stands as actual Berlin long sleepers unusually already at four o’clock in the morning jetlagbedingt vertically in the hotel bed, then the following half free day takes already no good beginning.

Chicago in summer passing elevated train Chicago Loop

And in general, there wasn’t much that attracted me to the destinations in the USA: Sure – it was great to get to know Boston, Washington or Denver, not to mention New York (which I already knew, but you can never get enough of New York) and Miami. But New York is New York, and Miami – well, with my South American roots, that was more like a visit home than the great America.

Read all articles on Chicago and Illinois

Chicago Theatre by night city trip to USA

Only Chicago had grabbed me by the end of my long-distance visit, and somehow quite unexpectedly. On my personal must-see map, Chicago never existed – but then it turned out to be such a great city that I didn’t want to leave: Great architecture, a skyline and big city flair almost like New York, great museums, huge shopping temples and still a friendly, almost warm atmosphere everywhere you go. The grouchy Berliner in me was irritated and thrilled at the same time. As expected, it was hard to say goodbye. I would have liked to stay 1-2 days longer, but no one asks me when I’m on duty. The pick-up is waiting, go, go, off to the airport, back to Germany. And I knew: This was definitely not the last time I was here. As luck would have it, I ended up back in Chicago almost a year later – and this time I didn’t have to go back after 24 hours. One thing in advance: My enthusiasm for the city has not changed.

Chicago as a summer destination: city trip to the USA

Chicago can get freezing cold and more than uncomfortable in the winter – summer is all the more beautiful for it. Basically, you have to be prepared for all kinds of weather in Chicago. Within a few days, the weather changed from windy and rainy to the worst heat wave with an official weather warning. But the constant extreme weather changes didn’t seem to rob anyone of their good mood, and more than once I heard the standard general saying about the weather:

If you wish for different weather in Chicago, just switch sides of the street!

And that’s how everyone enjoys summer in Chicago: with free concerts and events everywhere, street festivals, beach life (yes, there are little stretches of beach on Lake Michigan almost in the middle of the city, too) or just barbecuing in the front yard.

Buckingham Fountain in Chicago city trip USA

What is there to do in Chicago in the summer? Some tips.

The list of sights and “things to do” in Chicago is long. Especially in the summer, there are many more outdoor options, so these are just a few suggestions for making the most of your stay in Chicago.

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Millenium Park – Concerts for free and a photo in front of “The Bean

The Bean is actually called Cloud Gate and is a sculpture by Sir Anish Kapoor. The Bean quickly became the city’s landmark after its completion in 2006, and today crowds of tourists scramble in front of it every day to get the best photo together with The Bean. Me too, of course, because The Bean impressed me last time I was in Chicago. The reflections of people, skyline and sky on the brightly polished surface are simply fascinating.

Chicago city trip USA in summer The Bean

Next door, at the Jay Pritzker Pavilion, an open-air venue, and the adjacent parks, there are free(!) concerts and music festivals throughout the summer, from jazz to house to reggae, plus all sorts of events like morning yoga or urban gardening projects. It’s worth taking a look at Millennium Park’s annual summer program!

Street parties without end: Get out into the neighborhoods of Chicago!

It’s not just the middle of the city that’s celebrating summer; outdoor events are always happening in Chicago’s individual neighborhoods and wards. Chicago is truly a melting pot of many different cultures and each one celebrates itself with its own event, or so one gets the impression. What I found remarkable was that many immigrant families in Chicago have lived in Chicago for several generations and still maintain their own culture – without isolating themselves. They’re all Chicagoans at heart, too – and you can feel that commonality. The atmosphere in Chicago is also truly unique in terms of multicultural coexistence.

Humboldt Park neighborhood in Chicago

In Humboldt Park, for example, the Puerto Rican Festival took place – parades, car parades, a park full of fairground booths and salsa and reggaeton on every corner. Inviting and open to all.

Puerto Rican Festival in Humboldt Park in Chicago USA

Or there are food festivals like theTaste of Randolph in West Loop. This district used to be an industrial area with warehouses and factories, but in recent years it has mutated into an absolute food mecca (Chicagoans love good food so much) and hipster district.


Around Fulton Market and along Randolph Street, there are the most amazing restaurants and bars; so many that you would definitely need a few weeks to try your way through them. The Taste of Randolph is therefore the best opportunity. All of these restaurants have a food stand and offer their best dishes for a small price. In addition, there are stages with really good music – and once again: an absolutely inviting and relaxed atmosphere. They’re just hearty, these Chicagoans.


With the Segway through the parks of Chicago

When you see all the skyline photos of Chicago, it seems incredible that there are large green spaces in the middle of this city. But just as with Central Park in New York, Chicago has made a point of maintaining large parks in the middle of the city, such as Grant Park, which houses Millennium Park, or Lincoln Park with its free (!) zoo.


I explored Grant Park and the following green areas along the shore of Lake Michigan by Segway – which in retrospect was really a good idea despite the high temperatures. On the one hand, the airstream cools a bit, and on the other hand, the whole facility is so huge that it would take a long time to walk around. In addition, the entire route is relatively flat and well paved. Segway riding is learned within minutes and is a lot of fun!

Book the Segway tour along Lake Michigan*

Chicago from above – the two best options

A city like Chicago is best viewed from above – there are two special spots for that: the Willis Tower (formerly Sears Tower and once the tallest building in the world) or the 360 Chicago Observation Deck on the John Hancock Tower in the middle of Michigan Avenue, the main shopping street Magnificent Mile. Both offer great views of all of Chicago and Lake Michigan when the weather is good – and both locations have an extra gimmick! On the Willis Tower skydeck, there are four fully glazed exits, and in 360 Chicago, you can recline on angled panoramic windows that tilt forward.


Coming early is worth it, the view is better and you save long queues, especially in summer. The sunset from one of the viewing platforms is also worth seeing. Unfortunately, the entrance fee is quite steep, but with a Chicago City Pass you can save money. The best thing you can do is just compare: Is the Chicago City Pass worth it? (Experience & Prices)


Want to read more about Chicago? Here are all the articles:

The 606 – outdoor secret in Wicker Park

The neighborhoods in Chicago are definitely worth exploring. Areas like Wicker Park, Bucktown, Logan Square or Boystown all have their own charm and you can easily spend a whole day taking a closer look at individual neighborhoods. Wicker Park, for example, has lots of great cafes and restaurants where you can sit outside in summer temperatures (always works for me as avoid air conditioning). And cute stores. And in between street art. The perfect environment for a chill day in Chicago!


If you’re still in the mood for the outdoors after the downtown parks, check out the 606 Trail in Wicker Park – a relatively well-hidden old elevated train track that’s been converted into a recreation area similar to the Highline in New York. The entrances are hard to find right away and tourists are less attracted to it, but once you’re up there, you get to see Chicago’s residential areas from a different perspective. Nice contrast to the busy center! How to get there: 606 Trail website.


Around Chicago by boat, bus and train – Public transportation makes it easy!

Because it was so nice last time, and to remember this great day again, I took a boat trip again this time. The possibility to almost drive through the skyscrapers is unique.


The architecture boat tour* is really very good and stands out very much from usual tourist tours. The guides really have a broad knowledge of architecture – and I would never have guessed before my first visit that Chicago was so interesting architecturally! For those who are not so interested in architecture after all, I recommend at least a classic boat tour through Chicago to see Chicago from Lake Michigan at least once – the view of the skyline from the water is unique. To get around the city, you can simply take one of the water cabs. They’re smaller, usually never crowded, and with a day pass for just $10, you can explore the city like a hop-on hop-off bus! In fact, the Water Taxis stop at all major points along the Chicago River. Coupled with a CTA day pass, also only $10, which allows you to use all public buses, subways and elevated trains (including the one that goes all around the center, The Loop, and has great views!), it’s the perfect combination.

Book the architecture boat tour on the Chicago River here*

Book the classic boat tour through Chicago and onto Lake Michigan*

Chicago accommodations

A hotel or a place to stay is no problem in a city like Chicago – just unfortunately very expensive. But what is also really worth it with this fantastic city.

Here are a few self-tested hotel suggestions:

Low budget with authentic charm: Freehand Chicago*, right in the middle and equipped with a sensationally good bar not only for hotel guests
Huge hotel classic with impressive ballroom as entrance hall: Hilton Chicago* on Michigan Avenue
Right on the Magnificent Mile: the Warwick Allerton Chicago* combines big-city flair with classic luxury

Disclaimer: I was invited on this trip by Enjoy Illinois . Of course, my opinion remains unaffected – I was already enthusiastic about Chicago before anyway :)

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