Subscribe to my Newsletter
Get the latest travel inspiration straight to your inbox!
By submitting you agree to your data being stored for newsletter purposes. Read more.
The 20 Best Things to Do in Chicago
Chicago impressed me the first time I saw it. Here you will find all tips for the Windy City.
Aktualisiert: 07/08/2025
Chicago is a truly impressive city: a huge skyline, pure city life, but also lots of greenery and long beaches on the shores of the huge Lake Michigan. Unlike its big sister New York, the people here are incredibly open-minded and friendly:
Sightseeing in Chicago: My budget tip!
Chicago is not exactly cheap! As in all major American cities, accommodation and meals are a big hole in the wallet. But you shouldn’t skimp on good food in the foodie mecca of Chicago! And you shouldn’t miss out on some of the paid attractions such as the Willis Tower (or 360 Chicago) or the Art Institute.
My tips:
➜ Save money on many sights: Buy a Chicago Pass in advance!*
➜ Compare prices & book your accommodation in good time here!*
#1 The Bean & Millenium Park
Sir Anish Kapoor’s sculpture in Millennium Park is actually called Cloud Gate, but because it looks like a bean, the nickname stuck: The Bean. This is probably the most popular must-see photo spot in the whole of Chicago. Not only because of the crowds of people who make a pilgrimage here every day, but also because of The Bean itself: The reflections in the stainless steel sculpture are simply fascinating.
But The Bean is not the only work of art worth seeing here: next door is the Crown Fountain, a water-spouting video installation that provides refreshment, especially for children, during Chicago’s scorching hot summers.
Welcome to my travel blog
Hey, I’m Tatiana and I’m the blogger behind The Happy Jetlagger. Since 2014, I’ve been sharing my personal travel stories on this blog. I don’t have a big team behind me, so I’m pretty much a one-person show: I’ve researched and tested all recommendations myself.
#2 Willis Tower
The Willis Tower used to be called the Sears Tower and was the tallest building in the world. That is ancient history, but the view from Skydeck Chicago is still impressive. The four glass balconies (“The Ledge”) are a particular highlight: Even the floor is made of glass. Not for those afraid of heights.
➜ Save yourself waiting time & buy your ticket here in advance*
Do you also want to travel to the USA?
There are lots of helpful tips and travel reports on my USA blog.
#3 360 Chicago at the John Hancock Center
If you want to see Chicago from a different perspective than from the Willis Tower, you should go to 360 Chicago. On the Tilt extra attraction, you can lie down on glass panes that tilt forwards.
By the way: admission to attractions such as the Skydeck or 360 Chicago is quite expensive. With the Chicago City Pass* you can save up to 50%, so it’s best to work out in advance whether you want to pay for admission individually or whether you’d rather take the pass.
#4 Magnificent Mile / Michigan Avenue
Michigan Avenue in the center of Chicago is lined with one huge store after another: All the big stores are represented here. Quite ostentatious – which is why this stretch of Michigan Avenue is also known as the “Magnificent Mile”.
Incidentally, you can stay here in style at the Warwick Allerton, one of Chicago’s most historic hotels. Recently renovated, you live here in one of those old skyscrapers like in the movies: large rooms, high ceilings. And everything at its finest.
Ad / *affiliate links
+++ Exclusive +++
Get 5% off on any GetYourGuide tour
Code: THEHAPPYJETLAGGER5
#5 Chicago Riverwalk
The formerly derelict banks of the Chicago River have been given a real facelift: now you can stroll along them or simply take a short lunch break at one of the beach bars. The more sporty get into a kayak, the more comfortable take one of the water cabs and explore Chicago by water. By the way, water cabs are part of Chicago’s public transportation system!
➜ Timetables & tickets for the water cabs can be found here!
#6 Navy Pier
The leisure area directly on the lake is almost in the middle of the city. Almost a hundred years old, it was given quite a facelift in the nineties and now offers all kinds of leisure activities, from a Ferris wheel to a musical theater and art exhibitions.
You have a great view of Chicago and Lake Michigan from the Ferris wheel:
➜ Buy your ticket for the “Centennial Wheel” on Navy Pier* here
The numerous cafés and restaurants are a great place to take a break from sightseeing and enjoy the view of Lake Michigan – in the beer garden, for example, with a beer and a traditional Chicago hot dog. There are always free fireworks on Wednesday and Saturday evenings. Many other free events such as concerts and festivals can also be found in the event calendar.
#7 Chicago Elevated, Loop, “L”
It is actually called Chicago Elevated, but Chicago’s elevated train is also known simply by the letter “L”. Particularly striking is the Loop, the ring that cuts through the street canyons in the middle of Downtown.
#8 Lake Michigan and Lakefront Trail by Segway
The Lakefront Trail runs along the entire length of the city, perfect for jogging, cycling – and Segway riding! The distances are huge, so a vehicle is pretty handy.
With a Segway you can see a lot more of Chicago’s long waterfront promenade. The lakefront is definitely one of Chicago’s great leisure attractions: An absolute must when the weather is nice!
Ad / *affiliate links
#9 Art Institute of Chicago
If you really want to see all the exhibitions, you’re guaranteed to be busy for a whole day. But a visit just for the highlights is also worthwhile!
Numerous American classics such as Edward Hopper’s Nighthawks hang in the Art Institute of Chicago .
Admission is quite steep at 25 dollars, but with city passes such as the Chicago City Pass* you can save a lot of money here too if you are sightseeing through Chicago anyway.
You can read my experience report about the Chicago City Pass here: Chicago City Pass – Is it really worth it?
#10 Chicago Theatre
Even if you don’t attend a show at the Chicago Theatre, a photo in front of the legendary neon sign is a must! At lunchtime, you can take a guided tour of the inside of the venerable Chicago Theatre, and in the evening, superstars from Jerry Seinfeld to Madonna perform here. Or you can visit the Chicago Theatre during the day with a guided tour*.
#11 Jazz clubs & live music
Jazz and blues are the leading musical genres in Chicago. And if you don’t feel like dancing after a long day of sightseeing, a jazz club is the perfect choice to round off a day in Chicago. Andy’s Jazz Club, for example, offers live music from all jazz genres every evening with good cocktails.
#12 Chicago’s Deep Pan Pizza
Chicago is famous for its deep dish pizza or deep pan pizza, which was invented here in the 1940s. The original is said to have originated at Pizzeria Uno – but Gino’s East and Lou Malnati’s can also look back on a long deep pan pizza tradition. Unlike traditional pizza, Chicago pizza is served in a pan, with the cheese underneath the other toppings on a cornmeal crust. It may not have much to do with an original Italian pizza, but the Chicago pizza is still delicious.
Gino’s East is worth a visit for the interior design alone: the entire(!) restaurant is scribbled on from top to bottom. Every guest can immortalize themselves here with a sharpie!
#13 Route 66
The legendary Route 66 actually starts here in Chicago! Route 66 is no longer an official road, but the old sign on Adams Boulevard marking the beginning is still there. By the way: A road trip along Route 66 from Chicago, as I did, is also highly recommended! You can read more about my road trip through Illinois here:
#14 West Loop, Randolph Street & Fulton Market Street
The new restaurant mile in Chicago’s gastronomic heaven: Chicago is known for its fantastic restaurants. In West Loop, a new generation of eateries has established itself along Randolph Street and Fulton Market. There’s always something going on here in the evening.
Once a year, in summer, there is the“Taste of Randolph“, a street festival with events and live music, in which many of the neighborhood’s restaurants participate and where you can try all the specialties for a small price.
My tip: breakfast at Soho House!
#15 Wicker Park
In Berlin you would say: Wicker Park is really cool. In big cities, I always like to take a look at the small, neighborhoods because you simply get to see more of real life here. If I hadn’t opted for accommodation in the middle of the city, I would probably have ended up in Wicker Park, one of Chicago’s hipster neighborhoods, so to speak. Street art, cool bars, individual stores – my creative heart was happy!
My tips for Wicker Park:
Dove’s Luncheonette Really, really cool location: Tex-Mex cuisine is reinterpreted here in retro luncheonette style under the elevated railway bridge. Could have tasted my way through the entire menu.
Milwaukee Avenue If the Magnificent Mile is too busy with huge chain stores, you’ll feel much more at home shopping on Milwaukee Avenue. Here you can still find small stores between larger indie chains like Urban Outfitters, and you can stroll around much more comfortably than on the sometimes hectic Mag Mile.
#16 The 606 / Bloomingdale Trail and Park
Relatively unknown, as it is located just outside the city center between Logan Square and Humboldt Park: The 606 is a disused elevated railway line that has now been converted into an amusement park. Above the rooftops of Chicago, you can jog, cycle and do whatever else you can think of over a length of more than 4 kilometers. A great detour when visiting Wicker Park!
#17 Humboldt Park
A melting pot of cultures – that’s always a hackneyed phrase when talking about life in big cities. In Chicago, however, it really hits the nail on the head. People from so many nations live here that you sometimes feel like you’re on a little trip around the world. Humboldt Park is a district where many Puerto Ricans live: In summer, there is a big street carnival here with lots of salsa, bachata, reggaeton and merengue and my Brazilian genes were jumping in triangles!
#18 Buckingham Fountain
Children of the 90s will immediately recognize it and revel in TV memories: When I saw the Buckingham Fountain in Grant Park, I immediately thought of the opening credits of “A terribly nice family”. The best thing for everyone else to do is simply marvel at one of the largest fountains in the world. The Buckingham Fountain is really huge!
#19 Oak Street Beach & Co.
Chicago simply has it all: vibrant city life, lots of greenery, the great Lake Michigan – and even great city beaches! Oak Street Beach is one of the most popular, but you wouldn’t expect to find beaches like 12th Street Beach next to the Adler Planetarium in a big city like Chicago.
#20 Chicago for gourmets and foodies
Chicago lives up to its name as a gourmet destination. Food is generally a tricky subject in the USA – while you can find burgers and deep-fried convenience products on every corner, other dishes can sometimes be a bit hit and miss. In Chicago, however, everyone should be able to find what they are looking for.
You can find more restaurant tips for Chicago in my Chicago restaurant guide!
***
More articles about Chicago
- Chicago Food Guide: 6 Really Good Locations
- The 20 Best Things to Do in Chicago
- Chicago CityPASS: Experience, comparison & prices
*Transparency note: One of my stays in Chicago was partly at the invitation of Enjoy Illinois.
Das könnte dich auch interessieren
