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Top things to do in Chicago: 10 beautiful sights to see

"Oh, baby don't you wanna go? Back to that same old place - Sweet Home Chicago," sang the Blues Brothers in the classic film of the same name. The legendary blues song has even become Chicago's unofficial anthem. Chicago is the third largest city in the USA with the nickname "Windy City".

Thanks to a proud 77 neighborhoods, there is a huge cultural diversity in the metropolis on Lake Michigan: from Chinatown and Koreatown to large Mexican and Puerto Rican neighborhoods to German, Irish and Italian-influenced neighborhoods, you can really find everything here.

In this article, I'll show you the top 10 sights in Chicago. After that, there are some cultural tips and some important information about travel and accommodation. You can also look forward to the best photo spots and insider tips or secret places for eating and drinking in Chicago!

Created on17.09.2022
Die Reiseblogger Biggi Bauer und Florian Westermann

Overview of the top 10 sights in Chicago

What’s in Chicago to do? Here you can see a list of the top 10 sightseeing attractions to see in Chicago. I was there for six days with Anita, my co-blogger here at Phototravellers. In a week, the attractions are easily doable. If you only have a few days, it’s best to pick your favorite places and see how much time you have left at the end.

  1. Chicago River
  2. Millennium Park and Cloud Gate
  3. Buckingham Fountain
  4. Navy Pier
  5. Adler Planetarium, Shedd Aquarium & Field Museum of Natural History
  6. On the Lakefront Trail through Lincoln Park
  7. John Hancock Center
  8. Magnificent Mile
  9. Sears Tower
  10. Chinatown

Tip: To explore Chicago with all its beautiful sights for a reasonable price, we recommend the Go City Pass Chicago (order here*).

1. Chicago River

View of the Chicago River
View of the Chicago River from the Wells Street Bridge. Behind the yellow water cab, you can see the LaSalle Street Bridge with its bridge houses. At the bottom right you can also see a part of the Riverwalk, where you can walk to Lake Michigan. The river is one of the top things to do in Chicago

The first thing you’ll notice in Chicago is the Chicago River. The river is one of the very special places to visit and flows right through the city, giving the gray urban jungle a very special flair.

An exciting means of transportation that uses the Chicago River is the Water Taxi. A ride costs an average of $6, depending on the route, and a day pass costs only $10. You can pay by credit card directly on the boat. There are several routes and the stops are located along the river and on the shore of Lake Michigan. You can find more information about Water Taxi on their website.

Also, I can really recommend an Architecture River Cruise to anyone. The 75-minute boat ride teaches you all about the buildings on the left and right sides of the river. Our guide Victor told us that he’s been doing the job for 17 years, which really gave him a vast knowledge of the city’s history. Tickets for the Architecture River Cruise are available here, for example.

If you prefer to stay on land, you can walk along the river to Lake Michigan on the so-called Riverwalk.

View of the skyline on the Architecture River Cruise
The famous Architecture River Cruise gives you a unique perspective on the city and its attractions. Our guide Victor was awesome

The numerous bridges also offer great views of the Chicago River. Each bridge has its own charm, and the bridge houses are always different and exciting as well. From there, the bridge keeper – who actually used to live there – can open the bridge to passing ships and monitor who is passing. You’ll learn more about that on the Architecture River Cruise, too!

2. Millennium Park and Cloud Gate

A definite Chicago highlight that most will probably know about is the Bean. The “bean” is actually called Cloud Gate, which means cloud gate. The sculpture by British artist Anish Kapoor weighs nearly 100 tons and consists of 168 stainless steel panels. It took two years to build and was inaugurated in 2006. Since then, the landmark has become a classic photo motif in Chicago, on the one hand for distorted mirror selfies and on the other because the skyline is excellently reflected in the bean.

The Cloud Gate is one of the top things to do in Chicago
What to see in Chicago? One of the coolest things is the Cloud Gate. It’s also called Bean because of its bean-like shape

Where to visit it? Cloud Gate is located in Millennium Park, where you’ll also find an interactive fountain with video elements, a concert shell, and many other recreational opportunities. The park is open all day and – if no other events are taking place – free of charge.

Address: 201 E Randolph Street (Google Maps)

Selfie at Cloud Gate
What to do here? The highly polished surface of this landmark is ideal for self-portraits. Cloud Gate is one of the absolute top sights in Chicago
The Millennium Park in Chicago
Millennium Park also has several other tourist attractions to offer, such as beautifully landscaped green spaces and event venues

3. Buckingham Fountain

Millennium Park is an extension of the adjacent Grant Park. This large park is also known as Chicago’s front yard and is definitely worth a visit.

Probably the most famous attraction in Grant Park is the Buckingham Fountain. This fountain is modeled after one in the palace gardens of Versailles and is considered one of the largest fountains in the world, holding about 5.7 million liters of water. It is in operation from May to mid-October every day from 8 am to 11 pm. Every hour on the hour, starting at 9 a.m., there is a 20-minute water show that is extremely spectacular, especially after dark, thanks to the more than 800 lights. The last show starts at 10:35 pm.

Address: 301 S Columbus Drive (Google Maps)

The Buckingham Fountain in Grant Park at night
The Buckingham Fountain in Grant Park is a particularly impressive thing to do at night with the skyline in the background

⭐ Recommended travel guides for your trip to Chicago

We can recommend the following travel guides for your trip to the metropolis on Lake Michigan. One of the best guides you should check out is Fodor’s Chicago (Full-color Travel Guide) (get it here*). What you should also take is the Lonely Planet Chicago Guide (order now*).

4. Navy Pier

The biggest sight – and one of the most popular things to do in Chicago – is Navy Pier. The approximately one-kilometer-long pier was built in 1916 and first served as a storage and docking area for freighters. Even then, however, it was also the site of the first picnic areas and entertainment venues.

Pauline poses on the Navy Pier
Even at the end of September, you can still enjoy the sun in Chicago – the Navy Pier is perfect for this with a magnificent view

As part of the World’s Fair celebrated in Chicago in 1893, Navy Pier was the site of the world’s first modern Ferris wheel. Today you can still ride the Ferris wheel there, and a movie theater, a theater, a greenhouse with palm trees, and numerous other stores and attractions are also located at the famous Navy Pier. Many boat trips and also the water cab depart from here.

The Palm House at Navy Pier
The Palm House at Navy Pier is a sight in itself and the ideal place for a relaxed meeting

In the summer, Navy Pier is great for sunbathing and offers an impressive view of the skyline and Lake Michigan. There are even fireworks on Wednesdays and Saturdays. The pier is open all year round. The exact opening hours, which change depending on the season, can be found here on the website.

Address: 600 E Grand Avenue (Google Maps)

The Ferris wheel in Chicago is one of the top activities
The Ferris Wheel – one of the top attractions in the US metropolis – is of course no longer the original “Ferris Wheel” from 1893, but still enjoys great popularity

5. Eagle Planetarium, Shedd Aquarium & Field Museum of Natural History

You can take a water cab on Lake Michigan along the Chicago skyline directly from Navy Pier to the Museum Campus. The park has an area of 23 hectares and, like Millennium Park, is also part of the large Grant Park.

It’s home to three of the city’s most important museums and attractions: the Adler Planetarium, the Shedd Aquarium and the Field Museum of Natural History. Here you’ll learn all about astronomy, the underwater world, and natural history, in that order. Especially for the last of the three museums you should plan a lot of time, because a visit in one day is not considered sufficient.

On top of that, you have a breathtaking view of Chicago, the Navy Pier and Lake Michigan from the beautifully designed museum campus. This view alone is worth a visit!

Eagle Planetarium

View of the Chicago skyline with the Shedd Aquarium
Standing in front of the Eagle Planetarium, you’ll have this breathtaking view. On the far left, you can see the Shedd Aquarium in front of the Chicago skyline. It’s an amazing thing to do in Chicago!

Shedd Aquarium

Field Museum of Natural History

Address: 1400 S Lake Shore Drive (Google Maps)

Hours of operation: 9 a.m. to 5 p.m. daily. Last admission at 4 p.m.

 AdultsChildren (6-11 years) Students with ID and retirees 65 and older
All-Access Pass (all permanent exhibits, special exhibits and one 3D film)40 Dollar29 Dollar35 Dollar
Discovery Pass (all permanent exhibits and one special exhibit or 3D movie) 34 Dollar25 Dollar30 Dollar
Basic Ticket (all permanent exhibitions)26 Dollar19 Dollar23 Dollar
The Museum Campus with the Shedd Aquarium left and the Field Museum of Natural History
A part of the Museum Campus with the Shedd Aquarium on the left and the Field Museum of Natural History on the right

6. On the Lakefront Trail through Lincoln Park

One of my favorite discoveries in Chicago was the Lakefront Trail. We rented a bike near Navy Pier (address: 505 N Lake Shore Drive Google Maps) for $27 for the whole day. There are however innumerable providers. With it, we drove along the west shore of Lake Michigan.

The path, which is specially designed for cyclists and joggers, is just under 30 kilometers long. It’s super flat and easy to ride and offers beautiful views.

Biking the Lakefront Trail 
Cycling along the Lakefront Trail is an incredibly fun thing to do
Blick auf Chicago
After just a few minutes on the bike, you will have this view of Chicago- a stunning thing to see there!

One stop along the way that you must-do is North Avenue Beach. You could still get in the water there even at the end of September. And all this with the characteristic skyline in the background. A unique experience!

Address: 1600 N Lake Shore Drive (Google Maps)

Pauline in Lake Michigan
The water of Lake Michigan was still really pleasant at the end of September

Lincoln Park itself is also an extremely popular destination in Chicago. This means the park, through which almost the entire Lakefront Trail runs. With a length of over 11 kilometers, it is the largest public park in the city. There are numerous recreational activities, museums, and a zoo there.

7. John Hancock Center

Back downtown, it’s straight to the John Hancock Center– a really cool thing to do! After its completion in 1969, the skyscraper with a height of 344 meters was the second tallest building in the world after the Empire State Building in → New York City. In the meantime, however, it has been replaced by the Sears Tower, among others, but more on that later.

Floors 45 to 93 of the John Hancock Center contain living quarters that are accessible only to residents and their guests. One floor below, on the 44th floor, is the highest swimming pool in a building in all of North America.

On the 94th floor is the 360 Chicago observation deck. In good weather, you have a panoramic view of Chicago and Lake Michigan from here. A special highlight is TILT!, a moving platform that “tilts” up to 8 visitors at a 30-degree angle across Michigan Avenue. A bit of thrill and a terrific view – what more could you ask for?

By the way, you can recognize the John Hancock Center by its two distinctive antennas that stand out from afar.

Panoramic view from 360 Chicago
What’s to see in the John Hancock Centre? This outstanding panoramic view awaits you at 360 Chicago: once north…
Panoramic view from the 360 Chicago to the south
… and opposite in direction south… it’s definitely one of the best places in Chicago
A row of windows on the 94th floor of the John Hancock Center
This row of windows on the 94th floor can be tilted out of the John Hancock Center at a 30-degree angle. Do you dare to go onto the TILT?

8. Magnificent Mile

The John Hancock Center is located on what is known as the Magnificent Mile. This boulevard consists of the northern part of Michigan Avenue and is home to numerous luxury stores and stores.

Next to the John Hancock Center, for example, is the Water Tower Place shopping center, where you can find everything from souvenirs to clothes to snacks. My tip: try the original Chicago popcorn mix from Garrett. It consists of caramel and cheese popcorn – sounds crazy, but you should definitely try it!

The Water Tower Place shopping center is named after the Water Tower, which is located diagonally across the street. There is an exciting story about this attraction: In 1871, there was a devastating fire in Chicago that destroyed large parts of the city center. The Water Tower, which had been built only two years earlier, is one of the few buildings that survived the fire.

The tower, made of yellowish limestone, was originally intended to “inconspicuously” integrate Chicago’s drinking water pumping station into the cityscape. Inconspicuous is not exactly the tower in neo-Gothic style – but definitely an eye-catcher. Today, by the way, it houses a gallery and a visitor center.

The Water Tower in Chicago
The Water Tower is one of the oldest buildings in the city. It’s a must-do and one of the top things to do in Chicago

9. Sears Tower

The Sears Tower is the tallest building in Chicago, the second tallest in the US and the twentieth tallest in the world. It was actually renamed Willis Tower in 2009, but Chicagoans still call it Sears Tower, named after a local trading company that commissioned its construction. The skyscraper consists of nine square columns that give it stability. Thus, it reaches a total height of 442 meters, if you count the antennas, it is even 527 meters.

View from the Sears Tower at night
The view from the Sears Tower is also breathtaking – especially at night, definitely one of the best things to see in Chicago!

One of the most famous tourist attractions of Chicago is located in the Sears Tower. It’s the Skydeck on the 103rd floor. At almost 30 km/h, two of the fastest elevators in the world take you there in about 45 seconds. Incidentally, there is currently no building in North America other than the Willis Tower that still houses a floor at this height.

The observation floor includes the four distinctive glass boxes that protrude from the skyscraper and through which brave visitors can look down vertically. I would definitely recommend the Skydeck!

Keep in mind, however, that although you can get to the observation deck quickly, you usually have to wait in line for a long time in front of the glass boxes. When it’s your turn, you really only have a minute to take photos and can’t really enjoy the moment. Also, you must do vehemently resist having a picture taken with the “official” camera if you don’t want that. You could then buy the photos at the exit for a lot of money – rather let the staff take your picture with your own camera.

The Sears Tower in Chicago
The Sears Tower in Chicago – you can already make out the glass boxes at the top. The skyscraper is one of the most famous things to do in the city
Pauline and Anita in the glass boxes of "The Ledge"
The glass boxes (actually called “The Ledge”) on the Skydeck at 412 meters in height are not really a secret place but an absolute fun place to go in Chicago

10. Chinatown

So far, almost all of the sights have been in the so-called Loop, Chicago’s downtown district. Finally, we go a bit further south, to Chinatown.

In pretty much all major U.S. cities there is such a Chinese quarter. In Chicago, too, a visit is definitely recommended, as you can really immerse yourself in another world there for a short time. By the way, you can also take a water cab to Chinatown.

Chinatown in the south of Chicago
Chinatown in the south of Chicago. Pay attention to the details – even the roof in the upper left corner is inspired by Chinese architecture. It’s a really cool thing to do in Chicago

Other neighborhoods in Chicago are definitely worth seeing as well – after all, as I said, there are 77 of them. Little Village, for example, is also known as La Villita, an almost exclusively Mexican neighborhood. The north of Chicago, especially the area around Lincoln Park, on the other hand, is more Puerto Rican.

However, there are also neighborhoods like Englewood, Garfield Park, or Lawndale that you should definitely avoid. Chicago is considered one of the most dangerous cities in the U.S. due to its high gang crime rate, among other things.

For those interested in culture

You already know three of the most famous museums on Museum Campus. Not far away, on the western edge of Grant Park, there is another must-see for art lovers. The Art Institute was founded in 1866 and houses 300,000 works of art from five millennia.

On the other hand, you’ll find a great private art collection at the Nickerson House at 40 East Erie Street. It is also called the Richard H. Driehaus Museum and is located in a magnificent mansion near the Magnificent Mile. Also, very exciting sounds the International Museum of Surgical Science, which is located in the north of the city and offers an insight into the history of surgery.

Opera fans shouldn’t miss the Lyric Opera of Chicago at the Civic Opera House. With 3,563 seats, it’s the second largest opera house in the United States after the Metropolitan Opera in New York.

The Holy Name Cathedral
Holy Name Cathedral is a stop on the Crime & Gangster Tour. On one of the corners, you can still see alleged bullet holes from a shootout that killed a mobster in 1926

If you’re looking for a fun night out, the well-known Second City Comedy Club is the place to go. If jazz is more your thing, pay a visit to the Green Mill in the Uptown neighborhood. The bar is considered one of the oldest jazz clubs in the U.S. and the longest continuously operating nightclub in Chicago. By the way, the famous Mafioso Al Capone was the unofficial owner of the Green Mill.

Speaking of the Mafia, the so-called Chicago Outfit is an offshoot of the Sicilian Cosa Nostra, known as the “Mafia”. There is a super exciting Free Walking Tour to go along with it, which means there is no set price and you end up giving as much as you want. Our guide Matt even knew a bit of German and in two hours he took us to important places related to organized crime in Chicago and told us exciting stories about them. You can reserve a spot for the Chicago Crime & Gangster Tour here.

One last tip that we, unfortunately, didn’t make it to ourselves is the Garfield Park Conservatory. This is one of the largest greenhouses in the US and a true paradise for plant lovers. The entrance is free.

Extra tip for series fans

The Engine 18 Firehouse in Chicago
The Engine 18 firehouse becomes Firehouse 51 in the television show Chicago Fire- it’s a cool place to see!

If you’re a fan of Dick Wolf’s Chicago series like Anita and I are, you can’t miss two things. One is the firehouse where Chicago Fire is filmed.

Firehouse 51 is actually called Engine 18 and is located at 1360 S Blue Island Avenue (Google Maps). This is a real firehouse, with actual firemen and women working there. You should keep that in mind when you go there. It is possible though – the people there are super nice and are happy to give tours of the building and tell you about their experiences with the actors.

Selfie in front of a fire truck
I’m sure the firemen and women who work there will be happy to show you around and take some great souvenir photos

Plus, you can buy a firehouse t-shirt for $20. Look for notices on trees and streetlights in the neighborhood to find out when filming is taking place on site. You may be able to catch a glimpse of the shoot, but please be respectful and follow the instructions of the staff.

Post with the date of filming
These are the notes in the neighborhood that tell you when the crew will be on location
Shooting with a fire truck
This is what it looks like when filming takes place

You can also visit the police station from Chicago P.D., Chicago Fire’s spin-off about the city’s cops. It’s not particularly exciting inside, but you’ll definitely recognize the building during outdoor scenes. In addition, the Maxwell Street Station, which houses the 21st Precinct in the series, is just a few minutes walk from the fire station – at 943 W Maxwell Street (Google Maps).

This is where the exterior scenes of the Chicago P.D. police station are filmed 
This is where the exterior scenes of the Chicago P.D. police station are filmed. To see this is a really cool and unusual thing to do in Chicago!

Chicago Explorer Pass

We can definitely recommend the Chicago Explorer Pass for just under 75 Euros. With it, you can visit 3 attractions. The option with 4 attractions costs almost 100 Euro, the option with 5 costs about 111 Euro. You can choose the attractions you want to visit.

There are for example the Skydeck and 360 Chicago, the Adler Planetarium, the Art Institute, the Architecture River Cruise, and many more. Another bonus: at some attractions, you can use the “Fast Lane” and don’t have to wait in line as long. You can get the Chicago Explorer Pass here*.

⭐ Where to stay in Chicago – the best hotel tips

If you want to stay centrally, you have to budget a little more money. But then, in return, there are also fantastic accommodations. For example, the 4-star The Silversmith Hotel (check rates here*), which is located right next to Millennium Park. The 4-star Virgin Hotels Chicago (check rates here*) is also very centrally located and also has its own rooftop bar and nightclub. A cheaper option is the 3-star HI Chicago Hostel (check rates here*), which is also close to Buckingham Fountain.

Another great option is vacation rentals. For example, there’s Kasa Chicago (check prices here*) in the South Loop, a modernly designed apartment with super connections to downtown. The Wicker Park Apartment (check rates here*) in the Northwest is also great and is close to the Division Station on the Blue Line, which goes to downtown and the Chicago Airport.

Getting there and transportation

Inside the Chicago Elevated
A typical train of the L, as the Chicago elevated is called
View from the Chicago Elevated
From the L you have a great perspective on the city

O’Hare International Airport is a major hub in the United States. Here you’ll find out the best way to get to the city from Chicago Airport.

If you’re traveling from elsewhere in the U.S., you may arrive by train or bus. The most used train station is Union Station, which is located near the Willis Tower and is also architecturally impressive.

Probably the most famous bus terminal belongs to Greyhound and is not far from Union Station. I was warned before our trip that in the U.S., except for other European travelers, only long-distance buses are used by those who cannot afford their own car or want to avoid the strict airport controls. The Greyhound terminal was indeed not very inviting, but we had no problems there.

There are also numerous transportation options in the city itself. The Ventra Card is a reloadable card from the CTA, the Chicago Transit Authority. With it, you can use all means of transportation of the CTA, like the L. You can easily get the card from the machine at the elevated train stations, and then you can reload either daily passes or specific amounts of money.

You already know our favorite means of transportation: the water cab. Of course, you are very limited and can only move along the river. However, you can cover long distances relatively quickly.

In downtown Chicago, you can also get around on foot and reach most of the sights. You can also overdo it – like Anita and me: on one day we covered almost a half marathon with almost 21 kilometers and covered the Riverwalk, Millennium Park, Navy Pier, the Skydeck, and some photo spots within 14 hours. In between, we even had time for the Architecture River Cruise.

If that’s a bit too much for you, you should definitely download the Uber app. It’s a fast, reliable, and cheap way to get around. We mainly used this option when we had to get a little further away from the center – for example, to the fire station – or the way home at the end of the day was just too far for us.

Events and sports

One of the most famous events in Chicago is Saint Patrick’s Day. Because of the many Irish immigrants who came to Chicago since the 19th century, it is celebrated especially big. The highlight: The entire Chicago River is dyed green.

There are also numerous other events, such as a blues and a jazz festival or the Taste of Chicago as the largest food festival in the world. The Air & Water Show is an annual air show in August, consisting of performances by the world’s best military and civilian pilots on the shores of Lake Michigan. There is even a “Christkindlmarket” in Chicago, which may be due to the high number of German immigrants.

Sports fans also will enjoy Chicago to the fullest. American football is represented by the Chicago Bears, ice hockey by the Blackhawks, basketball by the Bulls and the Wolves, and baseball by two Major League teams, the White Sox and the Cubs. The latter team’s ballpark, Wrigley Field, is said to be especially worth a visit. The Chicago Fire soccer team – not to be confused with the TV series – should also be familiar to many: Bastian Schweinsteiger played here until 2019.

Facts and figures about Chicago

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