Looking for the best things to do in Chicago? Then you have come to the right place. In this blog, I will share with you a complete list of the 50 best things that you can do in Chicago. Planning your itinerary for a trip has never been this easy, All you will have to do is choose the ones that you the best and start having some fun!
Plan Your Trip To Chicago
- Book your flights with Skyscanner.com
- Find the best places to stay on Booking.com
- Find the best activities and tours, like this Architecture River Cruise
- Get reliable travel insurance.
- Don’t forget to pack a power bank and universal adaptor.
- Save some money with the Chicago City Pass.
Things To Do Around Grant Park and Museum Campus
1. Visit Millenium Park and The Bean
Cloud Gate or The Bean as it is most popularly known is probably one of the most famous landmarks of Chicago. Located within Millenium Park, it is a public sculpture by the artist Anish Kapoor. It is made out of 168 stainless steel plates welded together and polished. It is supposed to be inspired by liquid mercury.
The sculpture reflects people and the city skyline, so it is a very photogenic place. You will not be able to stop taking videos and photos of it.
Good to know: The sculpture gets quite busy so arriving early in the morning is recommended. We were there at around 9 – 10 am and even though it was already quite busy, we managed to get some photos with not so many people around us.
3. Enjoy the images and water display at Crown Fountain
Also located within Millenium Park, Crown Fountain is not just a regular fountain. It is also a piece of art by the Spanish artist Jaume Plensa.
The fountain consists of two glass block towers, on each side of a shallow reflecting pool, that project images of the faces of people from Chicago from a wide social spectrum. It is an analogy to the gargoyles that were carved in fountains in the past to have water come out of their mouths.
The face images are visible all year round. However, the water features only work between mid-spring to mid-autumn.
The fountain is located 100 m away from The Bean, but there were hardly any people there.
3. Enjoy a free open-air concert at the Jay Pritzker Pavilion
Jay Pritzker Pavilion is an open-air concert hall designed by the architect Frank Gehry. During the summer months, it is quite frequent attend to concerts and shows in the park.
The construction of this pavilion had a lot of controversies as there are historical height limitations on the buildings within Grant Park. To avoid these, the concert pavilion is considered an art piece rather than a building.
4. Cross the Serpentine-like BP Pedestrian Bridge
Right next to the Pritzker Pavilion, you will find the BP Pedestrian Bridge also designed by Gehry. It is a snakelike bridge that connects Millenium Park with Maggie Daley Park. The bridge is named after the energy company after it donated 5 million dollars for its construction.
While crossing this bridge, make sure to turn around and enjoy the beautiful glimpse of the Chicago Skyline.
5. Get impressed by Buckingham Fountain
The Clarence F. Buckingham Memorial Fountain, right in the center of Grant Park, is one of the largest fountains in the world and it was designed to imitate one of the fountains of Versailles Palace.
Good go to know: The fountain only operates between mid-May and October and offers water shows every hour. In the evenings these are with colored lights so make sure to plan your visit so that you arrive in time to enjoy the show.
6. Walk in between a sea of legs of the Agora Sculpture
Agora sculpture is located in the southwest corner of Grant Park. It is an art piece that consists of 106 headless and armless iron sculptures and it was designed by the Polish artist Magdalena Abakanowicz.
When installed, this sculpture produced mixed feelings among the citizens of Chicago. Many of them loved it and many hated it.
In my opinion, I really liked this art piece. It was a lot of fun to walk around the different sets of legs. It felt like you were walking through a small maze of legs.
7. Visit one of the statue of Abraham Lincoln, Head of State
Also in Grant Park, you can visit the statue of Abraham Lincoln, Head of State. This is a bronze statue of Abraham Lincoln by the artist Augustus Saint Gaudens. With this piece, the artist wanted to evoke the loneliness and burden of command Lincoln felt during the Presidency.
There is a second statue of Lincoln by the same artist in Lincoln Park.
8. Visit Sue, the T-Rex, at Field Museum
The Field Museum of Natural History in Chicago (FMNH) is one of the largest science and natural history museums in the world. Here you will be able to admire the skeleton of Sue, the most complete T-Rex skeleton that is conserved today. Sue is 12,3m long and 4m high. It was named after the person who discovered Sue Hendrickson and people usually refer to it as a female. However, the actual sex of this T-Rex is not known.
9. Discover Adler Planetarium
Another museum you should consider visiting is the Adler Planetarium. It is an astronomy and astrophysics museum that is located near the Field Museum within the Museum Campus.
Adler planetarium was founded in 1930 and was named after its founder, Max Adler. It was the first planetarium to open in the United States. It is also a research center for planetary geology, star formation, gamma-rays, and telescope observation.
10. Admire the Chicago Skyline from Adler Planetarium
From the Adler Planetarium, you will be able to enjoy what is (in my opinion) the best view of the Chicago Skyline. To enjoy, just go left of the main entrance and follow the small path that surrounds the planetarium.
While you’re in the area, you might want to go for a walk in Northerly Island Park and relax next to Lake Michigan.
11. Visit the Shedd Aquarium
Within the Museum Campus, you can also visit the Shedd Aquarium. Until 2005, it used to be the largest aquarium in the world with almost 19 million liters of water. It contains 1500 species including fish, marine mammals, birds, snakes, amphibians, and insects.
12. Attend a soccer match at Soldier Field.
Chicago is without a doubt a city with a big sports culture. If you’re into American football, then you might consider attending a Chicago Beas soccer match at their stadium Soldier Field.
Things To Do In The Loop or Downtown Chicago
13. Spend almost a complete day at the Art Institute of Chicago
Visiting the Art Institute of Chicago (ARTIC) is a must-do activity during your stay in Chicago. It has over 300,000 art pieces from all over the world and different time periods. In addition, there are always temporary exhibitions available. This makes it the perfect place to visit no matter what sort of art you like.
Among the most famous pieces in this museum are Vincent Van Gogh’s The Bedroom, Katsushika Hokusai’s The Great Wave, American Gothic by Grant Wood, Renoir’s Two Sisters (on a terrace), etc. I could keep on going for a long time.
Good to know: If you are planning to visit the museum, it is interesting to know the following things:
- The Art Institute of Chicago only opens its doors to the public at 11 am. From 10 am – 11 am, it is only open to people with a membership.
- You can buy the tickets at the museum. However, if you want to ensure ticket availability, it is better to buy them online in advance.
- The ticket is valid for the whole day. This means you can visit for a while, exit to get some food and come back later.
14. Take a photo with the Begin of Route 66 sign
Did you know that Historic Route 66 begins in Chicago? The sign where it begins is right in front of the Art Institute of Chicago so make sure to check it out before or after you visit there.
Route 66 used to be a very important route used by immigrants going west in the 30s and it goes from Chicago all the way to Los Angeles. As you can see in the photo, it is just a regular road sign but if you’ve ever been to the West Coast, chances are you have done a bit of this Route while traveling to the Grand Canyon or you might have already seen the end of Route 66 at Santa Monica Pier.
15. Visit the Chicago Cultural Center and be impressed by the Tiffany Dome
The Chicago Cultural Center is famous for having a beautiful dome made of Tiffany Glass. The dome is designed to resemble fish scales and in the center of the dome, we can find the symbols of the different zodiac signs. However, this is not the only remarkable thing about this center. Its halls and stairways are covered in beautiful marble, polished brass, and excellent woodwork that make it an architectural showplace.
Right in front of the entrance of the Chicago Cultural Center, you will find the Chicago Bronze Cow.
16. Attend to an Opera or a Musical at the Lyric Opera of Chicago
The Lyric Opera House of Chicago is one of the leading opera companies in Chicago. It can host up to 3500 people and is the second-largest auditorium in North America. It offers a variety of operas and musicals in its calendar. You can check here what shows are planned during your time in Chicago in case you want to do this.
However, if Opera is not your thing, it is still worth it to visit the building from the outside for its architecture. It consists of 45 story Art Deco tower with two side wings. It also was used as inspiration for the opera house in Citizen Kane movie.
17. Admire Chicago from above from the top of the Willis Tower
Skydeck Chicago is an observation deck located on top of the Willis Tower (originally the Sears Tower). The Willis Tower is a 110-story skyscraper designed by architect Bruce Graham. It opened in 1973 and it held for 25 years the title of the highest building in the world.
The ticket to Skydeck Chicago includes access to The Ledge. These are 4 cubicles completely made of glass that will make you feel you are floating. The first step to enter these cubicles might be a bit scary but once you’re in them you forget about the height.
Good to know: Access to The Ledge cubes is time limited. However, if you go early in the morning and there is no waiting line, the people working there will let you stay as much as you want.
18. Cross DuSable Bridge and be impressed by the different towers surrounding it
DuSable Bridge is a double-deck bridge that bascules and allows Michigan Avenue to extend further north of the Chicago River. The bridge was first named Michigan Avenue Bridge but it was renamed DuSable Bridge in 2010 after Jean Baptiste Point du Sable, Chicago’s first permanent resident.
From the bridge, you can get magnificent views of the Chicago River and the many skyscrapers surrounding it. Among the most famous are the Wrigley Building, the Trump Tower, the Tribune Tower, etc
19. Take an Architecture Chicago River Cruise and learn about the different architectural styles in Chicago
The Chicago Architecture River Cruise is a 1.5h tour that takes you along the Chicago river while the guide explains the different Chicago buildings, how the city was reconstructed after the Great Chicago Fire, and much more. You will learn about the different architectonic styles of the buildings as well as how skyscrapers are built in order to resist the strong winds in the city. There is no better way to admire Chicago architecture than from the river!
Book your Chicago Architecture River Cruise here.
After the tour, if you want to enjoy the architecture at your own pace, you can always enjoy a walk along Chicago’s Riverwalk.
20. Visit Chicago Theater
The Chicago Theater was the first large movie palace in America and it was the flagship of the Balaban and Katz movie theater chain.
The building was built in the French Baroque style and its exterior facade is a mini replica of the Arc de Triomphe in Paris.
Today it is possible to attend music concerts in The Chicago Theater. If you want to do so, you can buy your tickets at their website.
21. Try the Chicago Deep Dish Pizza
Another must-do activity in Chicago is to try the deep-dish pizza. It gets its name due to its cooking style. It is baked in a deep pan which gives the pizza its characteristically high edge. This allows for insane amounts of cheese and chunky tomato sauce.
The best place to try is Giordano’s restaurant which has several different locations all around Chicago.
Good to know: If you want to try Chicago Deep Dish Pizza, you should know that it takes some time to be cooked. So be prepared to wait a little bit for pizza to be served. It also is quite heavy so it is better to not go crazy ordering too much food.
22. Take a tour of the Rookery Building
The Rookery Building is a historic office building in the heart of Downtown Chicago. At 55 meters high, it is considered to be the oldest high-rise in Chicago.
Designed by architects Daniel Burnham and John Root, it is an architectural masterpiece. The lobby is open and free for visitors from Monday to Saturday. However, if you want to really appreaciate all the details in this building you can join one of the tours organized by the Frank Lloyd Wright Trust.
23. Walk under Calder's Flamingo Statue
Another thing to visit in Downtown Chicago is Federal Plaza Square with the famous Red Flamingo by Alexander Calder.
24. Visit the Chicago Board of Trade Building
The Chicago Board of Trade Building is a 44-story art-deco skyscraper. This building is known for its Art Deco architecture, sculptures, and large-scale stone carvings. On its top, there is an aluminum, three-story Art Deco statue of Ceres, the goddess of agriculture.
25. Go for a ride in Chicago's "L" train
When visiting Chicago, you should also get on the elevated “L” train system that works around the Loop neighborhood. Although this is just a regular train, It is quite an experience to ride above the ground between the skyscrapers.
Things To Do In Lincoln Park and Gold Coast Neighborhoods
26. Visit the second statue of Abrahan Lincoln, Lincoln Monument and Gardens
The second statue of Lincoln in Chicago is located in Lincoln Park. It is a 3,7m high bronze statue of Abraham Lincoln by the same artist as the one in Grant Park, Augustus Saint Gaudens. Contrary to the other one, Lincoln is depicted standing in this statue.
27. Go for a swim in Oak Street Beach
If you’re visiting Chicago during the warm summer months, you can enjoy a refreshing swim at one of the beaches of Lake Michigan. Among the most famous ones are Oak Street Beach and North Avenue Beach.
28. Enjoy the beautiful view of Chicago from the Bridge over the South Pond in Lincoln Park
Lincoln Park is a huge park along Lake Michigan named after the 16th president of the US, Abraham Lincoln. It is the largest park in the city and stretches over 11km. This park features a lot of cultural and recreational facilities including 7 beaches, nature reserves, two museums, and even a zoo.
On the southern part of the park, there is a small pond with a bridge crossing over it that offers beautiful views of Chicago.
29. Take plenty of photos from the Honeycomb
Right next to the Bridge over the South Pond, you can also find the People’s Gas Pavilion or The Honeycomb Pavilion. Like its name suggests it is a small pavilion with its roof imitating a honeycomb, located near the Ulysses S Grant memorial statue.
This pavilion was designed by the renowned Chicago Architectural Firm Studio Gang led by Jeanne Gang. It is frequently rented for weddings and different events.
From here, you will be able to take really pretty photos with the Chicago skyline in the background.
30. Relax near the Alfred Caldwell Lily Pool
The Alfred Caldwell Lily Pool, also known as Lincoln Park Lily Pool is a small hidden park within Lincoln Park. It was desinged by Alfred Caldwell and it is the perfect example of the Prairie school landscape design.
The Lily Pool is only open seasonally between April and October.
31. Visit the Ulysses S. Grant Statue in Lincoln Park
The Ulysses S. Grant Monument is a presidential memorial honoring the Civil War general and 18th president of the US, Ulysses S. Grant.
Located in Lincoln Park and not far from the People’s Gas Pavilion, it is a 5,5 meters tall bronze equestrian statue designed by the sculptor Louis Rebisso. At the time of its construction, it was the largest statue of its kind in the United States.
32. Discover natural diversity in the Lincoln Park Conservatory
Lincoln Park Conservatory is a place where you can see year-round displays of plants from many different countries around the world. From giant palms and rubber trees to seasonal flowers, the conservatory offers over 25.000 natural species.
If you want to visit the Lincoln Park Conservatory there are free tours on Fridays, Saturdays, and Sundays.
33. Be impressed by the Chicago Skyline from North Avenue Beach Pier
After you’re done discovering Lincoln Park, make sure to check out the view from North Avenue Beach Pier. You will get to enjoy an amazing view of the Chicago skyline!
Things To Do In The Magnificent Mile and River North
34. Go shopping at the Magnificent Mile
If you want to do some shopping, then you have to visit the Magnificent Mile. This part of Michigan Avenue is full of shops, some of them are high-end shops but there are also more affordable ones. And if you don’t want to do much damage to your bank account, then remember that window shopping is always free!
35. Watch sunset at 360 Chicago
Hancock Tower is another must-visit 100-story skyscraper in Chicago. On its top, on floor 93, you can find 360 Chicago observation deck. As its name suggests, it offers 360-degree amazing views of Chicago. It is the perfect place, to enjoy sunset in the city.
There are different tickets that allow you access:
- Regular admission
- Sip & View: On top of the regular admission, it includes a choice of a drink.
- Tilt & View: Regular admission + Tilt Experience (not recommended for people scared of heights).
- Sip, Tilt & View: A combination of all of the above.
- 360 Sky Yoga Saturdays: General admission and a yoga class with an amazing view (only on Saturdays).
36. Eat some cheese popcorn at Garrets
Garrets is a shop specializing in popcorn. Its first shop opened in 1949 and they were selling CaramelCrisp, CheeseCorn, Buttery and Plein popcorn for 5 cents a bag. Since then, it has become extremely popular and its a must try when in Chicago.
37. Visit the Fourth Presbyterian Church
Right across the John Hancock Center, you can find the Fourth Presbyterian Church of Chicago. This church is the largest Presbyterian congregation in the United States.
The church is quite pretty and it makes a good contrast with the high and modern buildings surrounding it. Make sure to include it in your itinerary and explore its cloister.
38. Visit the Water Tower
Another thing to visit on the Magnificent Mile is the Chicago Water Tower. It is also very close to the John Hancock Tower.
The Water Tower is one of the very few buildings that were built before the Great Chicago Fire and are still standing. Same as the Presbyterian Church, it provides a very big contrast with the modern and high skyscrapers that surround it.
39. Eat a Chicago-style hot dog at Portillo's
Portillos is a retro restaurant chain that specializes in Chicago-style hot dogs which is a hot dog with everything. It is a hot dog with mustard, relish, celery salt, chopped onions, sliced red ripe tomatoes, kosher pickles, and peppers piled into a poppy seed bun.
40. Enjoy some modern art at the Museum of Contemporary Art
The Museum of Contemporary Art or the MCA is an innovative center of contemporary art where visitors can experience the work and ideas of living artists. It is also a way of understanding the historical, social, and cultural context of the art of our time.
In this museum, you will be able to see some of Calder’s mobile art.
41. Relax at Navy Pier
Chicago’s Navy Pier is a pier that is full of attractions, places to eat, exhibitions, and public events. It is the perfect place to go with friends and have some fun while trying some delicious food in a cool and relaxed atmosphere.
While you’re at Navy Pier, make sure to enjoy the view of Chicago from there.
42. Be impressed by The Wrigley Building and Tribune Tower
The Wrigley Building is a symbol of Chicago’s architecture. Place at the beginning of North Michigan Avenue, it consists of two towers connected by a bridge.
Right across the Wrigley Building, you can find the Tribune Tower, a 36-floor neo-gothic tower. The Tribune Tower was home to the Chicago Tribune newspaper until they moved in 2018.
It will be very difficult to miss these two buildings while walking along Michigan Avenue.
43. Take a photo with the famous Wings of Mexico
The sculpture Wings of Mexico is a renowned sculpture by Mexican artist Jorge Marín. It is located at Plaza of the Americas and it is a symbol of perseverance, hope, and diversity.
The sculpture was originally created in México city and has traveled to 25 destinations since then. Among the most famous are Dubai and California.
Note: As of October 1st, 2022 the display is no longer available.
Things To Do In South Hyde Park
44. Watch the Chicago Skyline from Promontory Point
Promontory Point is a man-made peninsula in Lake Michigan in Burnham Park. It was originally created with landfill and in 1930 it was protected with a revetment.
From Promontory Point or The Point, you will get really beautiful views of Chicago and Lake Michigan. It is the perfect spot to go for a walk along the lake and enjoy the views.
45. Fill like in an American College movie while visiting The University of Chicago
The University of Chicago is a private research university established in 1890. Its main campus is in the Hyde Park neighborhood of Chicago between 57th and 59th street and S Ellis Ave and S University Ave.
Walking into the Campus really feels like you have entered an American college movie. While there make sure to visit all the different main campus buildings and the Rockefeller Memorial Chapel.
45. Take a tour of the Robie House
The Frederic C. Robie House which is a single-family house designed by the architect Frank Lloyd Wright. The house was built in 1910 and is a perfect example of the Prairie School, the first architectural style defined as purely American.
It is possible to visit the House and its garden by joining a guided tour. More information about opening times and tour possibilities and prices is on this website: https://www.flwright.org/tours/robie.
46. Visit the Museum of Science and Industry
In Jackson Park, you can find the Museum of Science and Industry. This museum was formerly the Palace of Fine Arts and it is a beautiful building. Even if you are not planning on visiting the museum, the building and the area around it are quite beautiful.
Among the museum’s exhibits, there is a full-size replica of a coal mine, a German submarine U-505 captured during World War II, and the command room of the Apolo 8. If any of these things interest you, then this is your museum for you.
47. Fill completely zen in the Garden of the Phoenix
Garden of the Phoenix is a small Japanese garden within Jackson Park in the Hyde Park district. This garden was created for the 1893 World Columbian Exhibition and represents the friendship and mutual respect between Japan and the United States.
It is the perfect place to go to relax and enjoy a peaceful atmosphere. Particularly during the Cherry Blossom season.
Other Things To Do In Chicago
48. Watch a Chicago Bulls match
While in Chicago you can also go watch a live NBA basketball match. This can be really fun! There is music, the speaker sets the ambiance, during the break you get the cheerleader’s show, and there is also the kissing camera!
Check here if there is any match happening during your stay.
If this is not within your budget, you can always visit the statue of Michael Jordan in the United Center, which is completely free. The statue is also known as The Spirit and it’s a bronze by Amrani. The sculpture was created after Jordan’s retirement following three consecutive NBA championships.
49. Explore Chinatown
Chinatown neighborhood in Chicago is one of the most significant concentrations of Chinese-American in the United States. This makes this area quite interesting to visit. The streets are full of authentic Chinese restaurants and buildings have Asian-style features.
While you’re there make sure to visit the Nine Dragon Wall which was constructed in 2003. Ancient Chinese believed the number 9 to be the most prestigious number and that the dragon is the soul of all things of creation.
50. Remember the movie Untouchables in Union Station
Union Station (Chicago’s train station) is really pretty (both on the outside and the inside) and it is also famous (or at least its stairs are) for appearing in the movie “Untouchables”. On these stairs, Eliot Ness, played by Kevin Costner, had a shoot with Al Capone’s men.
Map With All Things To Do In Chicago
And that’s it for the list of 50 things to do in Chicago. I hope you liked it and found it useful. Let me know what you thought in the comments.
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