22 Fun Things to Do in Chicago | 2024 (with Photos)

Natalija Marković

Natalija Marković - Travel Writer

Published: June 30, 2023

Hey there! I'm Natalija, a passionate traveler who has explored the vibrant city of Chicago extensively. With my firsthand experience and love for this incredible city, I'm excited to share with you 22 special and fun things to do in Chicago, providing you with memorable adventures and unforgettable moments.

Fun Things to Do in Chicago

So, you are thinking of visiting the stunning city of Chicago, aka the Windy City.

You'll be pleased to learn that there is more to Chicago than Lake Michigan and the Chicago River, deep-dish pizza, and the Chicago Cubs.

In fact, Chicago is the cultural hub of the Midwest. From walking tours to art galleries and world-class museums, there is something for everyone visiting Chicago.

Read on to discover our list of special and fun things to do in Chicago and start planning your city break today.

Most Recommended Thing to Do

Top Choice Hotel

The Langham Chicago

Our Top Choice Restaurant

Our Top Choice Bar for Nightlife

Best Time to Visit

Summer: vibrant festivals, mild weather, outdoor activities, bustling city.

Average Temperature

Chicago's average temperature is generally cold and variable.

Transportation Options

Buses, trains, taxis, bikes - Chicago has it all.

Average Cost ($, $$, $$$)


My Top Recommendation

Indulge in the city's vibrant food scene by starting your day at a local breakfast joint like Wildberry Pancakes and Cafe, offering a scrumptious selection of fluffy pancakes and mouthwatering omelets - a delightful way to kickstart your exploration of the Windy City.

Take a leisurely stroll along the Magnificent Mile, a bustling shopping mecca with upscale boutiques and flagship stores, or head to Millennium Park where you can marvel at Cloud Gate (affectionately known as "The Bean").

What You'll Need to Bring

  1. Weather-appropriate clothing
  2. Comfortable walking shoes
  3. Travel documents (passport, ID, etc.)

What Not to Miss

  1. Millennium Park
  2. The Art Institute of Chicago
  3. Navy Pier
  4. Willis Tower Skydeck
  5. Magnificent Mile

What to Avoid

  1. Crime-prone areas
  2. Rush hour traffic
  3. Unlicensed taxis

1. Check out Navy Pier on Lake Michigan

Navy Pier on Lake Michigan

This 3,300-foot-long pier on the coast of Lake Michigan supports the Navy Pier Beer Garden.

Grab a beer and a Chicago-style hot dog, and enjoy the view of Lake Michigan or the nearby Chicago River.

Take the walking tour of the Navy Pier, which is an easy walking distance. For those who want a longer walking tour, take a tour down the Chicago Riverwalk leading right into the Navy Pier.

While you're there, check out the nearby Chicago Shakespeare Theater.

2. Explore Chicago Culture with the Chicago Theater

Chicago Theater

The Chicago Theater is a must, for anyone who wants to visit Chicago. Constructed in 1921 it is its own piece of Chicago history and demonstrates some of the amazing architecture of its time.

It is only a short walk from the world-famous Millennium Park and the Chicago River.

The Chicago Theater has it all; plays, music, comedy, and even magic. The Chicago Theater occasionally hosts an art exhibit from the Art Institute of Chicago.

3. Visit the National Museum of Mexican Art

National Museum of Mexican Art

Ready to get out of the cool Chicago air and spend some time inside? Look no further than the National Museum of Mexican Art. This is one of the city's world-class museums, and it boasts a stunning collection of Mexican art.

Discover the rotating art exhibitions, cultural performances, and educational movies on display at the museum. You will even find pieces from students of the prestigious Art Institute of Chicago.

4. Peruse the Fine Art Pieces of the Art Institute of Chicago

Art Institute of Chicago

As one of the most prestigious art institutes in the world, the Art Institute of Chicago is home to thousands of pieces of art from different world cultures throughout history. Moreover, the Art Institute often lends art to world-famous museums and local museums.

The building itself is also a stunning piece of architecture in Chicago. There are free museum days for Illinois residents as well. Now, what's better than free art?

5. Eat Some Chicago Deep Dish Pizza

Chicago Deep Dish Pizza

Chicago deep-dish pizza is a world-famous dish of which the city is very proud.

Grab a Chicago deep-dish pizza anywhere in town. Some of the best Chicago deep-dish pizzas are found in Navy Pier Beer Garden or along the Chicago River.

If you're looking for a pizza with a view, go to the Magnificent Mile and eat a pizza by the 360 Chicago Observation Deck.

Treat yourself to Giordano's classic style deep-dish or Lou Malnati's crispy style deep-dish to experience some of the best in Chicago.

6. Watch the Chicago Cubs Hit a Homerun

Chicago Cubs

When it comes to sports, the Chicago Cubs are a must-see. Located on Chicago's North side you'll find the home of the Cubs, Wrigley Field.

This is one of the most famous baseball parks in the world and provides a great example of Chicago's sports architecture.

On game days, you'll find yourself able to sample Chicago-style hot dogs. If there isn't a game on you'll also be able to take the Wrigley Field walking tour.

The walking tour is worth it just to walk out onto the field. Don't forget to pick up some Cubs memorabilia at the gift shop as well!

7. Visit the Wrigley Building

Wrigley Building

On the other side of the Michigan Avenue Bridge on North Michigan Avenue, you'll find the Wrigley Building.

The Wrigley Building has two over twenty-story towers and is a perfect example of Chicago architecture. Inside is incredible, but the most striking view of the building is from the Chicago River.

Fortunately, this building is one major stop as part of any Chicago architecture river cruise. Furthermore, it can be seen easily as part of the iconic Chicago skyline.

8. Take a Chicago Architecture River Cruise

Chicago River

The best way to see Chicago's architecture is by looking at the city from a boat on the Chicago River.

Any Chicago architecture river cruise will take people past the amazing Willis Tower, (formerly the Sears Tower), the aforementioned Wrigley Building, and the John Hancock Center.

These cruises will also take you along the Chicago Riverwalk, under the North Michigan Avenue Bridge, and end at the Navy Pier.

Some tours will even go along Lake Michigan's lakefront trail.

Don't forget to ask for a picture with Lake Michigan or the Chicago skyline in the background. This stretch of river is an unforgettable experience for anyone visiting Chicago and the Chicago River.

9. Take Your Kids to the Chicago Children's Museum

Chicago Children's Museum

Where do the kids put their art before they can make it into the Art Institute of Chicago? The Chicago Children's Museum of course! This is a museum for 3-8-year-old children.

The museum's location is at the foot of the Navy Pier. Furthermore, this museum is within walking distance of Millennium Park.

Just cross over the Chicago River via the Michigan Avenue Bridge and you'll find the Chicago Children's Museum.

10. Walk Around Millennium Park

Millennium Park

You cannot miss Millennium Park when you visit Chicago. It is located within walking distance of Navy Pier via the lakefront trail and in the middle of Chicago's downtown loop.

Millennium Park is where Chicago's original Baseball stadium burned down during the Great Chicago Fire, so it is a park and a historical landmark for the city.

Nowadays, the park is a beautiful part of Grant Park and a key part of downtown Chicago. It's also a great place from which to view the Chicago skyline.

During the winter, you can even ice skate here.

11. Go See the Cloud Gate and the Crown Fountain

Cloud Gate

While observing the city skyline, one may notice the beautiful pieces of Chicago architecture and art around the park. The two most famous Chicago tourist attractions in Millennium Park are the Crown Fountain and Cloud Gate.

The Crown Fountain is an interactive granite fountain that is the tallest feature of the park.

The Cloud Gate is a reflective piece of art that will distort the city skyline. Both of these features are great photo opportunities. The Cloud Gate is known fondly by locals as The Bean.

12. Explore Maggie Daley Park

Maggie Daley Park

If you loved Millennium Park, why not explore another part of the massive Grant Park? Take the BP Pedestrian Bridge over to Maggie Daley Park. The walk to this other city park has a great view of Lake Michigan as well.

Maggie Daley Park is the best place for ice skating in Chicago. A long ice skating ribbon weaves through the park allowing a view of the area and is a great way to take in the city skyline.

And that is not even close to all Grant Park has to offer.

13. Take in the Beauty of the Buckingham Fountain

Buckingham Fountain

Just to the South of Maggie Daley Park is the glow of Buckingham Fountain. At night the fountain's lights turn on, creating a beautiful light show with the water that dances from the fountain every hour.

Built in 1927, Buckingham Fountain is meant to represent the nearby Lake Michigan. There are four pairs of seahorses on each side of the fountain that represent the four states that border Lake Michigan (Wisconsin, Illinois, Indiana, and Michigan).

Grant Park is worth exploring for Buckingham Fountain alone, but luckily there is still so much more.

14. Observe Sea Life at Shedd Aquarium

Shedd Aquarium

Even further south of Grant Park is the Shedd Aquarium. Just off Lake Michigan, the aquarium houses many species native to the Windy City and the Chicago River.

There are sea creatures from all over the world, including Chicago's own Lake Michigan. The Caribbean Coral Reef attraction is Shedd Aquarium's most popular. It is the top artificial reef in the world.

When you finish seeing all the marine life at Shedd Aquarium, you can explore the Chicago attractions in Grant Park.

15. Experience All the Museum Campus Has to Offer

Field Museum of Natural History

Right next to the Shedd Aquarium is even more downtown Chicago beauty. The Museum Campus houses some of Chicago's treasured historical landmarks.

The Adler Planetarium, America's first planetarium, is right next to Lake Michigan and is a good follow-up to the Shedd Aquarium.

Just south of the Adler Planetarium is another centerpiece of Chicago sports, Soldier Field, home of the NFL Chicago Bears right in the middle of Grant Park. The third heart of Windy City sports is the United Center to the west of Grant Park.

Even the Field Museum of Natural History (aka the Field Museum) is right in the center of the Museum Campus. Take a walking tour of the Field Museum and experience one of the largest museums of its kind.

16. Have a Magnificent Night on the Magnificent Mile

Chicago Riverwalk

Ready to see some amazing architecture? Head to North Michigan Avenue past the Symphony Center, over the Chicago Riverwalk, and back to the tall buildings like the Willis Tower.

Here is the Magnificent Mile of the Windy City. Restaurants galore and sites to see, the Magnificent Mile is the best place in the Chicago River area to take a food tour of the area.

This is the place to get dressed up and go on a romantic date to one of the many fine-dining restaurants. There are even some restaurants at the top of the skyscrapers, like the Willis Tower.

Or if you are looking for something more down to Earth, the Magnificent Mile has plenty of food on the go. The Magnificent Mile is right next to the Chicago River, so grab some food and enjoy it along the Chicago Riverwalk with the Chicago skyline to keep you company.

17. Take in the Chicago Water Tower

Chicago Water Tower

The most popular historical landmark in the Magnificent Mile is the Chicago Water Tower.

While the Water Tower no longer holds water, it does hold a part of Chicago's history. Everything around it burned to the ground during the Great Chicago Fire of 1871, but somehow it survived the fire and still stands today.

Now the Windy City water tower works as a Chicago history museum and as an art gallery, particularly for students of the Art Institute of Chicago. It is the historical hub of the Magnificent Mile.

18. Ride the Elevator up the John Hancock Center

John Hancock Center

The John Hancock Center is the place to go to have the best view of the Chicago skyline. Near the top of the massive building is the John Hancock Observatory (aka the 360 Chicago Observation Deck).

Take in a 360 view of the whole city, from Lake Michigan and the Chicago River to the United Center and even the Art Institute of Chicago.

While the 360 Chicago Observation Deck may not be the tallest location to see the Chicago City skyline (only a mere 1,000 feet above the Magnificent Mile) the floor-to-ceiling windows make for a breathtaking view.

19. View the City Skyline at the Top of the Willis Tower

City Skyline at the Top of the Willis Tower

Our next stop on the Magnificent Mile is the rival tower of the John Hancock Center, the Willis Tower (formally known as the Sears Tower).

As with the John Hancock Observatory (aka the 360 Chicago Observation Deck), the Willis Tower has its own Observation Deck known as the Skydeck which is located on the 103rd floor of the Willis Tower.

Both towers have views of Lake Michigan and Downtown Chicago, but which tower is better between the Willis Tower and the John Hancock Center the subject of a heated debate.

Suffice it to say, both towers will offer the best views of Lake Michigan and the Windy City.

20. Run Around Lincoln Park

Lincoln Park

Once you've visited the 360 Chicago Observation Deck, head to Lincoln Park.

To the North of the Magnificent Mile lies Chicago's largest park, Lincoln Park. Right next to Lake Michigan and in the heart of Second City, Lincoln Park holds many Chicago attractions.

Lincoln Park Zoo lies in the heart of the park. The Lincoln Park Zoo has big cats, gorillas, and penguins, among other exotic creatures. Even better, unlike the Chicago Zoo, it is absolutely free. That makes the Lincoln Park Zoo one of the only free zoos in North America.

North Avenue Beach lies along the coast of Lake Michigan. Despite the Chicago clouds, North Avenue Beach is a beautiful spot to take pictures. During the summer North Avenue Beach has regular lifeguards as well.

Catch the Chicago History Museum just to the South of the Lincoln Park Zoo. The main exhibition is the old rail cars that used to run through downtown Chicago, where Millennium Park is today.

21. Swing By the Chicago Cultural Center by Millennium Park

Chicago Cultural Center

If you enjoyed the Chicago History Museum in Lincoln Park, another option would be the Chicago Cultural Center all the way across the Chicago River back in Millennium Park.

Here, too, you will find art created by the students of the Art Institute of Chicago. Moreover, there is a lot of architecture to see here and it's just a walk away from the Chicago Symphony Center.

The Chicago Cultural Center is where the Mayor of Chicago greets world leaders and diplomats.

22. Smell the Flowers in the Chicago Botanic Garden

Chicago Botanic Garden

The Chicago Botanic Garden is far away from both Lincoln Park and Millennium Park, but it is well worth the drive. The garden opened 50 years ago and has grown to be a very popular and iconic spot in Chicago.

The Chicago Botanic Garden also hosts the Windy City Harvest. It's a very large farmer's market that is worth seeing.

FAQs Relating to Things to Do in Chicago

Let's look at some frequently asked questions related to things to do in Chicago.

What is the number one attraction in Chicago?

The number one attraction in Chicago is the Cloud Gate sculpture. This bean-shaped piece has become one with the city and it is the first image most people conjure to mind when they think of Chicago.

How do you spend a day in Chicago?

You can spend a day in Chicago easily by visiting some of the many museums in the cultural city, as well as taking a river cruise of the architecture and, of course, trying a deep-dish pizza and some Chicago-style hot dogs. You might also visit the Chicago Symphony Orchestra in the evening.

When is the Chicago Blues Festival on?

The Chicago Blues Festival 2024 is taking place between the 8th and 11th of June in Millenium Park. Admission to the festival is free!

Which parks should I visit in Chicago?

While you are in Chicago, you should visit Jackson Park, Oak Park, Garfield Park, and Ping Tom Memorial Park. The Garfield Park Conservatory is a great place to get in touch with nature and take a breath of fresh air.

Summing Up: 22 Fun Things to Do in Chicago

As you can see, there is an abundance of fun and special things waiting for you in Chicago.

Famous for its deep-dish pizza, the stunning Lincoln Park, and vibrant Downtown Chicago, this city has it all. It is no wonder this is a popular tourist destination in the US.

Remember to book all of your tours, tickets, and transport well in advance so you can make sure to see everything. Pack a windbreaker and get ready to enjoy the wonders of Chicago!

There is so much of Chicago to explore. So get out there and explore it this year.