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17 Exciting Activities in Chicago (Chicago Must See!)

Last updated on May 10th, 2023 at 07:22 pm

Are you on the hunt for fun activities in Chicago? If yes, then you are in the right place! Chicago is a city full of diverse attractions and sights to enjoy. From world-renowned museums and historical landmarks to scenic parks and lively nightlife, the Windy City undoubtedly has some of the best places to experience. In this Activities in Chicago Travel Guide, we share 17 Chicago Must See ideas. 

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Table of Contents

1. Enjoy the Views From Willis Tower Sky Deck and The Ledge 

One of the top things to do while in Chicago is to visit the Willis Tower skyscraper (note that it was formerly known as the Sears Tower). At 1,451 feet (443 m), it is the second tallest building in the United States and the Western Hemisphere.

Must Do Activities in Chicago: Sky Deck and The Ledge

The Willis Tower Sky Deck and The Ledge are tourist attractions located on the 103rd floor of the tower. Specifically, the Sky Deck is an observation deck that offers stunning panoramic views of the Chicago cityscape.

Comparatively, The Ledge is a glass box that extends out from the side of the building and offers stunning aerial views of the city, as well as affords you the ability to look straight down at the street below. In essence, both are great ways to experience the city of Chicago from above and are the epitome of Chicago’s must-see attractions!

A fun visit in Chicago with Views of Lake Michigan and the Chicago River from one of the most popular Chicago attractions which is Chicago's first glass box.

Fun activities in Chicago include an aerial view of Chicago architecture from the top of the tallest building in Chicago known as  Willis Tower

Fun Fact: You can also visit Wills Tower at night and enjoy stunning views of the city illuminated by millions of lights. It’s an experience you won’t soon forget.

2. Get an Adrenaline Rush at 360 Chicago Observation and The Tilt

Similarly, at 360 Chicago and The Tilt, you will enjoy stunning aerial views of downtown Chicago from the heart of the city.

Must Do Activities in Chicago: 360 Chicago

The 360 Chicago Observation Deck is located on the 94th floor of the John Hancock building. It is one of the city’s most popular spots to take in the scenic sights of Chicago. With its floor-to-ceiling windows, 360 Chicago offers an unobstructed view of sights such as Lake Michigan, Grant Park, Buckingham Fountain, and more.

Spend an afternoon enjoying views of Chicago architecture and some of Chicago's top attractions during a visit in Chicago city. The observation deck at John Hancock Building is one of the top places to visit. Depending on where you stand, you will enjoy stunning city views of Lake Michigan and Chicago River North

Must Do Activities in Chicago: The Tilt

Comparatively, The Tilt offers a different perspective on Chicago’s skyline. You will be strapped into a safety harness before being tilted out over the edge of the building at a 45-degree angle. The views from The Tilt are simply breathtaking! Specifically, you will see Willis Tower (formerly known as Sears Tower), and other iconic landmarks from your vantage point.

Whether you’re looking for a unique way to experience downtown Chicago or simply want to take in some amazing views, 360 Chicago and The Tilt are two destinations to add to your Chicago must’ see bucket list!

3. Explore Millennium Park

Millennium Park is a 24-acre public park in the Loop community area of the city of Chicago. Evidently, it is one of the city’s most popular tourist destinations, and for good reason. It has a variety of public art, including sculptures, art installations, and also landscape architecture.

Activities in Chicago: Millennium Park Features

The park is also the home to the Crown Fountain, which displays a video montage of Chicagoans’ faces on two 50-foot (15 m) towers. Another notable feature of Millennium Park is the famous Cloud Gate sculpture (also known as “The Bean”)

Take a stroll around the city via a fun walking tour or self-guided exploration of one of the top places to visit in Chicago city. Street art also includes the famous art installation known as The Bean. It is located in the famous Millennium Park and in the winter, there is an onsite ice skating rink.

Note that if you plan to visit in the summer, you can enjoy live music/ live performances at the free outdoor concerts that run from mid-June to mid-August. 

Tip: To get a photo by The Bean with nobody around, get there at the crack of dawn. Literally. The sun rises as early as 5:45 am in the summer months!

 4. Ride the Ferris wheel at Navy Pier

Located on the shores of  Lake Michigan, Chicago’s Navy Pier is another Chicago attraction to add to your activities in Chicago itinerary. It features a Ferris wheel, live music (in the summer), a host of restaurants, and more. It is certainly the perfect place to take in the breathtaking sights of Lake Michigan. 

Get the best rates for your Navy Pier experience here.

Fun Fact: Navy Pier is one of Chicago’s most popular tourist destinations, attracting more than 9 million visitors each year.

5. Explore Chicago via a Guided Tour

Without a doubt, Chicago has truck loads of amazing attractions and interesting things to see and do. We recommend including at least one guided tour as one of the best ways to explore activities in Chicago.

There are dozens of different types of Chicago guided tours available.  To that end, no matter what interests you, there’s a Chicago-guided tour that’s perfect for you.

History Tour

 If you’re a history buff, consider taking a guided history tour of some of the city’s most famous landmarks, such as the Sears Tower or the Art Institute of Chicago. 

Food Tour

If you’d rather explore Chicago’s vibrant culinary scene, consider signing up for a food tour. You’ll get to sample dishes from some of the city’s best restaurants. Additionally, you will learn about the history and culture behind Chicago’s culinary traditions. Embarking on a food tour will certainly introduce you to the best local restaurants and cuisines.

Architectural Tour

One unique aspect of Chicago is its architecture. The city is home to some of the most iconic buildings in the world, including the Willis Tower and the Wrigley Building. To that end, if you’re intrigued by the plethora of unique buildings in Chicago, then an architectural boat tour on the Chicago River will be right up your alley.  You’ll learn intriguing history about Chicago’s iconic buildings. Our architectural tour was one of the most fun things we did while in the Windy City! 

Chicago boat tour along the Chicago River to learn about Chicago architecture and the histroy of the second city. Boat tours are fun and great to add to your activities in Chicago itinerary as they  are family friendly
A fun second city boat tour near Chicago river north. Alternatively, you can rent a jet ski and explore.

Bus Tour

If you’re looking for a fun way to get around town, consider signing up for a guided bus tour. You’ll get to see all the major sights and attractions in Chicago without having to worry about navigating through traffic or finding parking. Additionally, you can explore Chicago by night on an open-top panoramic bus night tour.

Helicopter Tour

 And if you’re looking for something truly unique, consider signing up for a helicopter tour or seaplane tour. These aerial tours offer amazing views of Chicago’s skyline and give you a whole new perspective on this world-famous city.

6. Tour the Magnificent Mile District

The Magnificent Mile is another popular place and must-see sight in Chicago. This iconic stretch of North Michigan Avenue runs from the Chicago River to Oak Street.

A visit to the Magnificent Mile is the perfect way to experience some of the city’s best shopping, dining, and architecture. Notable attractions include The John Hancock Center (where 360 Chicago and The Tilt are) and the famed Water Tower Place. 

7. Experience the Shedd Aquarium. 

One of the largest aquariums in North America, Shedd Aquarium is home to thousands of aquatic animals from all over the world. Be sure to check out the famous beluga whales while you’re there!

Tip: Purchase a Chicago City Pass for access to Shedd Aquarium and four other Chicago attractions.

8. Sample Chicago cuisine 

Just the food is a good reason to visit Chicago!   For fine dining, Michael Jordan’s Steakhouse is a great place to start.

Deep Dish Pizza

For the best deep-dish pizza, check out the award-winning Giordano’s, one of the most popular pizza spots in Chicago. 

Tip: Given its popularity, Giordano’s gets pretty busy, with long lines being the norm. Plan accordingly. 

Chicago style deep dish pizza should be added to your activities in Chicago to-do list. Chicago style hot dogs are also some of the best.

Chicago is also famous for its hot dogs. There are many stands throughout the city that sell them. Check out this map to see where they are located. 

For a variety of food options under one roof, check out Chicago’s food halls here. Eat your way through the city’s amazing food scene!

We also highly recommend the South African-founded restaurant Nando’s Peri Peri. Not a Chicago original by any means, but it is still a worthy culinary experience!

Windy City fun  also include the food scene. Consider signing up for a food tour to enjoy some of the city's favorites such as deep dish pizza.
Enjoying a fun food tour in the windy city

For sweet cravings, check out Ghirardelli Chocolate and Ice Cream Shop. It is a popular tourist spot that offers free samples of its chocolates, and it has a wide variety of chocolate treats to choose from.

Another favorite spot for sweets is the Nutella Cafe. Conveniently, it is right next to Nando’s downtown. Note that given its popularity, long lines and wait times is the norm; therefore, plan accordingly.

For the ultimate Chicago food experience, plan your visit to the city around the renowned Taste of Chicago. It is a food festival that is held in Grant Park, in the heart of downtown Chicago, every summer. The festival features food from some of the best restaurants in Chicago, as well as cooking demonstrations, music performances, and more.

Taste of Chicago is a great way to sample some of the best food that Chicago has to offer. It is also a great opportunity to check out some of the city’s most popular tourist destinations!

9. Traverse the Chicago Riverwalk

The Chicago Riverwalk is a  newly renovated 1.25-mile  pedestrian promenade along the south bank of the Chicago River, just east of Michigan Avenue.

This lakefront trail offers stunning views of downtown Chicago and the shores of Lake Michigan. It is a popular spot for walking, jogging, biking, and fishing. Additionally, it is a great place to grab a drink or bite to eat from the wide array of restaurants and bars. 

Fun activities in the windy city include a walking tour along the  Riverwalk

10.  Visit The Zoo

Founded in 1868, the historic Lincoln Park Zoo is one of the oldest zoos in the United States. It is home to over 1,000 animals from around the world, representing nearly 200 species.

Some of the zoo’s most popular exhibits include the Kovler Seal Pool, the Kovler Lion House, and the Regenstein African Journey. The best part is that it is free to visit this zoo! 

11. Explore Notable Sights (Chicago Must See)

Chicago is a city full of history and culture. From the hustle and bustle of downtown to the quieter neighborhoods, there is plenty to explore in the Windy City. One of the best ways to see more of what Chicago has to offer is by taking a walk by some of its most famous landmarks and attractions.

Wrigley Field

One of the first places you’ll want to visit is Wrigley Field, home of the Chicago Cubs. The stadium was built in 1914 and is one of the oldest in the country. The ivy-covered walls and historic charm of the stadium make it a unique experience that you won’t find anywhere else.

Wrigley Building

The Wrigley Building is another Chicago Landmark with a rich history. This iconic building is known for its clock tower, which can be seen from all over downtown Chicago. It is a short walk from other Magnificent Mile sights, such as the John Hancock Center.

Tribune Tower

Another popular tourist destination is the Tribune Tower. This neo-Gothic building was completed in 1925 and is one of the oldest buildings in the city.

Tour of notable activities in Chicago and street art. Consider adding the Museum of Science and Industry, Museum of Science, Children's Museum Campus,  Field Museum Campus, Museum of Ice Cream, Soldier Field and other Chicago museum to your itinerary.

It was formerly the headquarters of the Chicago Tribune newspaper and was considered an iconic symbol of both Chicago and the newspaper industry as a whole. 

University of Chicago

Another historical landmark in Chicago is the University of Chicago. This prestigious university was founded in 1890 and has been responsible for many important advances in science and medicine.

The Chicago Loop 

The Chicago Loop is the downtown district of the city of Chicago, Illinois. It is located on the south side of the Chicago River and is bounded by Lake Michigan to the east and Roosevelt Road to the west.

The Loop is home to some of Chicago’s most famous landmarks and must-see attractions, including Millennium Park, Grant Park, Willis Tower, The Art Institute of Chicago, and The Chicago Theatre.

There are also plenty of fun things to do in the Loop, including shopping, dining, sightseeing, and catching a show at one of the many theaters or music venues.

12. Appreciate Art 

Art Institute of Chicago

Chicago is a city that is rich in art and culture that is bound to pique your interest. As a matter of fact, the Art Institute of Chicago is one of the largest and most famous art museums in the world. It has a permanent collection of over 300,000 objects, including works by Van Gogh, Monet, and American artists such as Andy Warhol and Georgia O’Keefe.

That being said, The Art Institute is not the only place to find art in Chicago. There are also many public art installations throughout the city. Cloud Gate (known informally as “the Bean”) is one such art piece. It is located in Millennium Park (previously mentioned), and is a sculpture made up of 168 stainless steel plates that were welded together. The sculpture has been popular with tourists and locals since it was installed in 2004.

Local Artists

Chicago is home to many talented local artists.   Some of their art can be seen at the Chicago Cultural Center, which features rotating exhibitions of local artwork. Other venues and art galleries that showcase Chicago’s local talent include the Randolph Street Gallery and the Zhou B Art Center. The artists featured at these venues work in a variety of mediums, including painting, sculpture, photography, and mixed media. 

13. Visit Chicago Museums 

The city of Chicago is home to many world-renowned museums, showcasing everything from natural history and science to art and Mexican culture. 

Chicago Children’s Museum

The Chicago Children’s Museum is a great place for families with young children, as it features interactive exhibits and educational programs. 

Field Museum of Natural History

The Field Museum of Natural History is one of the largest natural history museums in the world It offers visitors a chance to see everything from dinosaur fossils to Egyptian artifacts.

National Museum of Mexican Art

The National Museum of Mexican Art is one of the largest museums in the United States that is dedicated exclusively to Mexican art and culture.

Museum of Science and Industry

 If you’re interested in science, the Museum of Science and Industry is unquestionably a must-see! It features thousands of interactive exhibits on everything from weather, to aviation, to electricity, to robotics to space exploration. 

Chicago History Museum

The Chicago History Museum is certainly a great place to learn about the city’s rich history. 

Museum of Icecream

Are you looking for a unique museum experience? Then be sure to check out the Museum of Ice Cream. It features interactive exhibits as well as delicious treats.

Adler Planetarium

If you are a lover of all things astronomy, then add Adler Planetarium to your must-visit list. Expect to explore everything from the planets and stars in our solar system to black holes and galaxies. It is undoubtedly a unique take on a museum experience!

Tip: With a Chicago City Pass, you can enjoy a tour of more than one museum at a fraction of the cost.

14. Relax at Chicago’s Parks and Outdoors

If you’re looking for a place to take a break from sightseeing, why not stop by one of Chicago’s many parks? Note that many of these parks offer unique features and activities that are not found in other parks around the country.

From the iconic Buckingham Fountain to the lush Garfield Park Conservatory, Chicagoans and visitors have plenty to choose from when looking for green spaces to relax. 

Grant Park

One of the most popular parks in Chicago is Grant Park. Located in the heart of downtown, this park offers stunning views of Lake Michigan as well as Buckingham Fountain.

The park is also home to several museums, including the Art Institute of Chicago and the Field Museum of Natural History, as well as several memorials and monuments.

Maggie Daley Park

Another popular park is Maggie Daley Park. This sprawling park covers more than 20 acres and includes a playground, a skating rink, a climbing wall, and more.

Garfield Park Conservatory

Garfield Park Conservatory is one of the largest conservatories in the country. When you visit, you will have an opportunity to explore several different gardens, including a tropical rainforest garden and a desert garden.

The conservatory also hosts special events throughout the year, such as Holiday Flower Show in December and Spring Blooms in March.

15. Catch a Game

As the third largest city in the United States, the Windy City is home to a wealth of professional sports teams. Chicago is a passionate sports town, and the fans are some of the most dedicated in the country!

The Chicago Bulls (basketball), Chicago Blackhawks (ice hockey), Chicago White Sox (baseball), Chicago Bears (American football), and Chicago Cubs (baseball) all compete in the major leagues and draw fans from all over the country.

The Bulls and Blackhawks play at the United Center, the White Sox play at Guaranteed Rate Field, the Cubs play at Wrigley Field, and the Bears play at Soldier Field. 

Whether you are rooting for the Bulls, Blackhawks, White Sox, Bears, or Cubs, while in Chicago, you can come out in full force to support your favorite teams.

Fun Fact: Soldier Field is the oldest standing NFL stadium in the United States.

16. Go to The Beach at Lake Michigan

Chicago is home to some of the most stunning beaches. Miles and miles of pristine shoreline, inviting water, and soft sand make these beaches a top destination and a must-add to your activities in Chicago itinerary. There are plenty of beaches to choose from, but the following are some of the most popular ones:

Montrose Beach

Montrose Beach is located in the Uptown neighborhood on the north side of Chicago. It’s a great spot for swimming, sunbathing, and fishing.

North Avenue Beach

North Avenue Beach is located in Lincoln Park on the north side of Chicago. It’s a great spot for swimming, sunbathing, and windsurfing.

Oak Street Beach

Oak Street Beach is located in Streeterville on the Near North Side of Chicago. It’s a great spot for swimming, sunbathing, and people-watching.

Jackson Park Beach

Jackson Park Beach known as 63rd St. Beach, is located in Hyde Park on the south side of Chicago. It’s a great spot for swimming, sunbathing, and fishing.

17. Save Money at Free Events

Looking for fun and free activities in Chicago? Well then, you are in luck! Despite its tourist destination designation, The Windy City has a host of free events and activities that you can tap into. The following are a few options to consider. 

Attend an Event at Lincoln Park Zoo

As previously mentioned, the Lincoln Park Zoo is absolutely free!  Additionally, all the events hosted by the zoo are free as well. 

Attend an Event at Millennium Park

Millennium Park offers free concerts and movies throughout the summer months.

Attend a Seasonal Event

The free Chicago Air and Water Show is an exciting even that is held every summer.

Explore Events at Cultural Centers

Chicago’s many cultural centers regularly offer special events. Notably, the Chicago Cultural Center is a great place to start. 

Catch a Live Street Performance

From talented musicians to daring acrobats, there is always something exciting to watch on the streets of Chicago. The street performers are very creative, and their performances are quite a sight to see!  

Final Thoughts About Exciting Activities in Chicago

To summarize, the United States is chock-full of must-visit destinations, and Chicago is certainly a great place to experience the uniqueness of the midwest. It is a city that offers endless possibilities for exciting times! Whether you’re looking to explore on your own or opt for guided tours, or a mix of both, there’s something for everyone to add to their Chicago must-see list.

 In view of our experience, the best time to visit is in the warmer months. For this reason, most of the activities we shared are specific to the late spring, summer, and early fall timeframe. Without a doubt, there is fun to be had by first-time visitors, return visitors, and Illinois residents alike! 

In conclusion, we curated this travel guide in the hope that it could be of value to you as you plan your Chicago must-see itinerary. We can’t wait to hear about all of the amazing adventures you will have. Let us know in the comments what activity you will sign up for first. Happy travels! 

Where to Stay in Chicago: Luxury Hotels Near Activities in Chicago

Are you looking for a Chicago hotel near all the must-do activities in Chicago? Check out our Chicago Hotels Travel Guide here.

luxury hotels in chicago travel guide - chicago must see

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The best things to do in the windy city.

Windy City top things to do

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