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40 Free & Fun Things To Do In Chicago (Illinois) That Both Adults and Kids Will Love (2024)

What’s up folks! It’s Adam.

I love Chicago. And after my visit this time, I think the beautiful city loves me back. When I think of my favorite thing about this city, I can’t really point at one thing. I think my favorite thing is many different things;[ From architecture to the people.

A few weeks ago I decided to visit the city and see what’s new. The first place I landed was the Adler Planetarium. Watching the solar system is always a fascinating activity for me. Back in my home town, I like visiting planetariums with my friends so I can keep exclaiming to them about how beautiful the solar system is.

I was alone on this one and kept wondering how I was going to survive without telling someone how amazing the solar system looked.

Luckily, the guy next to me just started exclaiming and talking to me about what he was seeing. In no time, we had bonded over our common love for sciences. And just like that a friendship was born. I met his group and we did most activities together. They were such amazing people.

These little tthings are what make Chicago such a lovely city for me.

Chicago is a city in Illinois. It is located on Lake Michigan.

Known as the “Windy City,” Chicago is the third-most populous city in the United States and attracts nearly 58 million visitors a year.

Wondering why so many people visit Chicago?

A city full of fascinating and fun attractions, Chicago boasts some of the greatest museums in the world, along with beautiful waterways, exciting activities, breathtaking architecture, and a rich history that has helped shape the face of the country.

During your visit, you won’t want to miss out on family-friendly activities, such as zoos and magic shows, along with the unique and lively nightlife the city has on offer.

Unquestionably, the city is overflowing with attractions, so in order to help you get started, a list of the fun things to do in Chicago is listed below.

Take one of the many tours provided in the city, discover interesting locales and foods, or relax and enjoy the outdoor areas that are both scenic and filled with an array of activities everyone will enjoy.

Table of Contents

Things To Do In Chicago:

1. Chicago History Museum

Thomas Barrat | Shutterstock

Rating: 4.6★

Entry Ticket: Adults: $19.00, Seniors and Students: $17.00, Ages 12 and Under: Free

Address: 1601 North Clark Street, Chicago, IL 60614

  • Open Tuesday through Saturday, 9:30 am – 4:30 pm, Sunday, noon – 5:00 pm
  • Allow 2 – 3 hours

Before doing anything else, start out a trip to Chicago is the Chicago History Museum.

While there, you will be immersed in the history of the city through stories shared in the many exhibits on display.

With a history as fascinating as the collections it boasts, the museum recovered from the Great Chicago Fire in 1871 as a result of large purchases of manuscripts, paintings, and artifacts.

Are you ready to learn about Chicago’s fascinating history?

During your tour of the museum, you will be able to view beautiful displays of clothing collections, photographs that explore the history and diverse communities of Chicago, in addition to artwork that tells the story of the Great Chicago Fire.

Moreover, you can even watch a film that will provide you with the true history and experience of the city.

Overall, if you make your way to this inspiring and educational museum, you will find a fascinating journey into the story of Chicago.

2. Visit the Skydeck Chicago at Willis Tower

Sonja Weiss | Shutterstock

Rating: 4.5★

Entry Ticket: Adults: $34.50, Children: $26.50, Ages 2 and Under: Free

Address: 233 South Wacker Drive, Chicago, IL 60605

  • Open daily
  • Recommend booking tickets in advance
  • VIP dinner: $100.00 per person, limit of 2

Previously known as the famous Sears Tower, The Willis Tower, is the third tallest building in the Western Hemisphere, consequently making the Skydeck Chicago experience a once-in-a-lifetime opportunity.

Ready to experience the best view of Chicago?

If you are daring enough (and not afraid of heights), you will have the thrill of seeing Chicago from 1,353 feet in the air while you stand on a glass ledge that also extends approximately 4 feet out from the building.

View the undeniably breathtaking city while it sweeps out beneath you, with sparkling buildings, winding rivers, and bustling city streets.

For a date night that is unforgettable, you may want to purchase a VIP dinner for two, in which you and your date can dine on classic Chicago pizza as you enjoy the incredible nighttime view of the city from the glass ledge.

Among the most exciting things to do in Chicago, you won’t want to miss out on the rare opportunity offered by Skydeck Chicago.

3. 360 Chicago

Tilting glass at John Hancock Center observation area. Alex Cimbal | Shutterstock

Rating: 4.6★

Entry Ticket: Starting at $30.00

Address: 875 North Michigan Avenue, Chicago, IL 60611

  • Open daily
  • TILT ride is an additional fee

If you would like an even more adventurous experience while viewing Chicago from above, you’ll want to check out 360 Chicago, located in the John Hancock building.

Not only will you get to see Chicago from a height of 1,000 feet, but you will have the ultimate experience as you face downward in the glass observation deck, allowing you to feel as though you are floating above the city.

While intimidating at first, you won’t regret the thrilling experience as you tilt forward while standing behind a window of glass, creating an unforgettable and exhilarating moment.

If you’d rather skip the tilt ride, you can also just sit back and enjoy the view from a regular seat, and with a bar on offer, you even have the option of enjoying a cocktail as you relax and watch the sun set over the city.

Take the time to visit this observation deck that provides an unusual and exciting experience.

4. Lakefront Trail

James Andrews1 | Shutterstock

Entry Ticket: Free

Address: Ardmore Avenue North to 71st Street South, Chicago, IL

  • Open year-round
  • Pet-friendly

For some of the best views near and around Chicago, Lakefront Trail is the perfect option if you want to also have some outdoor activity while sightseeing.

The 18-mile trail runs along the edge of Lake Michigan and connects to various beaches, parks, and amenities, such as bicycle rentals.

Take a leisurely stroll, go for a jog, or get your pet out for some exercise while viewing the iconic Chicago skyline, the tranquil waters of the lake, and bustling shopping areas that are perfect for people watching.

Going on a trip along the Lakefront Trail is a great way to not only see the city’s spectacular buildings but a chance to get some fresh air and unwind.

5. Catch a Baseball Game at Wrigley Field

Steve Broer | Shutterstock

Rating: 4.8★

Entry Ticket: Game tickets starting at $57.00, Ballpark tour starting at $30.00

Address: 1060 West Addison Street, Chicago, IL 60613

  • Check schedule on website
  • Allow 90 minutes for tour

A particularly iconic staple of Chicago is its baseball team, the Chicago Cubs, in addition to their home base, Wrigley Field.

As well as being an American staple, it is the oldest National League ballpark in the world, having opened in 1916.

If you are lucky enough to be in Chicago during baseball season, you will want to attend a game, immersing yourself in a local passion, where you can dine on a classic ballpark hot dog, feel the thrill of the crowds around you, and cheer on the home team.

For those who aren’t there during the season or simply aren’t interested in a game, you can go on a fascinating tour of the legendary ballpark, learning its illustrious history as you tour the clubhouse and dugout, walk the field, and get a close-up view of the famous ivy on the outfield wall.

A classic symbol of Chicago, a visit to this ballpark for either a game or a tour will be a fun and enjoyable excursion.

6. Magnificent Mile

The magnificent mile brown color street sign, City high rise buildings background, closeup view. Rawf8 | Shutterstock

Rating: 4★

Entry Ticket: Free

Address: North Michigan Avenue, Chicago, IL

  • Allow at least 3 hours
  • Open year-round

A great excursion while in Chicago, the Magnificent Mile is a lively area of the city where you can find just about anything.

Stroll the 13-block area that is in the heart of the city as you peruse hundreds of stores and restaurants, numerous entertainment venues, and classic Chicago attractions.

Find the perfect gift or souvenir, then head over to dine on casual cuisine, fresh seafood, or global dishes at one of the many specialty restaurants on offer.

While perusing Magnificent Mile’s diverse area, you’ll be able to visit an array of museums, take a cruise, appreciate Chicago architecture, and enjoy live music in a variety of venues.

From time to time, take a break and stop by the local tea shop for a pastry and a delicious warm drink.

7. Three Dots and a Dash

@Three Dots and a Dash

Rating: 4.5★

Entry Ticket: Free

Address: 435 North Clark Street, Chicago, IL 60654

  • Open daily, 4:00 pm to midnight
  • Must be 21 or older

Named for the Morse code that translates to “victory,” Three Dots and a Dash combines the secretive and exclusive feel of a speakeasy with a distinctive tropical experience below the streets of Chicago.

One of the top fun things to do in Chicago at night, you will have an exceptional experience, whether it be taking your significant other on a date or hanging out with friends.

Dine on authentic tropical fares, such as Thai fried chicken or coconut shrimp, while enjoying the atmosphere provided by Polynesian décor that includes tiki glasses, totems, and tropical plants.

Specializing in rum, you’ll want to sample some of the drinks on offer that hail from various tropical regions, such as Puerto Rico, Panama, and the Dominican Republic.

Above all, have a night full of fun and relaxation at Three Dots and a Dash, where you will have an immersive tropical experience right in the heart of Chicago.

8. Chicago’s First Lady Cruises

LittlenySTOCK | Shutterstock

Rating: 4.8★

Entry Ticket: Starting at $51.96

Address: 112 East Wacker Drive, Chicago, IL 60601

  • Book in advance
  • Family-friendly
  • Allow 90 minutes

Interested in getting out on Chicago’s famous riverways?

Chicago’s First Lady Cruises provides a one-of-a-kind sightseeing experience while in the “Windy City,” with luxury yacht tours that take you right through the center of Chicago along the breathtaking waterways of the city.

Choose from three tour experiences – an architecture cruise, an evening river cruise, or a photography cruise.

Learn about the history and influences of the city’s architecture while you glide down the Chicago River, with docents also on hand to provide you with stories and information that are undeniably fascinating and educational.

For a romantic excursion or simply a great way to view the sunset, the evening river cruise provides you with a cocktail, in addition to relaxed conversation as you view the changing sky against the mirror of buildings.

Have your camera at the ready for the early morning cruise through Chicago on the photography tour, where points of interest will be easily seen, allowing you to get that perfect photo while on your trip.

A superb way to view Chicago, Chicago’s First Lady Cruises is an exceptional experience for anyone visiting the city.

9. Peggy Notebaert Nature Museum

The nature, science museum plans a new, $4 million exhibit, Nature’s Playspace, for children ages 6 and up. Pamela Brick | Shutterstock

Rating: 4.6★

Entry Ticket: Adults: $9.00, Seniors and Students: $7.00, Children: $6.00, Ages 3 and Under: Free

Address: 2430 North Cannon Drive, Chicago, IL 60614

  • Open daily
  • Kid-friendly

An opportunity to connect with nature on a whole new level is provided by the Peggy Notebaert Nature Museum.

As soon as you arrive, you will be encouraged to learn about the world around us through immersive experiences.

If you are searching for fun things to do in Chicago with the kids, look no further than this nature museum, where both you and your child will discover a fascinating world of butterflies, artwork, and wildlife, along with much more.

Moreover, you and your child will learn about the importance of rivers and how they are vital to ecosystems around the world, in addition to how climate and weather affect our lives everywhere.

Also, you will be delighted with a visit to the laboratory where you can feed turtles.

Take your child to this unique museum in Chicago and allow both of you to be educated and immersed in an unforgettable experience.

10. Chicago Food Tours

Andrey Bayda | Shutterstock

Rating: 5★

Entry Ticket: Starting at $50.00

Address: Chicago, IL

  • Book in advance
  • Family-friendly
  • Allow 3 hours

Chicago Food Tours is an experience like no other, allowing you to choose what type of food you want to sample while also discovering diverse Chicago neighborhoods.

Ready to try some of the best food Chicago has to offer?

Sample food from Chinatown while you explore the neighborhood with your knowledgeable guide.

Additionally, head to Pilsen, where you can dine on some of the best tacos you’ve ever tasted while sipping premium tequila.

For a true taste of Chicago, you might want to take an iconic foods tour.

During the tour, you will get to sample some of the staple fares the city has to offer, from deep dish pizza to mouthwatering Italian subs.

All in all, Chicago Food Tours has whatever you are craving, with a wide range of choices that will leave you satisfied.

11. Chicago Symphony Orchestra

Igor Bulgarin | Shutterstock

Rating: 4.8★

Entry Ticket: Varies according to event

Address: 220 South Michigan Avenue, Chicago, IL 60604

  • Book in advance

Founded in 1891, the Chicago Symphony Orchestra is considered one of the finest orchestras in the world, with not only performances provided in Chicago but also tours that take them throughout the country.

For a night of beautiful and moving music, you’ll want to attend one of the many concerts the orchestra offers.

While attending a concert, you will be able to listen to world-renowned conductors sharing music by artists such as Ravel, Tchaikovsky, and Beethoven, in addition to many others. 

You will be undoubtedly delighted by the impressive performances of the musicians who belong to this nationally acclaimed orchestra while you sit back inside the historic Symphony Center that was built in 1904.

12. Soldier Field

Larry1235 | Shutterstock

Rating: 4.6★

Entry Ticket: Varies according to event

Address: 1410 Special Olympics Drive, Chicago, IL 60605

  • Allow 1 – 2 hours
  • Check schedule on website

While mostly being known as home to Chicago’s NFL team, the Bears, Soldier Field also offers year-round events, such as music, soccer games, and charity events, in addition to physical exercise classes open to the public.

Catch a football game and root for the home team if you are in Chicago during football season, or take a tour of the stadium, where you will visit the stadium’s courtyard and landmarks, walk the field, and have the opportunity to see the locker room.

You will also be able to learn the history of the stadium as you get to experience what it’s like to sit in the skyline suite, where you can look over the entire stadium.

Visit this iconic Chicago spot, where you can immerse yourself in the fans and community that make up the city.

13. Field Museum

Schusterbauer | Shutterstock

Rating: 4.7★

Entry Ticket: $27.00

Address: 1400 South Lake Shore Drive, Chicago, IL 60605

  • Open daily, 9:00 am – 5:00 pm
  • Kid-friendly
  • Allow 3 – 4 hours

With a collection of over 40 million artifacts and specimens, the Field Museum is one of the best things to do in Chicago with the family, with natural history exhibits that will both delight and amaze.

You will certainly want to meet Sue, the fossil skeleton of a Tyrannosaurus Rex, before visiting a model of Lucy, a 32-million-year-old hominid discovered in Ethiopia.

Afterward, tour the Hall of Gems and see everything from natural crystals to a 97.45-carat ruby, in addition to many other dazzling displays.

From Native American exhibits to displays from ancient Egypt, you and your family will discover fascinating artifacts.

With interactive displays, such as a Māori meeting house to nature walk expeditions that showcase wildlife and ecosystems from around the globe, this unique museum experience is unforgettable.

14. Buckingham Fountain

Rudy Balasko | Shutterstock

Rating: 4.7★

Entry Ticket: Free

Address: 301 South Columbus Drive, Chicago, IL 60605

  • Open in summer
  • Located in Grant Park

Check our list of best hotels near Grant Park Chicago!

Looking for one of the most recognizable spots in Chicago?

One of the largest fountains in the world, Buckingham Fountain has become an iconic landmark in Chicago.

Spectacular water shows coupled with its sheer size attracts visitors from around the world to the fountain.

Visit this fountain, and you will be particularly delighted by the displays that are shown for 20 minutes every hour.

After dark, visitors are awestruck by a breathtaking light and sound display, providing music while vibrant colors also accompany the jets of water that reach up to 150 feet in the air.

A perfect spot for a photo opportunity, along with a chance to simply unwind and watch the show, this fountain is a must-see while in Chicago.

15. Rosa’s Lounge

Sara Muñoz Hermoso | Flickr

Rating: 4.8★

Entry Ticket: $15.00

Address: 3420 West Armitage Avenue, Chicago, IL 60647

  • Open Tuesday through Saturday, 8:00 pm – 2:00 am
  • Must be 21 or older

Do you want to find one of the best spots in Chicago for blues music?

Along with all the many things Chicago is known for, blues music is among the top, and Rosa’s Lounge provides one of the top things to do in Chicago at night with great music, cocktails, and a traditional blues lounge atmosphere.

Sample one of the many specialty drinks offered at this lounge, such as Billy Branch’s Blues Shock or a Sunday Kind of Love, as you enjoy a variety of blues artists that will knock your socks off.

Previously, legendary performers, such as Melvin Taylor and Pinetop Perkins, have performed at the lounge, letting you know you will be in for a treat while making a visit to this family-owned blues lounge.

16. Garfield Park Conservatory

Nagel Photography | Shutterstock

Rating: 4.8★

Entry Ticket: Free

Address: 300 North Central Park Avenue, Chicago, IL 60624

  • Open Wednesday through Sunday, 10:00 am to 5:00 pm
  • Book in advance
  • Allow 1 – 2 hours

Covering a 184-acre area, Garfield Park Conservatory is an urban oasis in the heart of the city.

Wondering how to relax while in Chicago?

Stroll through the outdoor gardens, discovering a variety of plants and landscaped paths, in addition to lovely water installations.

You’ll also want to tour the Fern Room and Palm Room, where you can get a glimpse of what Chicago may have looked like millions of years ago or enjoy towering palms that create a tropical escape.

The Desert House is a must-see while at the conservatory, with a large and exotic collection of succulents and cacti, some of which are over a century old.

Immerse yourself in nature while in Chicago at the Garfield Park Conservatory, where you will discover so much more than flowers.

17. Chicago Detours

Rawf8 | Shutterstock

Rating: 4.9★

Entry Ticket: Starting at $39.00

Address: 53 West Jackson Boulevard #1357, Chicago, IL 60604

  • Book in advance
  • Allow ½ day

With Chicago Detours, you get more than just a tour of the city.

Chicago Detours offers a variety of tour options, such as private customized tours, neighborhood tours,  and also bucket list tours that chiefly give you a taste of some of the city’s iconic sites.

Moreover, you will view the Chicago skyline and visit murals while you learn about Chicago from historians and teachers.

Want to get to know the Chicago locals?

Immerse yourself in Chicago’s community by visiting dive bars where you can grab a drink before listening to stories about the local architecture.

Chicago Detours is a committed, knowledgeable tour company that is passionate about Chicago and will pass that enthusiasm on to you during your tour.

18. Lincoln Park Zoo

The zoo is a 35-acre zoo in Lincoln Park, Chicago, Illinois, which is the fourth oldest zoo in North America. Jay Yuan | Shutterstock

Rating: 4.6★

Entry Ticket: Free

Address: 2001 North Clark Street, Chicago, IL 60614

  • Open daily, 10:00 am – 5:00 pm
  • Allow 2- 3 hours

Founded in 1868, the Lincoln Park Zoo covers 35 acres and is the only free zoo in the state of Illinois.

Along with numerous animal habitats to visit, you and your family will be pleased with the other attractions offered as well, such as the carousel, which showcases endangered animals, cafes located throughout the zoo, a small train adventure, and areas to rest and relax.

Take a tour of penguin cove, view a swamp monkey at the primate habitat, or watch a red kangaroo bounce through its natural environment.

In addition to the numerous animals you can see up close, the zoo takes pride in its extensive landscaping that features unique gardens where you can see everything from vibrant tropical flowers to unusual trees and shrubs.

The perfect family excursion while in Chicago, the Lincoln Park Zoo is a fantastic outing that everyone will love. 

19. Take a Tour with Tall Ship Windy

Alvov | Shutterstock

Rating: 4.6★

Entry Ticket: Starting at $17.00

Address: 600 East Grand Avenue, Chicago, IL 60611

  • Book in advance
  • Allow 2 hours

Tall Ship Windy offers sailing tours near and around Chicago, with several options for themed, educational, and classic sailing tours.

If you want to view the spectacular skyline of Chicago from the water, you have the option to take a leisurely sail along Lake Michigan.

You can learn about the architecture during your lakefront cruise.

Additionally, for a nighttime excursion, you can’t go wrong with the fireworks cruise.

Sip a cocktail and also enjoy fantastic fireworks while you glide by the city.

In the mood for some pirate-style drinking?

With the Pirate’s Pub Sail you will have a fun-filled time sampling beer and singing traditional pirate songs, all while floating across Lake Michigan.

A unique and special experience awaits you with Tall Ship Windy and their exceptional sailing tours.

20. Adler Planetarium

Henryk Sadura | Shutterstock

Rating: 4.3★

Entry Ticket: Starting at $19.00

Address: 1300 S DuSable Lake Shore Drive, Chicago, IL 60605

  • Open Friday through Monday, 9:00 am – 4:00 pm, Wednesday, 4:00 pm – 10:00 pm
  • Allow 2 – 3 hours

Adler Planetarium hosts nearly half a million visitors each year.

People from around the world are especially attracted to the museum’s dedication to connecting the community with the universe and each other.

During your visit, you will be able to tour exhibits that range from astronomy’s impact on culture throughout history to the night sky of Chicago, interactive displays about the moon missions, and an experiment lab, where children are encouraged to play and create.

While at the planetarium, you’ll also want to attend at least one show, which includes a space tourism tour where you and your family can travel the solar system in the year 2096.

A once-in-a-lifetime experience, Adler Planetarium is something you and your family will love while in Chicago.

21. Free Chicago Walking Tours

Jacob Boomsma | Shutterstock

Rating: 4.9★

Entry Ticket: Free

Address: Chicago, IL

  • Book in advance
  • Allow 2 hours
  • Family-friendly

Among the fun, free things to do in Chicago, Free Chicago Walking Tours is certainly one of the best.

While booking your excursion, you will have numerous tour options of the city that are led by experienced guides.

Would you like to see Chicago’s architecture up close?

Learn about the amazing architecture of Chicago as you make your way through some of the city’s most iconic buildings, such as the Palmer House Hotel and Marquette Building.

In addition, you will have the opportunity to see little-known gems of the city, walk along the Chicago River, tour historical gangster sites, and also enjoy a public art tour.

Moreover, see the famous “bean” at Millennium Park or visit historic neighborhoods.

By the same token, you can view state buildings, impressive brownstones, and spectacular mansions.

Take a tour with Free Chicago Walking Tours and allow yourself the pleasure of being immersed in the city and its community while learning about its heritage.

22. North Avenue Beach

Artesia Wells | Shutterstock

Rating: 4.6★

Entry Ticket: Free

Address: 1600 North Jean-Baptiste Point, DuSable Lake Shore Drive, Chicago, IL 60614

  • Open daily
  • Dogs not allowed

Wondering if Chicago has any beaches?

A undeniably great way to get outdoors and enjoy some summer weather in Chicago is North Avenue Beach, where there are numerous activities and attractions that will certainly please anyone, both young and old.

At the beach, you will find a charming and spacious beach house that gives visitors exceptional views of the city skyline.

In addition, you will find typical beach activities, such as swimming, bicycle and paddleboard rentals, yoga, kayaking, and jet skis.

Spend some time playing in the water before playing a game of roller hockey.

Afterward, head over to one of the concessions stands or restaurants offered.

Enjoy some fresh air and beach time in Chicago during your visit while you relax and unwind.

23. Six Flags Great America

Marti Bug Catcher | Shutterstock

Rating: 4.4★

Entry Ticket: Starting at $34.99

Address: 1 Great America Parkway, Gurnee, IL 60031

  • Open Tuesday through Sunday

If you are searching for great things to do with the kids near Chicago, you’ll want to be sure to head to Six Flags Great America which is located approximately 1 hour from Chicago.

While at this amusement park, you’ll find thrills and excitement on rides such as Batman, where you will speed through the air like a bat, or the demon, a rollercoaster for only the bravest visitors.

As well as thrill, there are attractions that are more low-key.

Take your kids on a more placid ride, such as Big Easy Balloons before experiencing the Scenic Railway train.

Undoubtedly, your whole family will enjoy the diverse and numerous rides.

Moreover, you’ll also want to check out live shows, such as an interactive drum show, character dance party, and much more.

During your visit to Six Flags Great America, you will discover thrills and excitement with your kids .

24. The Art Institute of Chicago

The Art Institute of Chicago has one of the world’s most notable collections of Impressionist. MaxyM | Shutterstock

Rating: 4.8★

Entry Ticket: Adult: $25.00, Seniors, Students, and Children: $19.00, Ages 3 and Under: Free

Address: 111 South Michigan Avenue, Chicago, IL 60603

  • Open Thursday through Monday, 11:00 am – 5:00 pm
  • Allow at least 3 hours

Founded in 1879, The Art Institute of Chicago boasts an surprisingly diverse and large collection of artworks, from classical paintings to abstract art installations.

For example, you’ll discover Buddhist sculptures dating back hundreds of years and works by famous artists such as Van Gogh and Diego Rivera.

Equally important, the museum displays other lesser-known pieces from around the world.

While at the museum, you will have the once-in-a-lifetime opportunity to view such world-renowned works as A Sunday on La Grande Jatte by Seurat, American Gothic by Wood, and Claude Monet’s Water Lillies, in addition to Two Sisters by Renoir.

Take the time to visit the spectacular and remarkable art housed here during your visit to Chicago.

25. Maggie Daley Park Ice Skating Ribbon

Big Joe | Shutterstock

Rating: 4.6★

Entry Ticket: Free

Address: 337 East Randolph Street, Chicago, IL 60601

  • Open November – March
  • Family-friendly

Are you looking for Chicago activities during the holidays?

During the snowy months of the year, you’ll want to head to Maggie Daley Park Ice Skating Ribbon for one of the top best things to do in Chicago in the winter.

Running ¼ of a mile in length, the ice skating ribbon winds its way through Chicago, creating a particularly magical winter experience that you’ll want to share with your loved ones.

Along the path of the ribbon, you will see a 40-foot climbing wall that can be used by guests for an additional fee.

Meanwhile, hot chocolate stands allow you to warm up in between trips up and down the ribbon.

Enjoy the views of Chicago in the winter wonderland of this ice skating spot that has become an icon for not only visitors but also the local community.

26. UP Comedy Club – The Second City

Fer Gregory | Shutterstock

Rating: 4.6★

Entry Ticket: Starting at $10.00

Address: 230 West North Avenue, Chicago, IL 60614

  • Open daily
  • Book in advance

While in Chicago, take the time to get some laughs at UP Comedy Club, one of seven clubs that are part of The Second City Franchise.

At UP Comedy Club, you will be able to watch stand-up comics, improv, and also sketch comedy, all while sipping a cocktail and enjoying a mouthwatering dinner.

Dine on casual American cuisine as you watch comedy sketches that tell hysterical Chicago stories, to say nothing of stand-up comedians that will tickle your funny bone with their songs and jokes.

Similarly, improv performers that will make you cry with laughter.

Have fun with a night of laughs from the UP Comedy Club in Chicago during your visit.

27. Chicago Sports Museum

@Chicago Sports Museum

Rating: 4.5★

Entry Ticket: Adults: $10.00, College Students: $8.00, Seniors and Children: $6.00, Ages 3 and Under: Free

Address: 835 North Michigan Avenue, Chicago, IL 60611

  • Open Monday through Saturday, 11:30 am – 7 pm, Sunday, noon – 6:00 pm
  • Family-friendly
  • Allow 2 hours

Chicago is home to some of the most well-known sports teams and athletes around the world, from Michael Jordan of the Bulls to Gale Sayers of the Bears.

The Chicago Sports Museum gives visitors a truly unique experience while also providing a look behind the scenes with interactive exhibits that will engage you, your family, and friends.

While at the museum, you will have the opportunity to test your vertical leap against Michael Jordan.

Additionally, compare your grip strength to Kyle Long before trying on a replica of William “Refrigerator” Perry’s Super Bowl Ring.

You’ll also want to check out the Hall of Legends, where VR games await you to test your skills and trivia knowledge about Chicago teams, along with the World Series exhibit, where you can view John Madden’s Championship rally t-shirt or Addison Russell’s Grand Slam ball.

Not only for avid sports fans, this museum combines entertainment and education, giving you a fun-filled experience.

28. Oz Park

Lost in the Midwest | Shutterstock

Rating: 4.6★

Entry Fee: Free

Address: 2021 North Burling Street, Chicago, IL 60614

  • Open daily
  • Walking tours available
  • Pet-friendly

An activity that is one of the free things to do in Chicago with kids is Oz Park.

You and your children can play while immersing yourself in the world of The Wizard of Oz.

Named for famous Chicago resident Frank Baum, the author of The Wonderful Wizard of Oz, the small park has numerous activities and attractions, such as tennis courts, gardens, and ball fields.

Certainly you will want to stroll through the Emerald Garden while you enjoy the vibrant flowers.

Moreover, stop by the statues of Dorothy and her friends to snap some pictures, in addition to letting your kids swing and climb at Dorothy’s Playlot.

A fun day of games and relaxation awaits you and your family at this one-of-a-kind park in Chicago.

29. Have a Slice of Pizza at Burt’s Place

Aleksei Isachenko | Shutterstock

Rating: 4.6★

Entry Ticket: Free

Address: 8541 Ferris Avenue, Morton Grove, IL 60053

  • Open Tuesday through Sunday, beginning at 4:30 pm
  • Family-friendly

Have you ever wondered why Chicago is famous for its deep dish pizza?

Look no further than the legendary pizza maker, Burt Katz.

Burt Katz is a legend in the world of classic Chicago deep dish pizza, having opened his first restaurant in 1965, eventually earning world renown for his mouthwatering creations.

His pizza was so good, in fact, that Anthony Bourdain was quoted as saying, “Burt’s Pizza was the only deep dish pizza I ever loved.”

Today, Burt’s Place keeps his tradition of amazing food alive with classic Italian toppings, simple recipes, and perfectly cooked pizzas.

Relax in the atmosphere of this restaurant as you dine, read framed newspaper articles about the “Kinda Cranky Pizza Guy,” or enjoy some outdoor time on the patio.

Visit this iconic pizza place for a late lunch or dinner, and taste some of the best deep dish pizza in the world.

30. Shedd Aquarium

Jason Patrick Ross | Shutterstock

Rating: 4.6★

Entry Ticket: Adults: $39.95, Children: $29.95, Ages 2 and Under: Free

Address: 1200 South DuSable Lake Shore Drive, Chicago, IL 60605

  • Open daily
  • Allow 3 hours
  • 4D tour upgrade available

Home to nearly 32,000 animals, Shedd Aquarium, is a must-see while in Chicago, with its fascinating exhibits and diverse marine life.

Using an audio guide, tour exhibits like Underwater Beauty, where you will view vibrant fish and rare and unusual marine life.

You’ll also want to take a trip through the Caribbean Reef, where you can view sharks, rays, sea turtles, and colorful angelfish as they glide through the waters of the aquarium.

Among the other exhibits on offer are habitats from the Amazon, lakes, rivers, and even a stingray touch area.

You’ll also want to view the spectacular jellies, impressive Giant Pacific Octopus, and wide range of reptiles before taking a break and heading to the aquarium’s terrace, where you can relax and view the Chicago skyline.

31. Trickery 

@Trickery Chicago

Rating: 4.9★

Entry Ticket: $41.00

Address: 3453 North Halsted Street, Chicago, IL 60657

  • Open Thursday through Sunday
  • Book in advance

Enjoy a night of magic, laughs, and entertainment at Trickery, where you will be both amazed and amused.

A hidden gem of Chicago, Trickery is a magic show geared toward adults, where you can see the tricks up close as the performer also entertains you with a huge and hilarious personality.

Watch a variety of tricks that will keep you guessing as the magician selects audience members to participate, ensuring everyone has a great time.

While drinks aren’t available at this theater, you can bring your own, and snacks are sold at a minimal cost, so sit back and relax as you let your worries be carried away.

32. Tour Graceland Cemetery

Thomas Barrat | Shutterstock

Rating: 4.7★

Entry Ticket: Free

Address: 4001 North Clark Street, Chicago, IL 60613

  • Open daily, 8:00 am – 4:00 pm
  • Virtual tour available on website
  • Bring camera

Home to spectacular sculptures and famous gravesites, Graceland Cemetery, is not only beautiful but a great way to get historical Chicago references.

Through a virtual tour that can be found on the cemetery’s website, you will find the resting places of the founder of Major League Baseball, William Hubert; Allan Pinkerton, who founded the secret service; and Jack Johnson, the first African American heavyweight boxing champion.

Along with the numerous gravesites you’ll want to visit are sculptures and tombs famous for their beauty and unique design.

You’ll also want to give attention to the 150-year-old cemetery’s spectacular landscaping and burial monuments, many designed by world-renowned architects.

While a trip to a cemetery may sound macabre, Graceland Cemetery is much more than what it seems, with breathtaking beauty and a deep Chicago history ready to be shared.

33. WNDR Museum

Kelly Loris | Flickr

Rating: 4.2★

Entry Ticket: Adults: $30.00, Children: $25.00

Address: 1130 West Monroe Street, Chicago, IL 60607

  • Open daily
  • Allow 2 hours

A unique and extraordinary experience awaits you at WNDR Museum, where you will discover interactive art installations that will spark your imagination and keep you entertained.

Visit an exhibit where you control music and lights with the push of a button and play around with an LED floor that follows your movements.

Additionally, take a selfie and be delighted as your photo is altered in 10 different ways with cartoon-like filters.

Tour digital works of art from around the globe, experience an infinity mirror room and view art inspired by 1960s comic books and imagery.

A tour of this museum will not only keep you engaged but also open your mind to possibilities and new forms of art.

34. Chicago Gangsters and Ghosts Tours

@Chicago Gangsters and Ghosts Tours

Rating: 4.9★

Entry Ticket: Adults: $35.00, Seniors: $25.00, Children: $17.00, Ages 6 and Under: Free

Address: 71 East W Wacker Drive, Chicago, IL 60601

  • Book in advance
  • Allow 2 hours

Famous for gangsters, such as the infamous Al Capone, Chicago is a great place to take a tour that caters to those interested in the history of the mob and even the spookier side of the city.

Want to find out more about Chicago’s notorious gangsters?

During your tour, your knowledgeable guide will regale you with not only the history of Chicago’s gangsters but details about their crimes, deals, and how they shaped the face of the city.

You will also be able to hear ghost stories as you make your way through the city, stopping at significant points of interest, such as Death Alley, Congress Hotel, and Palmer House.

Get a behind-the-scenes look at the history of Chicago’s gangsters, along with some of the old crime scenes that are now haunted locales.

Immerse yourself in the criminal side of Chicago while also getting some bone-chilling stories with Chicago Gangsters and Ghost Tours.

35. Chicago Cultural Center

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Rating: 4.7★

Entry Ticket: Free

Address: 78 East Washington Street, Chicago, IL 60602

  • Open Tuesday through Sunday, 10:00 am – 5:00 pm
  • Virtual and audio tours available
  • Allow 2 hours

Opened in 1897, the Chicago Cultural Center is now a landmark building in the city, where presidents, royalty, and diplomats have been welcomed to Chicago.

A popular destination for visitors to Chicago, the center hosts numerous exhibitions of visual, performing, and literary arts each year and is also the home of the Chicago Children’s Choir.

During your visit, you will be amazed at the spectacular architecture on display, from Doric columns and beautiful examples of marble from around the world to detailed mosaics and a large Tiffany glass dome.

Tour exhibitions that showcase the history of Chicago, race relations, nature, and gender equality, along with many other topics, through photography, painting, and art installations.

With so much to see and learn, the Chicago Cultural Center is one of the best things to do in Chicago. 

36. Christkindlmarket

Christkindlmarket, a traditional Christmas market held annually at Daley Plaza in Chicago, Illinois, United States. EQRoy | Shutterstock

Rating: 4.3★

Entry Ticket: Free

Address: 50 West Washington Street, Chicago, IL 60602

  • Open seasonally
  • Pet-friendly

If you’re spending time in Chicago during the Christmas holiday, you will want to visit Christkindlmarket, where you will be truly immersed in the magic of the season.

A German Christmas market, this yearly event provides diverse and numerous experiences for visitors.

Enticing smells of roasted nuts and hot spiced wine, along with festive music and dazzling Christmas decorations, will have you enchanted by the market.

With vendors offering tasty treats and warm drinks, you’ll want to take your time perusing the unique and charming booths that offer everything from handmade décor to clothing and artwork.

Be delighted by vibrantly painted nutcrackers and festive costumes as you take a look at Bavarian metal works, Black Forest clocks, and handblown Christmas ornaments.

A truly enchanting experience, you won’t want to miss out on this holiday event in Chicago.

37. Museum of Science and Industry

Thomas Barrat | Shutterstock

Rating: 4.7★

Entry Ticket: Adults: $21.95, Children: $12.95, Ages 2 and Under: Free

Address: 5700 South DuSable Lake Shore Drive, Chicago, IL 60637

  • Open daily, 9:30 am – 5:30 pm
  • Kid-friendly

Searching for something educational to do while in Chicago?

A trip to the Museum of Science and Industry is a unique delve into the world around us, with entertaining exhibits, meaningful collections, and fascinating displays.

View exhibits that showcase everything from architecture to flight.

Peruse displays where you will learn about the future of energy, genetics, and transportation.

Walk through an infinite maze of mirrors, interact with displays that get you up close to the science of nature, and view the only German submarine in the United States.

Enjoy a visit to this museum in Chicago, and you won’t be disappointed.

38. Navy Pier

Luis Enrique Torres | Shutterstock

Rating: 4.6★

Entry Ticket: Free

Address: 600 East Grand Avenue, Chicago, IL 60611

  • Open daily
  • Allow 3 hours
  • Pet-friendly

Navy Pier attracts nearly 9 million visitors a year with its numerous activities and attractions, from dining and shopping to events and views.

The 3,300-foot pier hugs the shoreline of Lake Michigan and boasts a classic Ferris wheel and carousel.

In addition, find public artwork, a children’s museum, a beer garden, and events that range from boat races to firework shows.

Shop the many vendors along the pier and discover clothing, novelty items, confectioners, and jewelry, along with much more.

Check out Navy Pier and enjoy a fantastic excursion that will keep you entertained while in Chicago.

39. The Chicago Theatre

F11photo | Shutterstock

Rating: 4.7★

Entry Ticket: Varies by show

Address: 175 North State Street, Chicago, IL 60601

  • Book in advance

Built in 1921, The Chicago Theatre hosts a variety of events, including stage plays, magic shows, and music concerts.

Covering nearly one-half of a city block, the theatre is enormous, with a six-story Paris-style motif, giving it not only an impressive presence but also making it charming and recognizable.

As you attend the theatre for a show or event, you’ll want to pay attention to the beautiful French architectural details of the historic building.

Be amazed by breathtaking gallery promenades, a grand staircase, and interior décor.

Relax during a night at the theatre, letting the ambiance of the building and elegance of the venue immerse you in an iconic Chicago location.

40. The Green Mill

Kristopher Kettner | Shutterstock

Rating: 4.5★

Entry Ticket: Varies according to show

Address: 4802 North Broadway, Chicago, IL 60640

  • Open daily, 4:00 pm – 1:00 am
  • Must be 21 or older

Are you ready for a fun night in Chicago?

Rich with the history of Chicago, The Green Mill is not only the oldest jazz club in the United States but was also patronized by the famous gangster Al Capone.

Built in 1907, the cocktail lounge still has the atmosphere of a speakeasy, with warm and intimate lighting, cozy corners, and classic décor.

Sip on a glass of wine as you sit back and relax, enjoy some of the best jazz music on offer in Chicago, and immerse yourself in the world of Al Capone and the history of the city.

If you have been to Chicago, what’s your favorite thing about it?