The Best Things to do in Chicago

The 15 Best Things to do in Chicago, Illinois

There’s so much to uncover about Chicago, Illinois. Originally established as a water transit hub, it emerged as a thriving metropolis, home to a vibrant arts scene, stunning architecture, and some of the best restaurants in the country.

By 1854, Chicago had become the world’s largest grain port, with a bustling population of 30,000 residents. But tragedy struck in 1871 when the Great Fire destroyed one-third of the city. Despite adversity, Chicago residents built back the city quickly and only grew it bigger. By the late 1800s, it was home to businesses of all industries and an ever-expanding skyline. It continues to grow today.

With so many things to see and do, it’s hard to know just where to begin your trip to Chicago. So we’ve compiled our list of the absolute best things to do in Chicago for you – from one-of-a-kind food tours to festivals celebrating its lively blues culture. 

Add these fun and unique activities to your Chicago bucket list, and there’s no doubt you’ll have an incredible time exploring the Windy City!

15 Fun and Unique Things to do in Chicago, IL

1. Eat at Taste of Chicago

Cool Things to do in Chicago: Taste of Chicago

Chicago is a foodie’s paradise, so it’s perhaps no surprise that the biggest food festival in the world is held in the Windy City. Taste of Chicago is one of the best things to do in Chicago if you love the idea of spending your vacation eating your way around the city. 

Held in Grant Park every July, this summertime tradition dates back to 1980. Each year, Chicagoans and visitors alike are invited to partake in five days of eating the best foods Chicago has to offer. 

Best Things to do in Chicago: Taste of Chicago

In addition to the lakefront festival in Grant Park, there are also pop-up events across Chicago neighborhoods throughout the five days. From cheesecake and pizza to ribs and shrimp, you’ll find classic Chicago treats, as well as more off-the-beaten-path foods.

But food isn’t the only attraction at this free-admission festival. Over near the Buckingham Fountain, you’ll find the Main Stage, where local, national, and international acts will be lighting up the night. There’s even more fun to be had with more events throughout the week, including dance lessons. So, grab a slice and get ready to boogie!


2. Attend the Chicago Blues Festival

Unique Things to do in Chicago: Chicago Blues Festival

Blues may not have begun in Chicago, but the city still has a long and rich history of celebrating this musical genre. In fact, there’s an entire genre of blues called Chicago blues that puts its own spin on what it means to sing the blues.

In early June, Chicago is home to the largest blues festival in the world. If you truly want to immerse yourself in Chicago culture, the Chicago Blues Festival is one of the coolest experiences you can have in the city. This three-day event features musicians from all over, both beloved favorites and up-and-coming talents. 

Previous performers include the likes of B.B. King and Etta James. The Chicago Blues Festival is free to attend and is held primarily in Millennium Park, as well as other venues throughout Chicago.

Blues not your thing? The Windy City also has a rich history of celebrating jazz, which is why the Chicago Jazz Festival is another one of the top things to do in Chicago. Also taking place in Millennium Park, with neighborhood concerts leading up to the main show, the Chicago Jazz Festival is another free event that showcases jazz talent from Chicago and beyond. It’s typically held throughout Labor Day weekend. 


3. Explore the Art Institute of Chicago

Fun Things to do in Chicago: Art Institute of Chicago

Located in Grant Park, the Art Institute of Chicago is one of the oldest and largest art museums in the world, making it one of the must-do things in Chicago if you’re an art lover. Open Thursday through Monday, this museum features both ongoing permanent installations and rotating exhibitions. From showcases of Salvador Dalί’s greatest works to explorations of life and the afterlife in ancient Egypt, this museum invites you to explore the world and its history through art.

The Art Institute of Chicago holds events every day, including daily tours given in both English and Spanish. Events also include talks and lectures from renowned art historians and professors that allow you to dive even deeper into the meaning of art.

Visitors are also invited to explore the museum’s Ryan Learning Center. Here you’ll find activities of all kinds, like doing unique art projects, making a custom museum tour with JourneyMaker, and more. The art activities are typically tied to the current exhibition, asking you to dive even further into an artist’s mind.

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4. Wander Around the Field Museum of Natural History

Best Things to do in Chicago: Field Museum of Natural History

As one of the largest natural history museums in the world, the Field Museum of Natural History is one of the best things to do in Chicago if you’re a history buff. With nearly 40 million specimens and artifacts in the museum’s collection, you could spend days here and still only see a fraction of what’s inside.

Stroll through the Rice Native Gardens to see over 100 species of native plants, discover the life of the Pawnee people of the Great Plains when you step inside a full-size replica of an earth lodge, observe how fossils get prepared, and so much more. The museum also includes additional ticketed events and exhibitions, like an immersive exhibit that shrinks you to smaller than a penny and invites you to take a closer look at what’s inside our soil!

Arguably the crown jewel of this museum is SUE, a 40-foot-long and 90-percent-complete T. rex fossil, making it the largest and most complete T. rex discovered. The museum helps SUE come back to life with the help of media experiences that recreate South Dakota 67 million years ago. With sensing stations, you can feel her skin, hear her roar, and even smell her breath.


5. Watch a Second City Comedy Show

Chicago has a vibrant comedy scene, with comedy clubs galore. But one of the most unique things to do in Chicago is to see a Second City show. The Second City is a legendary comedy school known for its incredible events and for creating comedy giants. 

Featuring both sketch and improv comedy, The Second City has shows happening every night. So, no matter when you visit, you can expect a hilarious night with these comedians. 

And who knows? You might just be watching the next big thing. Former Second City players include Alan Alda, Bill Murray, Gilda Radnor, John Candy, Eugene Levy, Catherine O’Hara, Tina Fey, Amy Poehler, Jordan Peele, Steve Carell, and Stephen Colbert. And that list truly only scratches the surface of the famous alums who once called The Second City home.


6. See Millennium Park and the Iconic Bean

Unique Things to do in Chicago: Millenium Park and the Iconic Bean

Located in the heart of Chicago, Millennium Park is a perfect spot for some Chicago sightseeing. There’s always something to do at this community hub. You’ll find concerts, festivals, and outdoor movie screenings here when the weather gets warm. And when it’s not so warm, you can skate around the McCormick Tribute Ice Rink!

Even when there aren’t special events happening, Millennium Park is a great way to spend an afternoon. Splash around the interactive Crown Fountain, go for a climb at Maggie Daley Park, or check out the art at the Boeing Galleries. For a peaceful space to relax, take a stroll through Lurie Garden, a 2.5-acre garden filled with color lined with a tranquil canal.

One of the most iconic Chicago attractions can be found in Millennium Park: the Cloud Gate, aka the Bean. This monumental structure is worth stopping by for a picture.

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7. Look Out from the Willis Tower

Fun Things to do in Chicago: Willis Tower

Previously called the Sears Tower, the Willis Tower held the record as the world’s tallest building for nearly 25 years. Although it no longer has that title, the 110-story, 1,451-foot skyscraper still offers one of the most incredible views of Chicago and perhaps the entire world.

The main attraction at the Willis Tower is the Skydeck. In addition to spectacular views, the Skydeck offers an interactive experience where you’ll uncover all of Chicago’s rich history. You’ll also get a simulated look at what it means to be 1,353 feet above some of the city’s biggest attractions, like Wrigley Field. 

Then it’s time to visit the Ledge. When you step out onto the Ledge, you’re actually stepping outside the Willis Tower’s 103rd floor. This glass box extends 4.3 feet out from the Skydeck at 1,353 feet in the air! It’s one of the coolest things to do in Chicago, as long as you’re not afraid of heights. 


8. Visit the Iconic Wrigley Field

Chicago Things to do: Wrigley Field

Wrigley Field, home of the Chicago Cubs, has been a symbol of Chicago since 1914, making it the oldest ballpark in the National League. It’s a historic site and a can’t-miss attraction.

The baseball season lasts from mid-spring to mid-fall, giving you plenty of time to see the Cubs in action. But even if you visit Chicago outside of those months, you can still see the iconic field. Wrigley Field offers 90-minute behind-the-scenes tours that invite you to learn all about the history of the ballpark while getting an up-close look at it. 

On game days, public tours will take you through the seating bowl, bleaches, upper deck, and field. But on non-game days, you get to see a bit more, with additional looks at the outfield ivy, press box, visiting clubhouse, and dugout.

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9. Stroll Navy Pier

Unique Things to do in Chicago: Navy Pier

A visit to Navy Pier has been one of the best things to do in Chicago since 1916. Stretching out into Lake Michigan, this 3,300-foot-long pier offers plenty to do for a full day of fun on your Chicago trip.

Head to Pier Park for tons of nostalgic fairground rides, as well as a very famous Ferris wheel. One of the biggest thrills on Navy Pier is the beloved Centennial Wheel. This nearly 200-foot-tall observation wheel invites you to soar into the sky for an incredible view of the city and beyond from a year-round, climate-controlled glass gondola.

At Navy Pier, you and your little ones can spend an adventurous day letting your imaginations run free at the Chicago Children’s Museum. Or you can spend the day out on the water for a boat cruise. At night, head to the Chicago Shakespeare Theater, where you’ll find world-class performances in one-of-a-kind shows.

From beer gardens to bakeries to BBQ joints, there are also several dining options. Definitely don’t miss visiting the Original Rainbow Cone, a classic Chicago treat with five flavors piled high in a cake cone. 

During the summer, Navy Pier hosts fireworks displays on Wednesdays and Saturdays. If you’re able to time it well, one of the best views to see the fireworks is from atop the Centennial Wheel. 

Throughout the summer, you’ll also find tons of events, from sunset yoga to artisan markets to concerts to movie screenings. If you’re visiting in the winter, you’ll be able to take part in Light Up the Lake, an incredible indoor lights experience offering fun for the whole family.

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10. Explore Garfield Park Conservatory

Chicago Bucket List: Garfield Park Conservatory

The 184-acre Garfield Park Conservatory is one of the largest greenhouse conservatories in the US and is known for its arrays of natural colors that make each garden look like a work of art. Stroll through 10 acres of outdoor gardens, see the stretching palms of the domed Palm House, walk around the indoor lagoon of the Fern Room, and so much more. 

Visiting here is both a peaceful way to spend an afternoon and a way to learn more about the natural world around us. From displays that teach us about how energy is created in plant life to exhibits that focus on how a plant could survive the driest regions on Earth, this conservatory is as beautiful as it is educational. 

Fun Things to do in Chicago: Garfield Park Conservatory

Little ones will love learning more about plant life in the Elizabeth Morse Genius Children’s Garden and the outdoor Play and Grow Garden. This conservatory, which is free to enter, is in high demand, so be sure to reserve your day here before your trip.


11. Take a Pizza Tour

Chicago Things to do: Chicago Pizza Tour

New York City isn’t the only place in the US that’s famous for its pizza. But if you think that the Chicago pizza scene is just filled with the same style of deep dish over and over again, you’d be sorely mistaken. Which is why going on a pizza tour is one of the most unique things to do in Chicago.

With Chicago Pizza Tours, your restaurant guide will take you through a variety of the best pizzerias to be found in the Windy City. You have three options for tours, but no matter which tour you take, you’re bound to have a fun, educational, and delicious time.

The Original Pizza Tour runs for 3.5 hours and invites you aboard a tour bus as you’re taken to visit four of the city’s best pizzerias. The Downtown Pizza Walk is a three-hour walking tour, where you’ll meet at Navy Pier before stopping by four happening downtown locations. 

The Bucktown Neighborhood Pizza Crawl is another walking tour, this time through the historic Bucktown neighborhood, where you’ll eat like a local at three sites. 


12. See the Animals at Lincoln Park Zoo

Best Things to do in Chicago: Lincoln Park Zoo

Having opened in 1868, the Lincoln Park Zoo is one of the oldest zoos in North America. It’s also one of only a few free-admission zoos, making it a no-brainer if you’re looking for free things to do in Chicago.

This 35-acre zoo brings you a look at wildlife in the heart of the city. The Lincoln Park Zoo is home to nearly 200 unique species and allows you to take a tour around the world and see what they look like in their natural habitats. See life at the farm at Farm-in-the-Zoo, watch the playful seals at Kovler Seal Pool, marvel at the monkeys at Helen Brach Primate House, and so much more.

In addition to animals, the zoo is alive with color thanks to more than 1,200 plant species. You’ll find many unique gardens, including the Charles Schwartz Memorial Garden and the Conservations & Science Gardens.

The Lincoln Park Zoo holds events all year round, from fundraising runs to craft beer festivals. But the biggest event comes at the end of the year when ZooLights returns. This annual winter event lights up the night with fun attractions for the whole family, including an illuminated maze, ice carvings, and a light show set to holiday music.

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13. Marvel at the Morton Arboretum

Chicago Bucket List: Morton Arboretum

Located in nearby Lisle, the Morton Arboretum is a public garden unlike any other. It’s truly one of the coolest things to do in the Chicago area, thanks to its stunning sculptures and natural landscapes. It’s a place of learning and a place of wonder!

Take on the challenge of the Maze Garden, find a moment of zen in the May T. Watts Reading Garden, or simply enjoy the beauty of the many tree-filled gardens, with everything from maples to willows. This arboretum also invites you to see it all from its many biking, skiing, and running trails. You can also hop aboard the Acorn Express for different tram tour options and adventures.

The Morton Arboretum also hosts many different exhibits, including Gateway to Science, where you’ll learn all about the arboretum’s research on tree science. You’ll also find new art exhibits being housed in the arboretum at all times, from colorful sculptures to wood carvings. 

Kids will love the four-acre Children’s Garden, which includes hands-on learning opportunities, tons of tree-themed play zones, and water features for added play during the summer months. And whether you’re traveling with young ones or just want to try some hands-on activities yourself, the arboretum has events happening every day that allow you to learn more about everything from gardening to beekeeping. 

One of the arboretum’s best events marks the end of every year. Illumination allows you to explore 50 acres of majestic trees as they’re lit up with color. Journey along a walking path as you listen to festive music and watch as the dazzling displays light up the night. 


14. See a Show at the Chicago Theatre

What to do in Chicago: Chicago Theatre

The Chicago Theatre is one of the most iconic Chicago attractions. It’s one of the most lavish and ornate theaters in the US and is a must-visit for any live theater lover. This French Baroque theater features intricate murals, a grand gilded staircase, and the famous six-story-high “Chicago” sign. 

To get an up-close look at the beloved theater, you can go on the Marquee Tour, which invites you to step back in time to 1921 and watch as the theater becomes one of the biggest and best entertainment venues in Chicago and beyond. 

Or you can get tickets to an event during your Chicago vacation. This theater has played host to the best in their fields, from jazz singers to comedians. Some acts who have graced the stage include Aretha Franklin, Dolly Parton, and Robin Williams.

See the Chicago Theatre


15. Study the Sky at the Adler Planetarium

Best Things to do in Chicago: Adler Planetarium

Founded in 1930, the Adler Planetarium was the first planetarium of its kind in the United States. Found on Northerly Island on Lake Michigan, visiting this planetarium is one of the best things to do in Chicago, especially if you’re a space and science fan.

Dedicated to inspiring the space explorers of tomorrow, this location includes several interactive exhibits. Astronomy in Culture allows you to see how cultures throughout time looked to the stars, while Mission Moon lets you feel what it’s like to be in charge of your own space voyage. 

And at the Doane Observatory, you can use the largest telescope in the Chicago area to observe the skies. These exhibits just scratch the surface of what’s available to you in this planetarium. 

A trip to the Adler Planetarium wouldn’t be complete without watching one of its famous Sky Shows. These Sky Shows take place under its iconic dome theater and allow you to get a front-row seat to observe the universe. 

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There you have it! The 15 best things to do in Chicago. What’s your favorite thing to do in Chicago?


Planning a trip to Chicago, Illinois? Check out our favorite books and travel guides!


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About the Author:

  • Jacqueline Gualtieri

    Jacqueline is a writer and editor pursuing the freelance life to explore the world. Born and raised in New Jersey, she spent her college years in Boston before settling down with her partner and puppy in Monterey, California.

    When she’s not writing, you can often find her planning her next trip. Road trips are her favorite, whether it’s driving across the country or simply exploring a new city in her own backyard. She loves uncovering the history of every new place she goes.

    Jacqueline has a restless passion for learning and makes it a goal to pick up a new skill every year. She’s picked up embroidery, crocheting, knitting, and cross-stitching, but she’s hoping to master more languages to help her in her travels. She’s also a published author, with short stories and poetry appearing in several anthologies.

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