45 Best Things to Do in Chicago That You Must Explore
What do you visualize when you think about Chicago? One of the most vivid impressions of the city is certainly a picture-perfect scene of magnificent architecture and an affluent urban ambiance along the riverfront. Chicago perfectly embodies both the famous past of the nation and the Modern American vision. The city offers everything you’d expect from a sizable metropolis, so if you’re wondering what the best things to do in Chicago are, look no further.
The Chicago itinerary includes world-class museums, exciting commercial areas, and a wide variety of nightlife options, to mention a few. Chicago is the cradle of modern skyscrapers. However, after you leave the city center, you’ll come across a completely different environment. It is a vibrant melting pot that is brimming with cutting-edge art projects and iconic landmarks.
We have rounded up the most fun things to do in Chicago for you to have an enjoyable vacation.
Top 45 Best Things to Do in Chicago
1. Enjoy a 360-degree Panorama of Chicago
What is It?
An observation platform called 360 Chicago offers a spectacular panoramic view of the city. It even has a bar where you can relax and sip drinks while taking in the scenery.
Why Go?
Being the birthplace of skyscrapers, it would be a magical experience to view the cityscape from a bird’s eye viewpoint. This is one of the best things to do in Chicago for adrenaline enthusiasts.
Don’t Miss
A platform composed of glass and steel called the TILT is available if you’re looking for yet more adventure. As implied by its name, the platform slants outward, forcing you to lean forward so you can look down and see the Magnificent Mile.
2. An Artsy Afternoon at the Art Institute of Chicago
What is It?
The Art Institute of Chicago is an art gallery featuring almost 300,000 pieces from around the globe in its archive.
Why Go?
The vast Art Institute of Chicago houses one of the nation’s most significant collections of impressionist and post-impressionist art. If you are an art enthusiast, it should be at the top of the list of things to do in Chicago this weekend. There are works from the Byzantine era as well as paintings that were finished recently.
Don’t Miss
The Art Institute also presents traveling exhibits that cover several topics and feature a wide range of artists and genres in addition to its permanent collection.
3. Experience the Urban life of Chicago from the Riverwalk
What is It?
You cannot probably miss out on the upbeat riverfront while listing out the best things to do in Chicago. The Riverwalk, as the name implies, is a pedestrian promenade that stretches along the Chicago River.
Why Go?
Given that it is 1.25 miles long, it doesn’t need strenuous activity. However, it is long enough to accommodate a variety of programs and festivals for all kinds of guests. Outdoor enthusiasts can hire a bike, or a kayak, or join a self-propelled boat excursion.
Don’t Miss
The promenade is transformed into an open-air gallery with a blend of temporary and permanent public art. A walk down the Riverwalk will unveil a plethora of pop-up art installations and live music.
4. A Vibrant Evening at Millennium Park
What is It?
The Millennium Park Campus is a public park in downtown Chicago. It hosts a variety of events, activities, and festivals, making it one of America’s most popular tourist destinations.
Why Go?
If you’re looking for the top things to do in Chicago, Millennium Park is unrivaled. Both locals and tourists congregate here year-round for a variety of activities, including picnicking on the grass, cooling down in the fountain, attending free concerts and film screenings, and much more.
Don’t Miss
You can’t go to Chicago without seeing the “Cloud Gate” or the bean-shaped metal sculpture that has come to characterize the city. Aside from the bean, you might explore its ice rink or a massive, video-playing water fountain.
5. Marvel at the Architecture of Willis Tower
What is It?
The Willis Tower, formerly known as the Sears Tower, stands 1,729 feet tall at its highest point. This skyscraper is often known as the crown jewel of the Chicago skyline.
Why Go?
You can admire the building from the ground as well as enjoy the spectacular view from the top. Enjoy amazing overhead views of buildings, busy pavements, lakes, bridges, and skies as you take in the miles-long horizon.
Don’t Miss
It features multiple observation decks for visitors in addition to being a busy commercial facility for broadcasting and radio. The Skydeck is a prominent platform with all-glass walls and flooring.
6. Experience the Past of the City in The Chicago History Museum
What is It?
The Chicago History Museum is the place you go to discover everything there is to know about the city.
Why Go?
The museum tour is one of the most fun things to do in Chicago due to its vibrant displays. The Chicago History Museum aspires to tell the tales of the city via carefully chosen programs, seminars, exhibitions, and other cultural treasures that engage visitors.
Don’t Miss
Dynamic animations, running trains, virtual fires, and children’s climbing scaffolds that resemble enormous Chicago-style hotdogs are just a few of the things that make history come alive.
7. The Iconic Centennial Wheel
What is It?
The Centennial Wheel is an iconic feature of the Chicago skyline. It is a giant metal wheel built by George Ferris Jr. in the 19th century for the World’s Fair in Chicago
Why Go?
The Centennial Wheel is now one of Chicago’s most renowned tourist destinations. It has been refurbished to include modern safety elements as well as all of the entertaining, high-class facilities. A ride on the Ferris wheel is ideal for a romantic night or a family adventure. You can also check chicago holiday destination.
Don’t Miss
You and your family will have the best time of your life while you view the city from the top of the Centennial wheel. For all the adventure buffs out there, this is probably among the most fun things to do in Chicago.
8. The Magnificent Mile
What is It?
The Magnificent Mile is a One-stop destination for all shopaholics out there. The Magnificent Mile in downtown Chicago has more than 450 retailers within walking distance.
Why Go?
This shopping street caters to more than just tourists and retailers. If you enjoy architecture, you will be captivated by the street’s diverse architecture. Aside from retail therapy, there are diversions such as Starbucks Roastery Reserve, the world’s biggest Starbucks.
Don’t Miss
As you stroll, look up to get views of the Chicago Water Tower, the longest-standing building on Michigan Avenue, and a survivor of the Great Chicago Fire of 1871.
9. A Leisurely Stroll at Grant Park
What is It?
Grant Park is a public space that covers about 313 acres and stretches from the eastern edge of the Loop to the northernmost reaches of the Near South Side. It is frequently referred to as “Chicago’s front yard.”
Why Go?
Grant Park’s carefully manicured lawns and spectacular vistas of downtown Chicago may appeal to you. This park is home to some of Chicago’s most prominent attractions, including the Field Museum and the Art Institute of Chicago.
Don’t Miss
Grant Park’s centerpiece, Buckingham Fountain is a multi-tiered water display. During 20-minute synchronized displays, it has 133 jets that blast water up to 150 feet into the air.
10. A Serene Stop at the Garfield Park Conservatory
What is It?
Garfield Park Conservatory is one of America’s largest botanical conservatories. This stunning glass building is home to over 100,000 plants.
Why Go?
If you are a nature lover, a tour around this greenhouse should be at the top of the list of the best things to do in Chicago. Indoors, guests may take advantage of the warm climate and lush vegetation. They can also explore more than 10 acres of gardens and children’s play areas in the natural world.
Don’t Miss
On the weekends, stop by Horticulture Hall for a lavender oat milk cold brew crafted by Monday Coffee Co.
11. Admire the Splendor of Chicago Cityscape from the Lake Michigan Sightseeing Boat Tour
What is It?
Skyline Lake Tours exclusively depart from our Navy Pier pier at 600 E. Grand Ave. You may elevate the experience by going on a luxury experience on your private sailboat or a two-person float.
Why Go?
You may see many of Chicago’s well-known buildings and the iconic skyline perspective on the boat trip, which makes a round around Lake Michigan and travels both north and south on the lake. If you’re tired of the crowds, this is a terrific method to get about the city.
Don’t Miss
You can learn about the history of Chicago’s buildings and how the city came to have such a famous skyline through these guided boat tours.
12. Chicago Culture Centre
What is It?
The Chicago Cultural Centre is the country’s first public municipal cultural facility, with a plethora of activities, installations, and architectural highlights.
Why Go?
While you are strolling along the loop, you should make a stop at this public facility. You will always stumble upon architectural expos and art installations by famous artists and designers.
Don’t Miss
As you enter the building, look up and marvel at the stunning Tiffany Glass dome. You may also visit the Landmark Gallery on the first floor to witness “The Great Chicago Fire in Focus,” an interactive exhibition featuring glass plate negatives of the Chicago Fire’s devastation.
13. An Elevated Trail
What is It?
Visit the abandoned stretch of an elevated railway track 606. The unique name is gained from the former three digits of the Chicago zip code.
Why Go?
If you wish to get to Logan Square, Humboldt Park, Bucktown, and Wicker Park, take this convenient path. The elevated trail stretching for about 2.7 miles is beautified by the locals and serves as an attraction point for tourists and locals.
Don’t Miss
Visit the colorful mural by Jeff Zimmermann that is situated across the Milwaukee Avenue bridge. The mural depicts the architectural legacy of Chicago.
14. Entering a Live Comic
What is It?
How fascinating is it to step into a comic? The Lakeview restaurant lets you feel as if you’re in a 2D comic world.
Why Go?
It is one of the fun things to do in Chicago that is sure to promise you various Instagram-worthy pictures. The black-and-white concept that started in Malaysia has reached Chicago.
Don’t Miss
Enhance your experience with the irresistible pon de ring mochi doughnuts.
15. Superdawg Drive-In Hot Dogs
What is It?
Wish to grab the yummiest hot dogs in town? Visit the drive-in with 40s essence that will serve you hot and yummy food in your car.
Why Go?
Eating at Superdawg could prove to be amongst the best things to do in Chicago with their yummy hit dogs served with several toppings and pickled green tomatoes.
Don’t Miss
Rather than taking super fries, try the superonionchips.
16. Saying Hi to Animals at Lincoln Park Zoo
What is It?
How amazing is it to experience the best things to do in Chicago and that too free of cost? Visit Lincoln Park Zoo which is a 35-acre land with a collection of animals from across the globe.
Why Go?
From birds to mammals to reptiles, there are different species of animals present in the zoo. This could prove to be one of the fun things to do in Chicago for all animal lovers.
Don’t Miss
Want to watch monkeys swinging from one branch to another? Visit the Regenstein Macaque Forest.
17. Chicago’s Only Aquarium– Shedd Aquarium
What is It?
Are you a nature fan? Visiting Shedd Aquarium can prove to be one of the best things to do in Chicago for you as it’s home to species of fish and aquatic creatures.
Why Go?
You can experience the Amazon and Wild Reef exhibition that’s always on display. With these exhibits, you can gaze at colorful fish, sharks, stingrays, and even an anaconda.
Don’t Miss
Say hello to the famous rockhopper penguins of the aquarium.
18. Gazing Tall Buildings from Promontory Point Skyline
What is It?
The best things to do in Chicago are mainly getting amused by the enticing skyline. Promontory Point is the best place to enjoy the view.
Why Go?
The man-made peninsula situated north of the Museum of Science and Industry is the best picnic spot that also lets you lounge and canoodle.
Don’t Miss
The Promontory Point is also a famous wedding destination that resembles the architecture of a miniature castle.
19. The Festive Lights
What is It?
Amongst the best things to do in Chicago is simply experiencing the festive vibes with glittering lights. Enjoy the special warmth and feel of the Christmas holiday season when in Chicago.
Why Go?
You’ll hum to the tunes of Christmas melodies since November 1 with 93.9 LITE FM and experience the lighting at Chicago Botanic Gardens. The experience is mesmerizing with early Christmas feels.
Don’t Miss
The marvelous light show arranged at Lincoln Park Zoo is one of the fun things to do in Chicago which shouldn’t be missed out on!
20. Discovering Frank Lloyd Wright’s Architecture
What is It?
One of the things to do in Chicago this weekend for architectural connoisseurs is to visit Frank Lloyd’s Robie House. It’s an existing definition of modern architecture, often referred to as ‘The cornerstone of modern architecture by the architect himself.
Why Go?
If you’re a fan of fine architecture, you ought to visit the Oak Park neighborhood to witness some of the exquisite marvels by Frank Lloyd Wright. The Robie House speaks a signature language for its designs and gives a peek into history with its interior decor.
Don’t Miss
Don’t neglect the aesthetics of an extremely beautiful art-glass window and the classic furniture nestling within the house.
21. The Historic Pullman Foundation Taking Back in Time
What is It?
It’s considered to be one of the fun things to do in Chicago as the Historic Pullman Foundation Exhibit Hall is home to Southern hood’s preservation and growth.
Why Go?
To understand the industrial revolution and how businessman George Pullman established the sleeping car factory, you need to visit the National monument.
Don’t Miss
Don’t miss out on the historic buildings placed within the district that have been featured in several movies like The Fugitive and Road to Perdition.
22. A Jazzy Night at Green Mill
What is It?
One of the fun things to do in Chicago is some free jazz to show your moves at the Green Mill.
Why Go?
The club is well-known to host one of the best live jazz nights. It was quite popular in the 1920s and welcomed several Chicago gangsters as well.
Don’t Miss
Don’t miss out on an Instagram-worthy click under the glittering marquee.
23. The Chinese Neighborhood of Chinatown
What is It?
Missing the Chinese vibes? Exploring Chinatown could prove to be one of the fun things to do in Chicago as you’ll experience the traditional cuisine, shops, and lovely sights built with East Asian architectural language.
Why Go?
To satisfy your taste buds, you can visit Chinatown for yummy food and a fun outing. Explore the different shops of the locality and gaze at the enticing skyline from the Ping Tom Memorial Park.
Don’t Miss
A cup of bubble tea from Joy Yee, satisfying dumplings from YX, and BBQ King House’s Peking duck is not to be missed when in the locality.
24. Home Music at Smart Bar
What is It?
Losing yourself to house music tops the things to do in Chicago this weekend. The special part? House music took birth in this city itself.
Why Go?
Chicago was the hub for new music melodies in the 1980s that continues to influence several electronic and hip-hop artists even today. Visit the Smart Bar to experience authentic music.
Don’t Miss
While you’re at the Smart Bar, attend the Queen dance party that happens almost every Sunday night.
25. An Artistic Walk on 16th Street
What is It?
Stroll through the artistic streets of 16th street and experience a collection of vibrant murals stretching along the Chicago River and extending to Western Avenue.
Why Go?
As you’re walking through the street, you’ll witness artworks by not only local artists but international and famed artists as well. A few of the artists featured on these walls are The Yok, Sheryo, Hebru Brantley, and JC Rivera.
Don’t Miss
This is one of the best things to do in Chicago for all artistic minds. As you visit this spot, do check out the infamous painting y ROA located at the 16th’s West and Laflin Street.
26. Kingston Mines and Live Blues
What is It?
Listen to live blues music. It’s one of the fun things to do in Chicago and Kingston Mines can make your experience even better.
Why Go?
One of the reasons this place is on the must-visit list is that it’s one of the oldest and largest blues clubs. You’re sure to be jazzed up by the energy of the bands that perform till 4 am on Thursdays and Fridays. The bands play till 5 in the morning on Saturdays.
Don’t Miss
One of the things to be aware of is that cover charges are for entry to the different stages and both the rooms of the club.
27. Touring Ludwig Mies Van Der Rohe Architecture at Illinois Institute of Technology
What is It?
One of the things to do in Chicago this weekend is to explore the architectural language set by Mies van der Rohe. the Bronzeville campus will take you back to the bright architectural era with several structures designed by a renowned German architect.
Why Go?
Mies van der Rohe is one of the iconic architects from American Modernism and you’ll witness a few of the most popular works on campus. He also serves as the director of the Architectural Department at the Armour Institute of Technology. You’re sure to be amused by the column-free structure of S.R. Crown Hall.
Don’t Miss
Seek a guided session offered by the Chicago Architecture Center to truly witness how the campus and overall designs evolved through time?
28. Biking to the North Branch Trail
What is It?
One of the best things to do in Chicago is the simple biking trail from Gompers Park that will lead the way to the Chicago Botanic Garden.
Why Go?
Are you looking for fun things to do in Chicago other than experiencing city life? Get ready with your bike and trail through the attractions of the northern suburbs. You can make a stop and have chilled beer at Hubbard’s Cabe or grab a pie from Pequod’s.
Don’t Miss
The Chicago Botanic Garden, trail through the four-mile loop passing through Skokie Lagoons.
29. The Real-Scale Lego at the Museum of Science and Industry
What is It?
Have you always been a Lego fan? Go and visit the exhibition named The Art of the Brick at the Museum of Science and Industry which nestles over 100 sculptures built with Lego.
Why Go?
Experience Da Vinci’s Mona Lisa, Michelangelo’s David, and a huge-scaled T.rex composed of tiny little lego blocks.
Don’t Miss
After touring through the different Lego sculptures, explore the ‘Take Flight’ exhibit featuring a part of a 727 plane where people can walk through it.
30. The Rock Club at Empty Bottles
What is It?
Visiting rock clubs can be one of the best things to do in Chicago. Witness the different rising bands at Empty Bottles.
Why Go?
The gigs at Empty Bottles give chance to local musicians and touring bands. You can experience experimental music, electronic acts, and rock bands. Grab a seat and enjoy the memorable musical melodies.
Don’t Miss
Move next door to the Pizza Friendly Pizza and have a slice before or after enjoying the show.
31. The Mind-blowing Chicago Magic Lounge
What is It?
Go and enjoy the most magical moment of your life in the Chicago Magic Lounge.
Why Go?
It’s one of the best things to do in Chicago as you not only get to enjoy the magic show but also amazing drinks and several performances.
Don’t Miss
As you’re sipping your favorite cocktail, check the magician’s table placed in the center of the bar.
32. 30 Plays within 60 Minutes
What is It?
Fun things to do in Chicago are all about several artists’ performances. Visit the theatre with the most popular art performance.
Why Go?
Attend Neo-Futurist’s signature show titled the Infinite Wrench which is extremely entertaining. The 2-minutes play let you enjoy a total of 30 performances in one hour.
Don’t Miss
Book the ffront-rowseats for an interactive experience with the artists.
33. The Second City Comedy
What is It?
Laugh your heart out as it is surely the best thing to do in Chicago or anywhere else. Enjoy the comedy shows by Chris Farley, Steve Carell, and Tina Fey at the Second City.
Why Go?
Before joining the Saturday Night Live cast, these comedians visited the stage to practice. You’ll enjoy the best comedy by the most talented artists.
Don’t Miss
Grab a seat and have fun at the two-hour-long comedy session titled Do the Right Thing, No Worries if Not.
34. Brew from Beer Temple
What is It?
Are you a beer fan? Enjoy the brews from Beer Temple and it could prove to be one of the best things to do in Chicago.
Why Go?
There’s always a surprise waiting for you at the bar.
Don’t Miss
The Instagram handle of Beer Temple has to be followed as you’ll know what’s in from their updates.
35. Carnitas Uruapan’s Famous Pork Tacos
What is It?
It’s a tiny Pilsen store that serves the best pig dishes.
Why Go?
Visit Carnitas Uruapan and decide the number of pounds you want to eat. The specialty is their juicy pork with corn tortillas that let you make your own tacos.
Don’t Miss
Although the restaurant offers a limited menu, enjoy the fresh and warm chicharrones.
36. Thin Crust at Vito and Nick’s Pizzeria
What is It?
The thin crust is served on your plate in the South Side Pizzeria.
Why Go?
The authentic Chicago’za pizza is one of the best dishes to enjoy here.
Don’t Miss
One of the best things to do in Chicago is try cuisines. Pair up the cracker-cut sausage pizza and an Old Style pitcher.
37. Chatter and Booze at Ale House
What is It?
When with your friends, one of the best things to do in Chicago is enjoy booze while listening to jazz jukebox and sharing stories.
Why Go?
Sip drinks with several cast of characters. This spot is famous for not only the tourists but cultural icons as well.
Don’t Miss
Don’t forget to gaze through the nudie paintings by Bruce Elliott.
38. California Clipper Cocktail
What is It?
Looking for things to do in Chicago this weekend? Grab your favorite cocktail at the California Clipper which is a famous bar that has again reopened after being closed for about two years.
Why Go?
The bar is famous for its glowing decor and the best cocktails.
Don’t Miss
Grab your cocktail at the Little Clip dance lounge which has the most fun DJ nights.
39. Alinea’s Best Meals
What is It?
Enjoy the best meals from a three-Michelin-starred Chef Grant Achatz.
Why Go?
Have fun with the best things to do in Chicago including a fine dining experience. You’re sure to enjoy the meals from Alinea’s tasting menu.
Don’t Miss
Along with the food, add a bottle of wine to the order from Alinea cellar.
40. Skylanding in Jackson Park
What is It?
Look at the amazing steel lotus petals by artist Yoko Ono in Jackson Park.
Why Go?
It’s one of the best things to do in Chicago for all art enthusiasts. These lotus petals attract several visitors to this 600-acre land.
Don’t Miss
Go through the traditional Japanese respite added to the park and dubbed for understanding.
41. Read at Pilsen Community Books
What is It?
Things to do in Chicago this weekend are soaking into the world of books. Browse through the bookstore of Pilsen.
Why Go?
It’s a way to support the local business while you read the books.
Don’t Miss
You can add some amount of donation to the Liberation Library.
42. Antiques and Oddities
What is It?
The best things to do in Chicago is to visit Woolly Mammoth Antiques and Oddities.
Why Go?
You can’t even expect what amazing stuff you’ll find at the antique store.
Don’t Miss
Check out the anatomy and medical stuff in the store.
43. Time for a Spin in the Maggie Daley Skating Ribbon
What is It?
Skating is one of the most fun things to do in Chicago. Grab your skate shoes and lap around the icy path of the traditional Maggie Daley Skating Rink.
Why Go?
The Ice Ribbon is a thrill to visit at the beginning of the winter. Along with the city’s chilly offerings, you also get to gaze at the skyline views of Chicago city.
Don’t Miss
Before planning your day for skating, make sure to book an online reservation, or else you might miss the spot in the crowd.
44. The Rainbow Cone Ice Cream
What is It?
The most fun things to do in Chicago are incomplete without yummy ice cream.
Why Go?
Satisfy the sweet tooth in the South shop that can easily be identified from afar by its bright pink color.
Don’t Miss
Try shakes, cakes, and sundaes as well from Rainbow.
45. Enter Ancient Egypt at the Field Museum
What is It?
If you’re a lover of historic collections, this can prove to be one of the best things to do in Chicago. The Field Museum nestles anthropological and biological collectives from the World’s Columbian Exposition.
Why Go?
The permanent exhibitions sprawled across 350,000 sq. ft of land enables several fun opportunities. You can explore Ancient Egypt which accommodates the recreation of Unis-Ankh’s tomb. You’ll also witness one of the ancient collections of mummies.
Don’t Miss
Explore the latest exhibit Death: Life’s Greatest Mystery and learn about the process of dying through several processes showcased.
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