The Windy City, located inland in the Midwest, is competing to be named the top tourist destination in America. Each of the 57.6 million tourists visiting Chicago each year will find a suitable itinerary among the city’s many attractions.
You’ll be spoiled for choice regarding exciting things to do in Chicago. Art lovers, foodies, and history buffs may all rejoice since this huge Illinois metropolis has something to offer everyone.
Observe Lake Michigan’s gorgeous waters from a height of 1,000 feet or cruise across them in supreme luxury. Take a mob history class or a tour of Chicago’s renowned institutions. Eat some deep-dish pizza or have dinner at a restaurant with multiple Michelin stars. Start the day by indulging in some exquisite doughnuts, spend the afternoon discovering diverse neighborhoods or making new animal friends at the zoo, and finish the night with a nonstop party at one of the city’s renowned pub nightclubs.
No matter what you decide to do, you won’t be disappointed.
1. Things to do in Chicago: Soak in the skyline from a Lake Michigan sightseeing boat tour
Get off your feet for a moment; unwind on a boat as the skipper takes you around Lake Michigan, pointing out the famous sites and enlightening you on the city’s fascinating history. If you’re sick of the crowds, upgrade your experience by scheduling a private, luxurious sailboat trip or snagging a two-person pontoon.
Conversely, take a speedboat if you want some adrenaline with your tour. You will pass by some of the most recognizable locations in the city, including Grant Park and the Willis Tower, on these exciting, bright watercraft. It offers a fantastic fresh viewpoint on the city’s notable buildings and is fun.
2. Things to do in Chicago: Dare to explore the Medieval Torture Museum
Want to learn more about medieval torture in a fun way? In Chicago, there is a museum devoted solely to this.
Discover more than a hundred macabre pieces of equipment and gadgets from the most dreadful eras in human history. If you dare, observe numerous executions and painful methods used in a historical torture device.
Under-18s are not advised to visit the museum. No one without an adult will be allowed entry! Visitors can download a ghost-hunting app to find the ghosts of the tormented victims who still haunt the museum.
3. Things to do in Chicago: Visit Hogwarts with Harry Potter Magic Play
You will adore Harry Potter: Magic at Play if you still identify with your Hogwarts house! Fans of all ages may live out their magical fantasies in this fascinating interactive experience, which comprises three floors worth of enchanting regions.
There is no end to the adventures you will have, from potions class to the Quidditch field; you might even see some strange creatures in the Forbidden Forest! Grab your wand and join the party!
4. Things to do in Chicago: Explore the world of plants at the Chicago Botanic Garden
The Chicago Botanic Garden has much to offer visitors at any time of year. View the bright prairie, take in the brilliant blooms, and admire the meticulously maintained bonsai trees.
Additionally, many fantastic programs are available, including those on horticultural practices and topics like cooking, birdwatching, and photography. It’s one of the most tranquil things to do in Chicago, regardless of whether you’re crazy about plants or just like the environment.
5. Things to do in Chicago: Get a bird’s eye view on a helicopter tour
Keep your eyes on the skies for an unmatched view of the Windy City. Passengers may see the lovely city in all its glory during the day; at night, the skyline is illuminated from a different perspective.
As each local landmark is revealed, the pilot will identify it while revealing fascinating details about the city’s past and present.
6. Things to do in Chicago: Embrace your inner Homer Simpson on an original donut walking tour
Longtime fans of the doughnut include Chicagoans. With a focused desert tour that includes stops at some of the best doughnut shops in the Chicago Loop, you can sample the city’s best.
The tastes are free (but the hundreds you’ll want to take home aren’t), and vegan, gluten-free, and nut-free alternatives are available. This tour should be at the top of your list of things to do in Chicago if you have a sweet tooth.
7. Things to do in Chicago: Get Artsy At The Museum Of Contemporary Art
This well-known Chicago landmark has been greeting interested visitors since 1967, making it one of the largest contemporary art venues in the entire globe. Paintings, sculptures, photography, and film are all featured in the MCA’s constantly-changing displays, which are instructive and frequently participatory.
All year long, entrance is free for anyone under 18; in July and August, everyone is welcome. It provides a pleasant break from the sweltering summer sun even if you’re not an art fan.
8. Things to do in Chicago: Kindle some romance on a sunset sailing tour
On a twilight boat cruise, enjoy the magnificent sunset reflecting off the Chicago skyline while holding a glass of wine in one hand and your camera in the other.
A privately chartered sailboat offers the most romantic experience, while a large, shared vessel is more cost-effective.
9. Things to do in Chicago: Satisfy your palate on a food tour
Chicago may be known for its deep-dish pizza, but the Windy City also has a variety of other regional specialities. Indulge in Chicago-style hot dogs, dipped Italian beef sandwiches, a traditional deep-dish slice, and desserts of your choice for tea vendors, confectioners, and bakeries as you make a loop around the city on foot.
These excursions are hosted by locals and take you off the tourist trail, away from chain restaurants, and only inside the doors of well-known, genuine local eateries.
10. Things to do in Chicago: Step back in time on a prohibition tour
The Windy City has a long history of having connections to organized crime. Visitors will tour the city on a private bus with an entertaining tour guide costumed as a Chicago mobster, stopping at about 10 significant locations such as the Biograph Theater, Holy Name Cathedral, and the St. Valentine’s Day Massacre.
You will learn all the tales of the legendary mobsters that ran the town during Prohibition during the two-hour trip (1920s-1930s).
11. Things to do in Chicago: Eat and admire on the Spirit of Chicago dinner cruise
Combining a delectable all-you-can-eat buffet meal with stunning vistas of Lake Michigan will elevate the riverfront experience to a whole new level.
You will disembark feeling full and satisfied because the menu offers dinners, salads, and desserts. While the crewmates organize a few interactive games, a DJ will play music the entire time.
12. Things to do in Chicago: Challenge your mind at the Museum of Illusions
One moment you’re growing at a startling rate, the next, you’re joyfully stumbling down a winding hallway, and the next, you find yourself across the table from… yourself!
The wonders of the Museum of Illusions are absolutely endless.
You can visit more than 60 more mind-bending exhibitions besides the Vortex Tunnel, the Clone Table, and the shrinking and growing Ames Room. You serve as the tourist and the test subject in this unique environment!
13. Things to do in Chicago: Visit the vehicles at the Volo Auto Museum
The Volo Auto Museum is a must-see for all types of mechanical enthusiasts. Naturally, there are many cool cars to appreciate from the early 20th century to the present.
The museum has an extensive collection to show it, but it also honours mechanical victories of every kind. There are fascinating technologies everywhere, from motorcycles, singing robots, unusual musical instruments, and old steam engines.
Even a fleet of Batmobiles is visible!
14. Things to do in Chicago: Enjoy the scenery and greet the animals at Lincoln Park
Lincoln Park Zoo gained a reputation for excitement and prestige when it first opened in 1868.
The 35-acre facility is one of the oldest zoos in the nation (fourth-oldest, to be exact), and it is home to a wide variety of creatures, including amphibians, birds, mammals, reptiles, and more. Even though the park is in the middle of an urban jungle, it offers some amazing natural landscapes and magnificent animals.
North Avenue Beach is ideal for water sports, yoga, and swimming in warm weather.
And don’t forget to visit Lincoln Park Conservatory, where various ferns, palms, orchids, and other gorgeous plant species year-round create a tropical ambience. Wear comfortable shoes so the whole family can enjoy this amazing outing.
15. Things to do in Chicago: Listen to jazz or classical concerts at candlelight
Candlelight music and a distinct ambience are both lovely. You can listen to your favourite composers in a wonderful setting, including Louis Armstrong, Miles Davis, Mozart, and Tchaikovsky. Check out the current schedule.
16. Things to do in Chicago: Get some thrills at Six Flags Great America
Nothing beats a vacation to Six Flags Great America for those who are young at heart and love roller coasters!
One of the first wing coasters on the planet, the twisting, looping X Flight, will test your mettle. Or enjoy Aquaman Splashdown, a thrilling flume attraction with a 60-foot drop!
Additionally, younger guests might enjoy calmer rides like toy vehicles. A family-favourite park is created when live entertainment and themed seasonal experiences are added.
17. Things to do in Chicago: Spot constellations at the Adler Planetarium
The Adler Planetarium, which holds the distinction of being the first of its type in North America, offers a unique window into the astronomical and space sciences.
A vast array of artefacts is topped off by old telescopes, moon pebbles, a Gemini capsule, and even a section of the moon landing rover. In addition, the live stargazing shows and interactive exhibitions are unmatched.
The planetarium is located on the northeastern tip of Northerly Island, undoubtedly the best place to have a panoramic view of the city.
18. Things to do in Chicago: Learn about architecture at Frank Lloyd Wright’s Home and Studio
Frank Lloyd Wright is a gift to the city as a renowned American architectural genius who began his career there. He created over 1,000 buildings in his lifetime, many of which are still visible in Chicago today.
There is no better way to fully understand his accomplishments than to visit his Oak Park home and studio.
19. Things to do in Chicago: Spend an afternoon at Navy Pier
Famous restaurants, shopping possibilities, boat tours, and much more can be found at Navy Pier, a Chicago landmark on the lakefront.
The waterfront area was once intended to be just a freight dock. Still, it gradually changed over the past century to become the must-visit location it is today, complete with attractions, parks, and unparalleled views of the sparkling Lake Michigan.
Verse: The Art Of The Future, where you can use a VR headset and visit a virtual gallery, will appeal to art and technology aficionados. Get on the Centennial Wheel for commanding skyline views from 200 feet in the air for fantastic vistas of the outer world. The region, which also acts as the primary cruise departure point, is traversed by countless walking excursions. You may enjoy the Navy Pier attractions and 25 Chicago attractions and activities with the Explorer Pass.
20. Things to do in Chicago: Learn the true stories behind the city’s mob past
Embark on a focused gangster tour through the despised streets of Chicago to become fully immersed in the city’s illegal pleasures.
Explore historic crime locations, follow the footsteps of notorious criminals, and learn what motivated gangsters like Al Capone and John Dillinger. Combining it with a ghost tour can give you even more shivers!
21. Things to do in Chicago: Race against the clock at an escape room
If you manage to get away, you’ll have fun! The Escape Game is enjoyable for novices and professionals, thanks to the many rooms in every game, endless hints, and surprising “wow” moments around every corner.
Visit The Escape Game to select from 60 minutes of non-stop excitement with gold hunts, prison breaks, robbery riddles, and even rocketing to Mars.
22. Things to do in Chicago: See the real Chicago on a street art tour
Get off the beaten path with a special trip that avoids busy places and explores the underworld and backstreets. The largest city in Illinois is overflowing with urban art.
Guides not only show you some of the best murals in the city but also go through their histories and significance.
Choose one option that includes a stop at a craft brewery or allows you to BYOB if the thought of all that walking makes you a little thirsty.
Instagrammers, this should be at the top of your list when deciding what to do in Chicago!
23. Things to do in Chicago: Admire the vast collections at the Field Museum Of Natural History
This Chicago landmark, which boasts a collection of more than 40 million objects and is frequently hailed as one of the world’s finest natural history museums, draws millions of visitors annually.
The large museum offers interactive displays that examine more than 4.6 billion years of natural history. These include parts devoted to ancient Egypt, the Chinese Qing Dynasty, the dinosaur age, and other periods.
Children will enjoy sifting through the dinosaur bones at the Crown Family PlayLab. After your visit, stroll through the rest of the Museum Campus, a popular public area with many spots to relax and enjoy the view. Additionally, it is home to the magnificent Shedd Aquarium, making it the ideal Chicago attraction for science buffs.
24. Things to do in Chicago: Find serenity at the Garfield Park Conservatory
The world’s largest conservatory, dubbed “landscape art under glass” when it first appeared in 1908, also has a cutting-edge design. Landscape architect Jens Jensen regarded the Fern Room in particular, with its “prairie waterfall”—a stone and water feature inside a glass structure—as one of his greatest accomplishments.
The building has a haystack form and walls of layered stones. The 1.6 acres of the conservatory are home to some 120,000 plants representing 600 species. Four times a year, flower exhibitions are held to mark the changing of the seasons.
There is a requested donation at the entrance, but admission to the Garfield Park Conservatory is free and open daily throughout the year. Once inside, you can browse several rooms highlighting diverse plant species.
The Fern Room is crammed with lush ferns, the Aroid House is home to well-liked houseplants, and the Desert House is home to prickly succulents and cacti. In the summer, the outdoor gardens cover 12 acres of land and provide a multi-sensory experience that will transfer you somewhere else—even just for the day.
25. Tap your toes to late-night jazz at the Green Mill
In the 1920s, gangsters like Al Capone and others were hanged here, but it’s all about the music nowadays. Owner Dave Jemilo books sophisticated bebop and free jazz with a discriminating ear. He brought the club back to its former glory in the 1980s. Both perennial favourites Frank Catalano and Patricia Barber have regular appearances (Barber is here every Monday if she isn’t on tour). It’s generally understandably busy, so arrive early.
26. Make a pit stop at the Chicago Cultural Center
The Chicago Cultural Center has a variety of events every day, including free classical concerts, art exhibits in the many galleries, and visitors gazing in awe at the biggest Tiffany stained-glass dome in the world. Don’t worry about paying for entrance; almost all events in this building are free and accessible. The Chicago Cultural Center, located in a building as large as a full city block and built-in 1897 (when it first housed the Chicago Public Library), offers residents and visitors alike a chance to see incredible art and stunning architecture without spending a dime.
Visit Preston Bradley Hall in the Chicago Cultural Center to witness the 38-foot-diameter stained glass Tiffany dome, the building’s architectural highlight. The 30,000 individual glass panes that make up the dome were restored in 2008 so that the breathtaking show could once again be illuminated by natural light. If you want to do additional neck stretching, walk to the adjoining Grand Army of the Republic Hall, which has a neo-classical stained glass dome.
27. Grab a cocktail under glowing red lights at the California Clipper
We’re happy to report that most things are back to normal at the bar, from the same red leather booths flanking the walls to the same weekly live music. The glowing red lights at beloved Humboldt Park hangout California Clipper flickered back to life earlier this year after a pandemic-era closure thanks to an acquisition by the hospitality company Orbit Group (Good Measure, Signature). If you want a change of pace, head to the Clipper’s new rear room (formerly the location of the coffee shop C.C. Ferns) for DJ sets and late-night dancing that pays homage to Danny’s, the venerable Bucktown establishment that will close in 2020.
How to get to Chicago?
O’Hare and Midway are two excellent airports in Windy City.
Both offer a wide selection of local and international flights in addition to convenient access to the city. Additionally, the procedure can be made much simpler with an airport transfer!
Before leaving to explore neighbouring attractions like the shoreline of Lake Michigan and the artwork at the Art Institute of Chicago, you can dine in, work out, and even get a haircut at the Congress Plaza Hotel.
The Windy City has always been a favourite destination for tourists who want to experience urban living. And with more incredible attractions opening up every day, along with a fascinating, rich history, now is the ideal moment to go.
You can fill a lifetime with things to do in Chicago, whether into sports, the arts, cooking, or animals; therefore begin by making travel arrangements.
Read more from us: 29 Amazing Things to do in St Augustine