Nestled inland in the MidWest, the Windy City is throwing its hat in the ring for the title of the premier American tourist destination. Chicago welcomes some 57.6 million tourists per year, and with such a diverse range of attractions, there’s an itinerary perfect for each and every one of them.
Art lovers, rejoice; foodies, celebrate; and history geeks, get excited – because there truly is something for everyone in this sprawling Illinois metropolis — you’ll be spoiled for choice when it comes to fun things to do in Chicago.
Admire the sparkling waters of Lake Michigan from 1000 feet high, or sail across them in divine luxury. Learn about the history of the mob or tour Chicago’s world-famous museums. Dig into a slice of deep-dish pizza or dine at multi-Michelin starred restaurants.
Start your day sampling some magnificent donuts, while away the afternoon exploring vibrant multicultural neighborhoods or meeting new animal friends at the zoo, and end the evening with a nonstop party at the city’s many renowned bars and nightclubs.
Whatever you choose to do, you won’t leave disappointed.
1 – Spend an afternoon at Navy Pier
Chicago’s iconic lakefront destination, Navy Pier plays host to renowned restaurants, shopping opportunities, boat tours, and so much more.
The waterfront space was conceived as merely a freight dock, however, its slowly evolved over the last century; today, the must-see destination features exhibits, rides, parks, and unbeatable views of the glistening Lake Michigan.
Art and tech fans will find plenty of common ground at Verse: The Art Of The Future, where you can don a VR headset and explore an entirely virtual gallery. And for great views of the real world outside, hop aboard the Centennial Wheel, which boasts commanding views of the skyline from 200 feet in the air.
Countless walking tours pass through the area, which also serves as the main cruise departure point. The Explorer Pass gives you access to the attractions at Navy Pier, plus other 25 attractions and activities in Chicago.
2 – Soak in the skyline from a Lake Michigan sightseeing boat tour
Get off your feet for a while; sit back and relax on a boat as the captain takes you around Lake Michigan, pointing out the iconic landmarks and delving into the city’s rich history along the way.
If you’re fed up with the crowds, take the experience to the next level by booking a private, luxury tour on your very own sailboat, or grab a two-person pontoon.
On the other hand, if you want a little bit of excitement with your tour, then head out on a speedboat! These fun, flashy watercraft will take you past some of the most iconic spots in town, including Grant Park and Willis Tower. It’s a great new perspective on the city’s famous architecture – and it’s tons of fun, too!
3 – Dare to explore the Medieval Torture Museum
Want to take a lighter look at the Medieval torture process? Chicago has a museum dedicated to just this.
Explore over a hundred gruesome tools and devices from the darkest times of human history. Witness multiple executions and pain-inducing techniques demonstrated with historic torture mechanism, if you dare.
The museum is not recommended under 18. No one will be admitted without an adult!
Visitors can download a ghost hunting app to detect spirits of the tortured victims which haunt the museum.
4 – See it all from the 360 Chicago Observation Deck
Located on the 94th floor of the John Hancock Center, the 360 Chicago Observation Deck offers spectacular views of the city’s crowded skyline (including the Willis Tower) and the shimmering lake Michigan below.
From the soaring 1,030-feet-high viewing platform, all four of the nearby states are visible (Illinois, Wisconsin, Indians, and Michigan).
Step outside onto the thrilling tilting platform (TILT), then unwind at the bar and soak in the sunset.
5 – Cheer for the home teams at the United Center
From the ice to the basketball court to the performance stage, United Center is a place of many facets. In terms of getting there, the Blue Line, which stretches through Downtown, drops you off within walking distance.
For hockey fanatics, it would be a sin to leave Chicago without watching the Blackhawks take on their competitors, while basketball enthusiasts can take in a Chicago Bulls game on the same hallowed ground where Michael Jordan once dominated the sport.
Even if you’ve never seen a match live, there’s no better place to watch the pros pass the puck than at the United Center, where the roar of a packed stadium is deafening. Outside of the sports seasons, there are tons of concerts and live events, so keep an eye on the calendar!
6 – Race against the clock at an escape room
You might escape… you will have fun! With multiple rooms per game, unlimited hints, and unexpected “wow” moments around every corner, The Escape Game is fun for everyone — beginners and experts alike.
Visit The Escape Game and choose from gold hunting, prison breaks, heist mysteries, even rocketing to Mars, all within 60 minutes of non-stop excitement.
Do you have what it takes to escape? Sign up for one of the most fun things to do in Chicago and find out!
7 – Learn the true stories behind the city’s mob past
Immerse yourself in Chicago’s criminal pastimes by embarking on a dedicated gangster tour through the city’s scorned streets.
Walk in the footsteps of infamous criminals, stand in historic crime scenes, and discover what made gangsters like Al Capone and John Dillinger tick.
Send some extra shivers down your spine by combining it with a ghost tour!
8 – Listen to jazz or classical concerts at candlelight
Enjoy a unique atmosphere at candlelight while listening to wonderful music
From Louis Armstrong to Miles Davis, from Mozart to Tchaikovsky, there is plenty of choices to listen to your favorite composers in a magical environment. Take a look at the current program.
9 – Take an architecture cruise on the Chicago River
The architecture in the Windy City is unique, historic, and complex, and there’s no better vantage point to admire it all than the waters of the Chicago River. As you cruise under the city’s skyscrapers, you’ll pass the East Bank Club, the old Post Office Building, the Willis Tower, and plenty more.
Highlights include the DuSable Bridge, with its decorative posts and impressive engineering; Tribune Tower, a magnificent Neo-Gothic luxury apartment complex; and the Wrigley Building, a classic skyscraper that serves as a focal point for public life in the Windy City.
You can also take a cruise with the Chicago Architectural Center, which celebrates the town’s magnificent designs and historic structures. After visiting the exhibits, you can join one of their tours and admire the buildings in the best possible way – on the water!
Tours typically last an hour and a half, and the guides are notably informative and entertaining.
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Step into a Century of Magic with Disney100!
Put on those mouse ears and start your magical journey with the Disney100: Exhibition in Chicago! Immerse yourself in a century of Disney stories, from the classic Snow White to the recent Encanto. Marvel at rare artifacts, costumes, and treasures from Pixar Studios and the iconic Star Wars films among others.
10 – Explore the world of plants at the Chicago Botanic Garden
No matter what time of year you visit, the Chicago Botanic Garden has plenty to offer. Check out colorful blooms, admire the carefully cultivated bonsai trees, and gaze out over a small but vibrant prairie.
There are also tons of awesome classes covering everything from cooking to birdwatching to photography – and horticultural techniques, of course!
Whether you’re plant-obsessed or just enjoy the scenery, it’s one of the most relaxing things to do in Chicago.
11 – Explore the Lakefront on a segway tour
As the third-largest city by population across the entire country, Chicago is unquestionably massive. That means seeing everything on foot is next to impossible. Why not speed things up and tick off a few more attractions by joining a Segway tour?
Glide through downtown, the riverfront, or a number of other routes on offer, all while learning about the city from a seasoned local. These smooth-moving machines are fun for the whole family.
Hot tip: Discover fun & unusual things to do in Downtown Chicago
12 – Get a bird’s eye view on a helicopter tour
Take to the skies for an unrivaled perspective of the Windy City. By day, passengers can see the picturesque city in full force; by night, the skyline illuminates for a completely different view.
The pilot will point out all of the city’s icons as they come into view, while also providing fascinating insights into the history and culture of the city.
Read our latest article about helicopter tours in Chicago.
13 – Embrace your inner Homer Simpson on an original donut walking tour
Chicagoans have long adored the donut. Taste the very best the city has to offer with a dedicated desert tour, stopping into a hand-picked selection of the Chicago Loop’s top donut shops.
The tastings are all included (though the take-home dozens you’ll be craving aren’t), while vegan, gluten-free, and nut-free options are also available.
For anyone with a sweet tooth, this tour should headline your bucket list of things to do in Chicago.
14 – Ride through the town on a bike tour
Burn off the deep-dish pizza from the night before and explore the city at a much faster pace by opting for a bike tour.
While the lakefront trail comes highly recommended as a city staple, a number of adventurous and themed options are available too – like horror-focused and pizza-focused cycle tours!
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A Journey Through Time – Titanic: The Exhibition!
Imagine stepping back in time and reliving the glory days of the Titanic… Get an authentic boarding pass, explore carefully recreated environments, and take the opportunity to admire over 300 historical artifacts in this immersive exhibition. Take a journey into the past as the history of the world’s most famous ship is brought to life.
15 – Experience the magic of molecular mixology at The Cauldron Chicago
Want to brew up some magical elixirs and step into the world of your childhood fantasies? Get ready for a magical experience like no other at The Cauldron Chicago!
Using your very own magic wand, you’ll cast spells to pour your welcome drink straight from the maw of a mystical creature.
Then, at your own magic station, brew up two molecular cocktails with different effects to choose from. The Interactive Potions List changes with the seasons, so there’s always something new to discover!
16 – Admire the specimens at the Shedd Aquarium
From the shallow tidepools to the depths of the sea, Shedd Aquarium offers the full scope of the ocean – right in the heart of the city!
Enjoy the antics of playful beluga whales, admire the vivid colors of tropical fish and their coral reef habitats, or observe the fascinating behavior of the enigmatic Giant Pacific Octopus.
You can also see several other species that live in water-adjacent ecosystems, from alligators to frogs to penguins. Stop by and dive in for some wonder!
17 – Tour the Chicago River by kayak
In either a solo or tandem kayak, soak in the famous skyline views with a peaceful paddle along the Chicago River.
All the equipment is included with the tour, likewise the knowledgable guide who’ll spill architectural, cultural, and historical tidbits throughout the journey.
For something a little more spooky, glide down the river by moonlight on a ghost-themed outing.
18 – See the real Chicago on a street art tour
Illinois’ largest city is teeming with urban art; get off the beaten track with a unique tour that steps away from the crowded sites and explores the underground and the backstreets instead.
Guides not only take you to some of the city’s premier murals but also explain their meanings and histories.
If the idea of all that walking makes you a little thirsty, choose one of the options which stop into a craft brewery or allow you to BYOB.
Instagrammers, this should be a priority when it comes to choosing between all the things to do in Chicago!
19 – Feel the thrills of indoor skydiving
If you’ve always dreamed of skydiving but could never muster up the courage to freefall from a plane, iFLY Chicago has the perfect solution.
Nestled in Chicago-Lincoln Park, this adrenaline-pumping activity delivers that wind-in-your-face feeling without all the nerves.
It’s significantly cheaper than traditional skydiving, and the ideal stepping stone to the real thing.
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Enchanting Nights: The AirOtic Soirée Experience
Dive into the electric atmosphere of “AirOtic Soirée,” an unforgettable burlesque cirque cabaret that combines acrobatics and the allure of sensuality. Savor delicious cocktails as you’re drawn into a world where elite acrobats perform breathtaking feats of athleticism, each move a testament to the art of desire. This one-of-a-kind event promises a blend of spectacle and intimacy, setting your senses alight in an atmosphere charged with seduction.
20 – Admire the vast collections at the Field Museum Of Natural History
Regularly spoken of as one of the world’s greatest natural history museums thanks to its collection of over 40 million artifacts, this Chicago icon welcomes millions of tourists year after year.
The enormous museum features immersive exhibits that explore over 4.6 billion years of natural history, including dedicated sections to ancient Egypt, the Chinese Qing Dynasty, the dinosaur era, and beyond.
Youngsters are sure to love digging up the dinosaur bones at the Crown Family PlayLab.
After your visit, take some time to explore the rest of the Museum Campus, a beloved public space with plenty of places to sit, stroll, and enjoy the scenery. It’s also home to the spectacular Shedd Aquarium, offering a perfect double-header for science geeks looking for things to do in Chicago.
21 – Get some thrills at Six Flags Great America
For the young and young at heart (and rollercoaster enthusiasts), there’s nothing like a trip to Six Flags Great America!
Test your mettle on X Flight, a twisting, looping adventure that’s one of the first wing coasters on the planet. Or catch the spray at Aquaman Splashdown, a lively flume ride with a 60 foot plunge!
And littler visitors can try out mellower rides like the miniature cars. Throw in live entertainment and themed seasonal experiences, and you have a park that’s a surefire family favorite!
22 – Get artsy at the Art Institute of Chicago
Found in the hustle and bustle of Millennium Park, step inside the second-largest museum in all of North America (behind only NYC’s Met).
Boasting a collection exceeding 260,000 artifacts spanning Post-Impressionist paintings to experimental photography and everything in between, it’s no wonder that the Art Institute of Chicago is rated as TripAdvisor’s top attraction.
For a contradictory approach to art (and the opportunity to break the regular rules and eat in the museum), check out the ‘Un-Highlights’ tour.
23 – Get Even Artsier At The Museum Of Contemporary Art
Easily one of the world’s largest contemporary art venues, this popular Chicago attraction has been welcoming curious guests since 1967.
The MCA‘s ever-changing exhibits span paintings, sculptures, photography, and film, all educational and often interactive.
Under-18s get in free year-round; in July and August, admission is free for everyone. Even if you’re not an art fan, during the scorching summer months, it’s a welcome respite from the beating sun.
24 – Indulge in a one-of-a-kind dining experience at Chicago’s 2D Restaurant
Every corner of the uniquely hand-painted 2D Restaurant transports you to the pages of a comic book and offers unique and unforgettable photo opportunities to make your dining experience even more captivating.
From irresistibly sweet Japanese mochi donuts and smooth Vietnamese coffee to richly flavored Taiwanese fried chicken sandwiches, enjoy a wide range of trendy Asian gourmet treats.
Recently ranked among the top 20 donut shops in Chicago, the 2D Restaurant has quickly become a must-visit restaurant in the city. Whether you’re a foodie or a fan of unique interiors, this charming black-and-white cartoon world promises an unforgettable trip.
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Sip and paint in the dark at this unique workshop!
This retro-futuristic experience combines the thrill of painting with a fluorescent twist, offering a brush in one hand and a choice of drink in the other. The musical backdrop adds to the atmosphere, making it a perfect outing for friends. By the end of the night, not only will you have had an unforgettable experience, but you’ll also leave with a personal masterpiece to proudly display at home.
25 – Spot constellations at the Adler Planetarium
Boasting the title of the first of its kind in North America, the Adler Planetarium is an unrivaled insight into the worlds of space and astronomy.
Old telescopes, moon rocks, a Gemini Capsule, and even a section on the moon landing rover cap off an extensive list of artifacts. Likewise, the interactive exhibits and live stargazing shows are second to none.
The planetarium sits on the northeast tip of Northerly Island, a location that offers arguably the best land-based panoramic view of the city’s skyline.
26 – Take A Selfie At Cloud Gate (AKA The Bean)
We’ve all seen it pop up on our social media feeds; a selfie in front of the Bean (which, technically, is called ‘Could Gate’) is a right of passage for any Chicago tourist.
A quick social media most here one of the most popular things to do in Chicago, no doubt.
The giant bean-shaped mirror weighs 110 tons and sits in Millennium Park, the popular lakefront area in Chicago’s downtown Loop.
27 – Kindle some romance on a sunset sailing tour
With a glass of wine in one hand and your camera in the other, soak in the glorious sunset as it reflects off the Chicago skyline on a twilight boat tour.
Choose from a budget-friendly option on a large, shared vessel, or splurge on the ultimate romantic experience with a privately chartered sailboat.
28 – Stand above Chicago at the Willis Tower Skydeck
Take the lightning-quick elevator up to the 103rd floor of the former Sears Tower for views that arguably overshadow those even of the John Hancock Center.
While you won’t be able to see the Willis Tower (since you’ll be standing in it), the scenes are truly remarkable.
Acrophobics, look away now; the Skydeck’s Ledge features four glass cube enclosures that jut out into the thin air. They make for amazing photo opportunities and get the adrenaline pumping.
Read more about Chicago Skydeck tickets.
29 – Satisfy your palate on a food tour
Chicago might be renowned for its deep-dish pizza, but the Windy City actually boasts a number of local delicacies.
Try them all as you loop around the city on foot, devouring Chicago-style hot dogs, dipped Italian beef sandwiches, a classic deep-dish slice, and treats of your choice for tea merchants, confectioners, and bakeries.
These locally-led tours take you off the beaten track and away from the tourist traps and chain restaurants; you’ll be guided exclusively through the doors of beloved and authentic local eateries.
30 – Let your imagination run wild at the LEGOLAND Discovery Center
No matter if you’ve just turned 5 or 50, everyone loves Lego! The large complex offers Lego-themed rides, building sections, a 4D cinema to delight the senses, and a gift shop to buy all the Lego sets you could possibly fit in your suitcase.
The Discovery Center is situated outside of the main Chicago area, so make a day trip out of it and explore the adjacent Ned Brown Preserve (Busse Woods) while you’re there.
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The Drunk Shakespeare Society: where cocktails and classics meet
Mix cocktails and classics for an unforgettable evening at the Drunk Shakespeare Society. A hidden gem behind the Chicago Theater, sets the stage for five fearless actors. While sipping on a variety of alcoholic beverages, the Shakespearean show will be played in a funny way, creating a unique way every time.
31 – Learn about architecture at Frank Lloyd Wright’s Home and Studio
As a noted visionary of American architecture who started his career in Chicago, Frank Lloyd Wright is a treasure to the city.
He designed more than 1,000 structures in his lifetime, many of which still stand in Chicago to this day.
There’s no better way to get an in-depth view of his achievements than by touring his home and studio in Oak Park.
32 – Catch a show at the Chicago Theatre
Besides sitting down for a show at the world-famous Chicago Theatre, visitors are blessed with the opportunity to go behind the scenes and explore the grand history and intricate architecture of this iconic entertainment venue.
Step on stage, visit the rehearsal space, admire the ceilings, and more, all with an expert guide leading the way.
The theatre is centrally located to countless bars and restaurants, which makes planning the evening outing a breeze.
Hot tip: Immerse yourself in the vibrant theater scene, where attending a Broadway show or a local theater production ranks as one of the best indoor activities in Chicago.
33 – Step back in time on a prohibition tour
The Windy City has always been known for its ties to the mob.
With a lively guide dressed as a Chicago gangster, visitors will zoom around town on a private bus, stopping into around 10 relevant sites like the Biograph Theater, Holy Name Cathedral, and St. Valentine’s Day Massacre.
Throughout the two-hour tour, you’ll hear all the stories of the decorated mobsters that ruled the town in the Prohibition Era (1920s-1930s).
34 – Devour a delicious brunch on the Chicago Odyssey Cruise
Captivating views of the Chicago skyscrapers are aplenty on board the luxurious Chicago Odyssey.
On a typical 2-hour cruise, guests have access to a fresh brunch buffet, offering the best of the breakfast and the lunch menu, and complemented by a gourmet coffee bar.
Cap off the journey with a mouth-watering mimosa before disembarking at the 3,300-foot-long Navy Pier.
35 – Roll out on some bus tours
Whether you’re a morning bird or a night owl, there’s a perfect bus tour for you! Spend the day rolling past icons like the John Hancock Center, Millennium Park, and Navy Pier, while an audio guide recounts the city’s fascinating history.
In the evening, hop aboard a night bus, and see the same sights lit up in their dazzling finery. And if any of the sights catch your eye, you can always disembark, explore, and get back on the next vehicle when it arrives.
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Discover the future of art
“Art of the Future” is a groundbreaking exhibition at Block 37 in Chicago that blends art and technology to create an immersive experience in the world of digital art and augmented reality (AR). This exhibition invites visitors to step into the metaverse and explore augmented reality holograms and artworks by leading artists in the digital sphere, revealing the future of art.
36 – Let the kids run wild at the Chicago Children’s Museum
Located at Navy Pier, the Chicago Children’s Museum is regularly considered the premier kids’ museum nationwide.
The immersive attraction features a plethora of hands-on exhibits that the youngsters absolutely love – perhaps none more so than the Dinosaur Expedition, where they can dig for bones and pretend to be archaeologists.
37 – Wet your whistle on the Barrel Run
With a thriving craft beer scene that’s only advancing with every passing year, it would be a sin to visit the Windy City without sampling a few local brews.
But this isn’t your average barhopping walking tour; thirsty travelers whiz around town in the one-of-a-kind Barrel Bus, sampling plenty of cold beer from start to finish.
38 – Tour the Frederick C. Robie House
A UNESCO World Heritage Site, the prairie-style Frederick C. Robie House – designed by none other than Frank Lloyd Wright – is considered a pivotal stepping stone in the advancement of American architecture.
Tours run Thursday through Monday and include a stroll through the house and the gardens, led by an expert guide.
39 – Eat and admire on the Spirit of Chicago dinner cruise
Take the riverfront experience to the next level by combining pristine Lake Michigan views with a delicious all-you-can-eat buffet dinner.
The menu includes entrees, salads, and desserts, ensuring that you disembark entirely stuffed and satisfied.
A DJ will spin the tunes all the way through, while the crewmates coordinate a few interactive games.
40 – Obsess Over Famous Wordsmiths At The American Writers Museum
With an abundance of interactive displays detailing all facets of the nation’s literary history, the American Writers Museum in the heart of Downtown is a bookworm’s delight, and one of the most unique things to do in Chicago.
In addition to blurbs about tens of revolutionary wordsmiths, the museum also displays artifacts like typewriters, hand-written notes, and old-school quills.
41 – Feed yourself at the Taste of Chicago Festival
Foodies, it’s time to get excited! Hosted in Grant Park, Taste of Chicago is considered the world’s largest food festival – and best of all, the 5-day event is free of charge.
If you happen to be visiting in July, don’t miss the chance to sample some of the tastiest treats that the city can muster up.
Even if you’re not hungry, the atmosphere and live music are still worth checking out.
42 – Challenge your mind at the Museum of Illusions
One minute, you’re changing size at an alarming rate; the next, you’re happily stumbling your way through a twisting hallway; and moments later, you’re sitting across the table from… yourself!
At the Museum of Illusions, the wonders truly never end. Along with the Vortex Tunnel, the Clone Table, and the shrinking and growing Ames Room, you can explore more than 60 other mind-bending exhibits.
In this fascinating space, you’re both the visitor and the test subject!
43 – Board the iconic tall ship Windy
Modeled after a traditional Great Lakes trading ship, the Tall Ship Windy is as charming as it is historic.
The majestic 148-foot schooner sets sail from Navy Pier out to the calm waters of Lake Michigan, where spectacular views of the Chicago skyline await.
The trip isn’t only picturesque, but interactive as well – guests assist in raising the sails and sending out the commands to the crew.
44 – Make sightseeing competitive with a scavenger hunt
With limitless attractions scattered across the city, walking around from A to B can get a little repetitive. Why not spice it up a bit with a little extra adventure?
The professionally-orchestrated Scavenger Hunt games combine sightseeing with interactivity, sending players all over the city to solve puzzles and complete tasks, Amazing Race-style.
Sign up for a city-wide adventure, or get specific with a hunt centralized to the Magnificent Mile or the Chicago Zoo.
45 – Learn about the city’s past at the Chicago History Museum
On the southernmost point of the sprawling Lincoln Park, the Chicago History Museum showcases millions of artifacts dedicated to the stories of the city’s past.
Its eye-opening exhibitions dive into Chicago’s multiculturalism, its history with democracy and women’s activism, the Civil Rights movement, and so much more.
Visit on a Tuesday to score free entry!
46 – Head to the Ernest Hemingway Birthplace Museum
Arguably the most famous American author of all time, the Ernest Hemingway name has since echoed across the globe.
He was born, of course, in Chicago, and keen visitors are welcome to explore the childhood home-turned-museum in which he lived at the turn of the 20th century.
Tours through the museum dive into the life, work, and legacy of the Pulitzer Prize-winning author – a must for any literary fan.
47 – Visit the vehicles at the Volo Auto Museum
For machine fans of every stripe, the Volo Auto Museum is a must-see. Of course, there are plenty of cool cars to admire, from the early 20th century to the present.
But the institution also celebrates mechanical triumphs of every type, and has an impressively broad collection to prove it!
From motorcycles to singing robots, unique musical machines to antique steam engines, there are intriguing devices around every corner.
You can even see a fleet of Batmobiles!
48 – Enjoy the scenery and greet the animals at Lincoln Park
Since its opening in 1868, Lincoln Park Zoo has developed a reputation for excitement and prestige.
One of the most established zoos in the country (fourth-oldest, to be exact), the 35-acre complex houses animals of all shapes, sizes, colors, and origins – amphibians, birds, mammals, reptiles, and more.
As if the awesome animals weren’t enough, the park offers some fantastic natural scenery in the heart of the urban jungle. During warm weather, North Avenue Beach is perfect for swimming, watersports, and yoga sessions.
And don’t miss Lincoln Park Conservatory, where numerous species of ferns, palms, orchids, and other stunning plants cultivate a tropical atmosphere all year round.
It’s a fantastic excursion for the whole family – just remember to wear comfortable shoes.
49 – Dance the night away clubbing
Hundreds of bars and clubs line the city streets, so choosing a destination isn’t always easy – but, to be honest, it’s hard to go wrong!
Gawk at world-famous DJs at the long-standing Smartbar, a frantic mix of house and electro beats; head to The Underground, a high-profile club frequented by celebrities; or drink with sophistication at the Green Mill Cocktail Lounge, a far more relaxed and subtle night.
No matter where you end up, the Chicago nightlife is destined to impress.
50 – Watch a film beneath the stars with Rooftop Cinema Club
When the weather is warm, there’s no better place to be than on a rooftop overlooking the Chicago skyline. What makes it even better is if there’s a movie you can watch beneath the evening stars!
With the Rooftop Cinema Club, you can indulge in not only a cracking film, but in delicious snacks and drinks too. Lounge in comfortable chairs with your friends and family, or grab a loveseat with your partner. Located atop The Emily Hotel, here you can also enjoy the hotel’s full food menu and bar.
51 – Rent a private luxury boat (with pizza included!)
Deep-dish pizza is an undisputed Windy City icon. Why not kill two birds with one stone on a luxury boat tour that includes its own pie?
On this private pontoon, suitable for 2-6 people, you’ll glide past Goose Island, the Riverwalk, Willis Tower, the Civic Opera House, and plenty more; staying far away from the selfie-stick-wielding crowds of tourists.
52 – Party it up at some festivals
In a town like Chicago, there’s always a party to be found. But when the weather gets warm, the city really comes alive!
Check out hundreds of top-notch performers at the Chicago Jazz Festival during Labor Day weekend. Stop by in late July or early August for Lollapalooza, a world-renowned showcase for current headlining acts.
Or savor the Millennium Park Summer Series, a range of concerts featuring everything from country music to orchestral productions.
These festivals are a perfect seasonal treat!
53 – Visit the DuSable Museum of African American History
As a genuine cultural melting pot, Chicago presents as the perfect city to dive into the history of African American culture.
Through concerts, films, exhibitions, and events, the DuSable Museum of African American History has been educating its guests about the journeys of Africans and African-Americans for more than 50 years.
It’s a fascinating learning experience immersed within the greenery of Washington Park – a welcomed breath of fresh air compared to Downtown.
54 – Walk with butterflies at the Peggy Notebaert Nature Museum
Surrounded by the well-kept lawns of Lincoln Park, the Peggy Notebaert Nature Museum is a great indoor venue to visit before or after a stroll through the sprawling park.
The museum houses a beautiful aviary collection, and the ever-popular Judy Istock Butterfly Haven, in which over 1,000 butterflies flutter by. Those brave enough can even hold a live snake!
55 – Learn about Latin culture at the National Museum Of Mexican Art
Nestled within Chicago’s Pilsen neighborhood, this free museum provides an exciting, educational insight into Mexican and Latin American culture.
With a collection covering some 9,000 pieces of art spanning from ancient Mexico to present modern times, the National Museum of Mexican Art proudly showcases one of the country’s largest Mexican art collections.
56 – Witness the wonderful weirdness of the Blue Man Show
You’ve seen their famously painted faces… now get ready for their show! Since 1987, the Blue Man Group has been sharing their show with the world – a truly unique performance!
Lose yourself in a world of color, music, and wild creativity, guided by the iconic men themselves. Slyly funny and constantly innovative, this feast for the mind and the senses will keep you on the edge of your seat.
57 – Unleash the youngsters at Pirates’ Cove Children’s Theme Park
Specifically designed for kids aged two to nine, the Pirates’ Cove Children’s Theme Park is a formidable way for the youngsters to burn off some energy while imaginatively exploring the park’s attractions.
They can climb aboard Pete’s 18-century Pirate Ship, go round and round on the Captain’s Carousel, watch an interactive show at the Swashbuckler Wharf Fun Stage, and plenty more.
Pirates’ Cove is only open in the warmer months of June through August.
58 – Go ice skating at Maggie Daley Park
Skating around in circles is boring; Chicago’s most exciting way to carve along the ice is undoubtedly the curvacious ribbon track at Maggie Daley Park (which, by the way, curls around a rock-climbing facility).
The outdoor course is positioned right under the sparkling Chicago skyline in the heart of Downtown – the perfect romantic selfie backdrop.
59 – Go on a jet ski safari on Lake Michigan
If you’re searching north of Downtown, head to Jet Ski Chicago by Lincoln Park.
If you’re hunting south of Downtown, they check out Chicago Water Sport Rentals at the 31st Street Harbor.
Either way, once you’re saddled into a roaring jet ski on the open waters of Lake Michigan, you’ll be grinning ear to ear.
60 – Catch a White Sox baseball game at Guaranteed Rate Field
As much as the locals love their deep-dish pizza, that love doesn’t quite compare to the obsession with the Chicago White Sox baseball team (although don’t say that to any Cubs fans).
Experience the famous White Sox atmosphere firsthand by catching an MBL match at Guaranteed Rate Field on the city’s South Side.
Sports fans can also swing by Wrigley Field, home to the Chicago Cubs. This beloved Major League Baseball stadium is a public institution in the city, and there’s no better way to spend a warm day than waiting for a home run in the stands.
Baseball buffs will certainly feel spoiled in the Windy City! The season typically runs from March to October, with concerts, pre-season matches, and events held at the stadium outside of those months.
61 – Marvel at the acrobatics of the Chicago Air & Water Show
Onlookers find themselves awe-stricken year after year at the annual (and free!) Chicago Air & Water Show – the most impressive of its kind across the country.
Grab a spot on the beach, tilt your head up to the sky, and hear the roar of the jet engines soaring overhead as military pilots perform astonishing stunts above the shimmering waters of Lake Michigan.
62 – Eat like royalty at the best Restaurants
From the classiest establishments to the most relaxed diners, there are culinary options for every palate in the Windy City.
Try the tasty cheeseburgers at Au Cheval, or the deluxe, multi-course menus at Alinea. Savor a hot dog at the retro SuperDawg Drive-In, or snag a slice of deep dish at Vito & Nick’s Pizzeria.
And if you like memorabilia with your meal, chow down under iconic instruments at the Hard Rock Cafe Chicago. Bring your loosest pants, because the city’s food scene is not to be missed!
63 – Feed a giraffe at Brookfield Zoo
Catch the kangaroos at Australia House, feed the giraffes at Habitat Africa, admire the alligators at The Swamp, and wander through plenty more exhibits at the renowned Brookfield Zoo.
With so many cute animal ambassadors ready for a meet-and-greet, Brookfield Zoo promises to be a great day out for the whole family.
Take the experience to the next level by competing in a zoo-wide scavenger hunt!
64 – Catch a game at Soldier Field
For almost 100 years, Soldier Field has been a beloved part of the city’s athletic scene.
For football fans, this is hallowed ground, as the home field of The Chicago Bears, who line up at Soldier Field during the season (typically September to February), foster a wild atmosphere – and the only way to really experience it is to join in on the action!
And if you prefer the other kind of football (soccer, that is), when visiting the Windy City, immerse yourself in that passion by attending a Chicago Fire match at Soldier Field.
Whether you prefer the NFL or the MLS, a day spent cheering in the stands is always a good time!
65 – Appreciate jazz at the Green Mill
Known across the city for its eclectic jazz performances and poetry readings, The Green Mill is a Chicago treasure.
It’s the oldest jazz club in the U.S., welcoming tourists since way back in 1907.
Celebrities and mobsters alike (from Charlie Chaplin to Al Capone) frequented this prohibition-era speakeasy over the years, and travelers continue to do so to this day.
66 – Catch a performance of the Chicago Symphony Orchestra
As the Chicago Symphony Orchestra edges its way toward 13 decades of captivating performances, it solidifies its reputation as one of the world’s best.
With brass, percussion, string, and woodwind instruments, coordinated by renowned Italian conductor, Riccardo Muti, it’s quite literally music to our ears.
Performances regularly take place at the Symphony Center in the Loop area.
67 – Listen to live blues at Buddy Guy’s Legends
Established (and still owned) by Grammy-winning Blues music maestro, Buddy Guy, this venue holds a special place in local hearts.
With live performances happening every day of the week, soaking in some of the best blues the city has to offer couldn’t be easier.
The menu serves up tasty New-Orleans-inspired dishes, the bar is stocked to the brim, and you can even grab a t-shirt souvenir on the way out!
68 – Stroll through Garfield Park Conservatory
Directly and easily accessible by the Green Line from Downtown, the 12-acre Garfield Park Conservatory (in the much larger Garfield Park) is a slice of nature’s paradise.
The free attraction is regarded as one of the most stunning botanic conservatories in the world, thanks to its thousands of plants and unique exhibits.
69 – See the light show at Buckingham Fountain
Once the sun starts to set, head over to the Clarence Buckingham Memorial Fountain in the center of Grant Park.
Before Cloud Gate (The Bean) came along, this historical landmark was Chicago’s most-visited attraction, thanks largely to its mesmerizing nightly light show.
The majestic attraction uses as much as 15,000 gallons of water per minute, and it all illuminates up after dusk.
70 – Interact with the exhibits at the Museum of Science and Industry
Showcasing an array of interactive and immersive activities, the Museum of Science and Industry is a fun, engaging, and informative day out for the whole family.
Headlining the incredible list of innovation and engineering-themed attractions are the mirror maze, 40-foot tornado simulator, and authentic German submarine.
It sits in the middle of Jackson Park, a perfect slice of nature to dive into a pre- or post-museum picnic.
71 – Laugh at the faces of Crown Fountain
While far less extravagant than the Buckingham fountain, the Crown Fountain takes the cake in the entertainment department.
It’s become famous for its Faces of Chicago element, where anonymous people are projected onto two identical 50-foot towers, appearing as though they’re spitting out a stream of water.
You’ll often spot kids running around in the fountain, trying to cool off on those sizzling summer afternoons.
72 – Explore the Richard H. Driehaus Museum
With a particular focus on the Gilded Age, the Richard H. Driehaus Museum takes visitors on a journey through the art, architecture, and design of the late 1800s.
It’s conveniently located just a couple blocks from Magnificent Mile, with a regular calendar of concerts and performances to complement the permanent exhibits.
73 – See a Broadway show at James M. Nederlander Theatre
Once a movie palace and vaudeville venue, the James M. Nederlander Theatre was recommissioned and restored to its original purpose: musical theatre!
Now, the decadent venue hosts a slew of Broadway shows, each more entertaining than the last.
Thanks to its central location near restaurants, bars, shops, and Millenium Park, it’s easy to spend a whole day without walking too far.
74 – Enjoy some Burlesque Shows
A vital and vibrant part of the city’s nightlife, the local burlesque clubs showcase an eclectic range of talent.
At Newport Peek, the evening’s performance might include belly dancing, drag shows, or avant-garde digital works.
Inventive and delightfully risque, these shows are not to be missed!
75 – Appreciate the vocals of the Lyric Opera of Chicago
Founded back in 1954, the Lyric Opera of Chicago has been acoustically dazzling its visitors for decades. The music is pitch-perfect, and the theatre’s foyer is as impressive as any in the city.
While attending any performance promises to be a remarkable showing in and of itself, keen visitors can upgrade their experience by booking a backstage, VIP tour.
Hungry? Dine at the Florian Opera Bistro before the show.
76 – Sample the best eateries at Time Out Market Chicago
The concept of the Time Out Market has recently swept the globe, with stations in Lisbon, New York, London, and, of course, Chicago – just to name a few.
Time Out Chicago boasts 18 unique eateries, spanning sushi to burgers and everything in between. Don’t miss Tony’s Rooftop Bar, the market’s crown jewel.
77 – Hop between Chicago’s rooftop bars
After soaking in the views from Tony’s Rooftop Bar at the Time Out Market, continue the rooftop adventures by hopping around some of Chicago’s very best patios and terraces.
Try the Elderflower Collins cocktail and take in the sweeping panoramic vista at Z Bar; sample a flight of local beers at the garden-themed Raised; or sit around a fire pit at Offshore, the largest rooftop bar in the world.
78 – Walk the Bloomingdale Trail (AKA The 606)
Chicago’s answer to Manhattan’s High Line, the Bloomingdale Trail (AKA the 606) takes visitors 2.7 miles across an elevated train track turned pedestrian walkway.
Multiple stairways are scattered from start to finish, allowing you to roam around the eclectic neighborhoods along the way.
Beer-lovers, make sure to take a half-hour to stop at the renowned Stenson Brewing Co.
79 – See the talent at the Laugh Factory
The Windy City is famed for its comedy scene, and you can sample it for yourself at the Laugh Factory. This lively venue has been a standup hotspot since 2011, featuring both headline acts and fresh talent.
If you’re feeling particularly adventurous, you can even try out one of their open mic sessions! Whether you’re watching old favorites or finding new ones, it’s the perfect place to forget your troubles and laugh until you cry.
80 – Head to the unique Dusty Groove vinyl store
Tucked away in the inner suburbs, the Dusty Groove vinyl store is the perfect example of Chicago’s extensive list of hidden gems that lay outside of the main tourist bubble.
The shop shelves thousands of records, eclipsing all genres, and the staff is delighted to chat about all things music.
81 – Grab some ice cream at Original Rainbow Cone
This longstanding Chicago ice creamery hibernates in the winter, but in the summer they’re teeming with elated customers and ice cream fanatics.
Visit the Original Rainbow Cone, choose from cones, milkshakes, sundaes, or banana splits, then burn off the calories with a pleasant stroll through the parks of Dan Ryan Woods.
How to get to Chicago?
The Windy CIty has two great airports to choose from: O’Hare and Midway.
Both offer a broad range of international and domestic flights, as well as easy access to the city itself. And with an airport transfer, you can simplify the process even further!
Where to stay in Chicago?
With its indoor pool, afternoon tea, and on-site spa, The Langham Chicago is so luxurious that you may want to stay in all day – but with the Magnificent Mile right outside the door, it’s well worth getting out!
In the same area, Sofitel Chicago Magnificent Mile offers everything from a spacious ballroom to a rooftop bar, all housed in a striking glass skyscraper.
Enjoy the elegant atmosphere of Club Quarters Hotel Wacker at Michigan, which offers contemporary amenities and a historic address; it’s housed in the Mather Tower, a gorgeous 1920s skyscraper known for its striking octagonal top levels.
And at the Congress Plaza Hotel, you can dine in, work out, and even get a haircut, before heading out to enjoy nearby attractions like the shores of Lake Michigan and the works at the Art Institute of Chicago.
Visiting Chicago on a budget?
If you want to see as many of the awesome sites as possible without going broke, there are some excellent options available.
The Go Chicago Explorer Pass allows you to pick between two and seven activities from a list of 25 beloved attractions.
The Chicago CityPASS focuses more on the top hits, providing discounted admission to the Field Museum, Shedd Aquarium, and Skydeck Chicago, as well as two additional complementary experiences from their roster.
Where to go next?
Chicago may be the big name in Midwestern tourism, but it has plenty of excellent neighbors to compete with! In Milwaukee, you can ignite your curiosity at museums, enjoy some professional sports action, or snap an action photo with The Fonz – The Bronze Fonz, that is!
Or head even further north to Minneapolis, home to a rich art scene, gorgeous public parks, and the iconic Mall of America. In St. Louis, you can stand at the banks of the mighty Mississippi, or scramble through the repurposed industrial world of the City Museum.
Indianapolis will quicken your pulse with its car races and professional sporting events, then lower it again with its scenic wildlife preserves and delicious restaurants. And if you head out to Detroit, you’ll find yourself awash in great theaters, jaw-dropping architecture, unique public art, and, of course, plenty of car-based attractions!
Final thoughts
For decades, the Windy City has been a beloved spot for visitors to revel in urban life. And with more amazing attractions each day – paired with a unique, nuanced history -, now is the perfect time to visit.
Whether you’re sporty or artsy, a food fanatic or an animal aficionado, you’ll find more than a lifetime’s worth of things to do in Chicago… so book your trip and get started!
Happy travels! 🙂