things to do in Chicago

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 world-famous museums. Dig into a slice of deep-dish pizza or dine at multi-Michelin starred restaurants. Whatever you choose to do, you won’t leave disappointed.

1 – Spend an afternoon at Navy Pier

Navy Pier, Chicago

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.

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 – See it all from the 360 Chicago Observation Deck

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.

3 – Catch a show at the Chicago Theatre

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.

4 – Soak in the skyline from a Lake Michigan sightseeing boat tour

Lake Michigan sightseeing boat tour

Get off your feet for a while; sit back and relax on a boat as the captain takes you down the Chicago River, 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.

5 – Race against the clock at an escape room

Chicago escape room

Race against the clock and put your teamwork and puzzle-solving skills to the test with an epic escape room challenge.

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.

Think you have what it takes to bust out? Sign up for one of the most fun things to do in Chicago and find out!

6 – Learn the true stories behind the city’s mob past

gangsters tour in Chicago

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!

7 – See the real Chicago on a street art tour

street art tour in Chicago

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!

8 – Feed a giraffe at Brookfield Zoo

Brookfield Zoo, Chicago

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!

9 – Take an architecture cruise on the Chicago River

Chicago River architecture cruise

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.

Tours typically last an hour and a half, and the guides are notably informative and entertaining.

10 – Explore the Lakefront on a segway tour

segway tour in Chicago

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.

11 – Experience Michelangelo’s masterpieces in an immersive photographic exhibition

Michelangelo's Photo exhibition Chicago

Can’t you travel to Rome and see the Sistine Chapel? No problem!

Go back in time visiting a full-scale photographic reproduction of Michelangelo’s masterpieces. The exhibition is created with a unique technique that makes the digital reproductions looking like paintings and frescoes.

The photographic exhibition reproduces 34 famous frescoes from the universe of Michelangelo.

12 – Eat and admire on the Spirit of Chicago dinner cruise

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.

13 – Embrace your inner Homer Simpson on an original donut walking tour

donuts tour in Chicago

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

bike tour in Chicago

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!

15 – Tour the Chicago River by kayak

kayak tour in Chicago

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.

16 – Get a bird’s eye view on a helicopter tour

helicopter tour in Chicago
credit to Tiqets

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.

17 – Feel the thrills of indoor skydiving

indoor skydiving in ChicagoIf 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.

18 – Admire the vast collections at the Field Museum Of Natural History

Field Museum of Natural History, ChicagoRegularly 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.

19 – Listen to jazz or classical concerts at candlelight

Candlelight Concerts Chicago

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.

20 – Get artsy at the Art Institute of Chicago

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.

21 – Get Even Artsier At The Museum Of Contemporary Art

Museum Of Contemporary Art, Chicago

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.

22 – Take A Selfie At Cloud Gate (AKA The Bean)

Cloud Gate, Chicago

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.

23 – Spot constellations at the Adler Planetarium

Adler Planetarium, Chicago

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.

24 – Kindle some romance on a sunset sailing tour

romantic sunset sailing tour in Chicago

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.

25 – Stand above Chicago at the Willis Tower Skydeck

Willis Tower Skydeck Chicago

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.

26 – Satisfy your palate on a food tour

food tour in Chicago

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.

27 – Wet your whistle on the Barrel Run

beer tasting tour in Chicago

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.

28 – Let your imagination run wild at the LEGOLAND Discovery Center

LEGOLAND Discovery Center, Chicago

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.

29 – Shop till you drop along The Magnificent Mile

The Magnificent Mile, Chicago

Comprising of over 460 retailers spread across three shopping centers, the Magnificent Mile lives up to its moniker.

Wander through clothing stores, souvenir shops, bookstores, and so much more; or take a locally-led walking tour to add a little extra flair to the afternoon.

30 – Step back in time on a prohibition tour

prohibition tour in Chicago

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).

31 – Devour a delicious brunch on the Chicago Odyssey Cruise

Chicago Odyssey brunch 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.

32 – Learn about architecture at Frank Lloyd Wright’s Home and Studio

Frank Lloyd Wright’s Home And Studio, Chicago

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.

33 – Let the kids run wild at the Chicago Children’s Museum

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.

34 – Tour the Frederick C. Robie House

Frederick C. Robie House, Chicago

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.

35 – Obsess Over Famous Wordsmiths At The American Writers Museum

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.

36 – Enjoy dinner and a show at Tommy Gun’s Garage

Tommy Gun’s Garage, Chicago

So long as you recall the entry password, a night of glamour, history, laughs, and intrigue awaits at Tommy Gun’s Garage.

As soon as you step through that front (armored) door, you’ll be transported back to the roaring 20s, a time when gangsters, flappers, and jazz ruled the streets.

While the dinner is delicious, the selling point is undoubtedly the entertainment. Song, dance, comedy, and even audience participation ring through the evening.

37 – Board the iconic tall ship Windy

Tall Ship Windy, Chicago

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.

38 – Make sightseeing competitive with a scavenger hunt

scavenger hunt in Chicago

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.

39 – Learn about the city’s past at the Chicago History Museum

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!

40 – Head to the Ernest Hemingway Birthplace Museum

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.

41 – Greet the animals at the Lincoln Park Zoo

Lincoln Park Zoo, Chicago

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.

It’s a fantastic excursion for the whole family – just remember to wear comfortable shoes.

42 – Dance the night away clubbing

clubbing in Chicago

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.

43 – Attend the Chicago Jazz Festival

Chicago Jazz Festival

Taking place annually over Labor Day Weekend in Millennium Park, Chicago’s Jazz Festival is a four-day, toe-tappin’ extravaganza.

Musicians venture from near and far to perform, free of charge, across multiple pavilions, for the thousands of visitors who regularly turn up.

It’s a scintillating atmosphere and an unmissable event, providing the dates coincide with your visit.

44 – Rent a private luxury boat (with pizza included!)

private boat in Chicago

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.

45 – Visit the DuSable Museum of African American History

DuSable Museum of African American History, Chicago

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.

46 – Walk with butterflies at the Peggy Notebaert Nature Museum

Peggy Notebaert Nature Museum, Chicago

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!

47 – Learn about Latin culture at the National Museum Of Mexican Art

National Museum Of Mexican Art, Chicago

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.

48 – Unleash the youngsters at Pirates’ Cove Children’s Theme Park

Pirates' Cove Children's Theme Park, Chicago

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.

49 – Go ice skating at Maggie Daley Park

ice skating at Maggie Daley Park, Chicago

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.

50 – Go on a jet ski safari on Lake Michigan

jetski on Lake Michigan, Chicago

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.

51 – Catch a White Sox baseball game at Guaranteed Rate Field

White Sox baseball game at Guaranteed Rate Field, Chicago

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.

Alternatively, head to Wrigley Stadium to catch the Cubs in action, an absolute must when it comes to things to do in Chicago.

The season typically runs from March to October, with concerts, pre-season matches, and events held at the stadium outside of those months.

52 – Marvel at the acrobatics of the Chicago Air & Water Show

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.

53 – Cheer on the Chicago Blackhawks hockey team at the United Center

Chicago Blackhawks hockey at the United Center

For the hockey fanatics, it would be a sin to leave Chicago without fronting up to a Blackhawks game.

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.

54 – Watch the Chicago Bulls play at the United Center

basketball game, United Center in Chicago

With the legacy of Michael Jordan etched into NBA and sporting folklore, the Chicago locals absolutely adore their Bulls.

The team’s regular home games are played at the United Center and run from October to April – presenting a fantastic opportunity to escape the wind and the cold.

In terms of getting there, the Blue Line which stretches through Downtown drops you off within walking distance.

55 – Barrack for the Bears at a Soldier Field NFL game

Soldier Field NFL game, Chicago

If hockey, basketball, baseball, or soccer don’t spark much of an interest, there’s one more sport on offer which the locals take religiously: football.

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!

56 – Feel the vibe at the Millennium Park Summer Music Series

Millennium Park Summer Music Series, Chicago

Every year – come rain, hail or shine – the city of Chicago puts on an exciting lineup of outdoor concerts at the Pritzker Pavilion in Millennium Park from June through August.

Past performers have spannel the entire genre spectrum, from jazz and orchestral music to dance vibes, indie rock, and country. Best of all, it’s totally free.

57 – Scream your lungs out at Lollapalooza Music Festival

Lollapalooza music festival, Chicago
Chicago native rapper Saba performs at Lollapalooza in Grant Park, Chicago.

Lollapalooza is one of the largest and most famous music festivals on the planet, and it surfaces every year in the middle of none other than the Windy City.

The wild event spans four days in late July or early August, with hundreds of local and international artists pumping out their best tunes for the tens of thousands of screaming fans.

Past headliners have included The Strokes, The Chainsmokers, Ariana Grande, And Twenty One Pilots – it’s a big deal and tickets sell out quickly.

Festival-wise, it’s not only one of the best things to do in Chicago but one of the best things to do across the entire country!

58 – Appreciate jazz at the Green Mill

The Green Mill jazz club, Chicago

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.

59 – Listen to live blues at Buddy Guy’s Legends

Buddy Guy’s Legends, Chicago

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!

60 – Catch a performance of the Chicago Symphony Orchestra

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.

61 – Stroll through Garfield Park Conservatory

Garfield Park Conservatory, Chicago

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.

62 – See the light show at Buckingham Fountain

Buckingham Fountain light show, Chicago

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.

63 – Interact with the exhibits at the Museum of Science and Industry

Museum Of Science And Industry, Chicago

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.

64 – Laugh at the faces of Crown Fountain

Crown Fountain, Chicago

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.

65 – Explore the Richard H. Driehaus Museum

The Richard H. Driehaus Museum, Chicago
credit to 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.

66 – See a Broadway show at James M. Nederlander Theatre

James M. Nederlander Theatre, Chicago
credit to 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.

67 – Appreciate the vocals of the Lyric Opera of Chicago

Lyric Opera of Chicago
credit to 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.

68 – Feed yourself at the Taste of Chicago Festival

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.

69 – Skip the lines at Au Cheval Restaurant

Au Cheval restaurant, Chicago
credit to Au Cheval restaurant

People wait in line for hours to try Au Cheval‘s famous no-frills cheeseburger, which should tell you just about everything you need to know about this restaurant’s popularity and quality.

Despite only opening a few years ago, Brendan Sodikoff’s diner has quickly found its way into the spotlight.

To avoid the lines, visit during the week, outside of peak lunch and dinner lines.

70 – Experience unrivaled luxe dining at Alinea

Alinea fine dining restaurant, Chicago

Alinea calls themselves “not a restaurant” – instead, they refer to themselves as a culinary experience. It might seem odd, but with three Michelin stars under their belt, they can do as they please.

The ultra-modern haunt offers three high-class, unique experiences: 1) The Gallery Menu, a multi-sensory 16-to-18 course menu, 2) The Kitchen Table, a completely private dining experience in the company of the chefs, 3) The Salon Menu, a more affordable 10-12 course tasting menu.

71 – Sample the best eateries at Time Out Market Chicago

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.

72 – Hop between Chicago’s rooftop bars

rooftop bars in Chicago

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.

73 – Eat in your car at the Superdawg Drive-In

Superdawg drive-in, Chicago

So long as you don’t mind a few crumbs in the car, the Superdawg Drive-In is an absolute staple for tourists and visitors alike.

The joint is best known for their hot dogs (or Superdawgs, as they’re known), but they also serve sandwiches, burgers, desserts, and ice cream.

74 – Order a slice at Vito & Nick’s Pizzeria

Vito & Nick's Pizzeria, Chicago

Contrary to Chicago’s deep-dish pizza reputation, Vito & Nick’s Pizzeria has been dishing up ‘Cracker Thin Crust Pizza’ since the 1950s, and they’ve yet put a foot wrong.

A visit to this adored eaterie and you’ll feel like you’ve stepped back in time into an old-world Chicago dive restaurant.

This isn’t luxury nor sophistication, it’s just darn good pizza.

75 – Walk the Bloomingdale Trail (AKA The 606)

Bloomingdale Trail, Chicago

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.

76 – Head to the unique Dusty Groove vinyl store

Dusty Groove vinyl store, Chicago

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.

77 – Grab some ice cream at Original Rainbow Cone

Original Rainbow Cone, Chicago
credit to 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.

78 – Get a massage at the Chicago spas

spa in Chicago

After walking around the Windy City, there’s no better way to relax and unwind than with a couple of hours being pampered at one of Chicago’s many well-respected beauty and wellness spas.

For a chance to connect with your partner on a deeper level, consider the couples’ massage option — any tension will be gone, and you’ll feel like you’re walking on a cloud!

79 – Dig in at the Hard Rock Cafe Chicago

Hard Rock Cafe, Chicago

The burgers are towering, the energy is high, and the atmosphere is rocking at Chicago’s very own Hard Rock Cafe.

Dine in for lunch in between activities, or grab some dinner before heading out barhopping in River North – either way, you won’t be disappointed with the multi-course thoroughfare.

80 – Watch the Chicago Fire soccer team at Soldier Field

Chicago Fire soccer team at Soldier Field, Chicago

Soccer might not be the most popular sport in the US, but its fans are as loud and as passionate as any.

When visiting the Windy City, immerse yourself in that passion by attending a Chicago Fire match at Soldier Field.

If you’re looking for a few hours to kill before kickoff, head to the Field Museum right next door.

Looking for more things to do in Chicago? Check out TourScanner’s full list of tours and activities in Chicago. If you know other cool places to visit in Chicago, do not hesitate to comment below.