101 Things to Do in Chicago

Chicago may be known for its deep dish pizza and soaring skyscrapers but locals know there are more things to do in Chicago than just eat pizza. There truly is something for everyone in what we locals affectionately call the Windy City, whether you love bold architecture, a range of culinary delights, world-class museums or the call of the beaches along Lake Michigan.

Chicago is a city of neighborhoods and each one truly has its own personality. Since the city was built on a grid after the Chicago Fire of 1871, it’s relatively easy to get around using a number of transportation options, whether it’s by foot, car, Chicago Public Transit (CTA) buses or trains, or Divvy, our popular and affordable bike share program.

The best things to do in Chicago

No matter where you land in this city, some of the best things to do in Chicago are free, but there’s also so much to do that you can stay busy 365 days of the year. Here’s a cheat sheet to get you started with 101 of the best things to do in Chicago. Check current hours and availability before heading out.

1. Take a selfie in front of The Bean

The Bean, Chicago, IL

Source: Adam Alexander Photography Photo Courtesy of Choose Chicago

One of the city’s most popular public sculptures and a magnet for selfies thanks to its mirror-like exterior is Cloud Gate, also known as The Bean, by Anish Kapoor.

2. Take a free, self-guided tour of Graceland Cemetery

Many of Chicago’s most powerful citizens and leaders, as well as famous architects, have been laid to rest in this beautiful cemetery that’s also a registered arboretum. Download a free map online or pick up a copy at the cemetery office.

3. Channel peace and calm at the peace circle at South Shore Nature Sanctuary

Adjacent to the South Shore Beach and located within the South Shore Cultural Center Park sits a nature sanctuary, which includes six acres of dunes, wetlands, woodlands and prairies. Take a walk along the short boardwalk and enjoy some stunning views of Lake Michigan and the city’s skyline.

4. View the city from the Willis Tower Glass Ledge

Chicago has so many skyscrapers in the Loop and beyond that it’s possible to get outstanding skyline views in many of its tall buildings. But the Skydeck, located 103 floors above the ground in the Willis Tower (formerly Sears Tower), is still pretty neat to experience. Take in views extending to four states in one its clear observation boxes.

5. Find Instagram-worthy murals in the South Loop

Wabash Arts Corridor, Chicago, IL

Photo courtesy of Megy Karydes

While the program officially ended in 2017, the Wabash Arts Corridor in the South Loop continues to draw locals and visitors alike to enjoy murals that use buildings as their canvas.

6. Tour Chicago’s murals and mosaics

Public art is visible throughout the city but its murals and mosaics throughout a pretty special. In addition to the Wabash Arts Corridor, there are dozens of murals to be found and enjoyed.

7. Bowl at UIC

For no-frills and cheap bowling, head to the basement of UIC’s Main Building. Since this bowling alley is pretty obscure, it’s rarely crowded, making it a fun afternoon or evening to hang out with friends.

8. Walk the Art Walks

From Wicker Park to Pilsen and Bronzeville, River North isn’t the only neighborhood that hosts regular art walks. For an up-to-date list of all the art walks throughout the city, check out Chicago Gallery News.

9. Do a kick flip at Grant Park Skate Park

Chicago may have a flat topography but there are several skate parks throughout Chicago that welcome skaters, including Grant Park.

10. Channel your inner artist at the Art Institute of Chicago

Whether you’re just starting out or want to build your portfolio, the Art Institute of Chicago offers a host of classes for adults.

11. Bind a book at Bari Zaki Studio

Bari Zaki, Chicago, IL

Photo courtesy of Megy Karydes

Fans of all things of paper and writing utensils will fall in love with Bari Zaki’s Lincoln Square studio featuring such accouterments. Take your obsession to the next level and try your hand at one of her bookbinding classes.

12. Make your own sneakers at the Chicago School of Shoemaking and Leather Arts

Have just a couple of hours? Make a leather belt! Or, step it up and make your own kicks, whether its sneakers, sandals or boots, over the course of one to three days.

13. Find the potholes

Normally, one tries to avoid potholes at any cost, unless you stumble upon one by Jim Bachor. The Chicago-based artist uses mosaic to fill in potholes. A map showing where to find the unusual art installations can be found on his website.

14. Feast like a king on a pauper’s salary at Kendall College

Enjoy a fine dining experience but at a fraction of the cost at The Dining Room, where culinary students use fresh and seasonal ingredients from its own herb and vegetable garden, as well as Green City Market to create their menu.

15. Hike the Big Marsh

Again, given Chicago’s flat topography, “hiking” anywhere might be a bit of a stretch but that doesn’t stop us from finding places to walk. Head to the southeast side of the city to hike or off-road bike the Big Marsh. The 280-acre property is also known as the Calumet Area Reserve, and about 45 acres have been developed for a number of outdoor activities, including hiking, adventure courses and off-road biking.

16. Cheer on the Cubs at Wrigley Field and the White Sox at Guaranteed Rate Field

Wrigley Field on the city’s north side is the second-oldest ballpark (Boston’s Fenway Park is the oldest) and the Chicago Cubs enjoy some of the most loyal fans, having won three World Series. The White Sox team also has won three World Series titles and plays on the south side. Cheer on your favorite team when they play each other during the season.

17. Take a selfie with Harry Caray

A bronze statue of Harry Caray is located near the Wrigley Field’s bleachers, commemorating the legendary Chicago Cubs announcer.

18. Gather at Kusaya Café

Enjoy some coffee, breakfast and lunch with a side of community and arts events at this non-profit coffee shop in Englewood.

19. Fill your potions chest at Merz Apothecary

This isn’t your average neighborhood pharmacy. This family-owned and -run pharmacy has been part of Chicago since 1875 and offers dozens of unique, some hard-to-find and natural products from all over the world.

20. Skate the ribbon at Maggie Daley Park

During the winter, bring your own skates and skate the ice skating ribbon at Maggie Daley Park. In the summer, it transforms into an outdoor roller skating rink. The 20-acre park also features a fun park for kids and will soon offer mini-golf, too.

21. Walk this West Town alley and enjoy an art gallery

West Town Art Gallery, Chicago, IL

Photo courtesy of Megy Karydes

In a nondescript alley between Noble and Bishop streets, homes or apartments for those who live on Ohio and Erie streets in West Town is an art gallery of a different sort. Artists and muralists from Chicago and around the world have transformed garages and buildings into works of art.

22. Feel the magic at Walt Disney’s birthplace

It may not be Disney World but Walt Disney was born in Chicago’s Hermosa neighborhood before moving with his family when he was four years old. After years of private residential ownership, the Walt Disney birthplace home has been bought by a non-profit organization that’s raising money to restore it to its original state and earn Landmark status to preserve it. While no tours are available, you can still stop by and pay homage to the man who brought magic to life.

23. Avoid pedestrian traffic by using the underground pedway

Most people don’t know there’s an underground pedway that connects more than 50 downtown buildings. It’s especially convenient during inclement weather but also anytime you want to avoid dealing with the crowds above.

24. Laugh it up at Logan Square Improv

Find up-and-coming improv talent at Logan Square Improv for just $5 a show. It’s BYOB, and the tiny venue fills up fast so best to arrive early.

25. Admire the stained glass windows in the pedway

Who would have thought to add 22 American Victorian stained glass window displays underground? Permanently displayed backlit glass artwork greet those who walk the pedway below Randolph Street between Wabash Avenue and State Street.

26. Stand in line and wait for your Italian ice

Mario

Photo courtesy of Megy Karydes

A staple since 1954, Mario’s Italian Lemonade in Little Italy is a popular warm-weather draw for locals. Don’t be surprised if you spot a celebrity or member of one of Chicago’s athletic teams waiting alongside you for their Italian ice, too.

27. Experience live jazz at the Museum of Contemporary Art

Tuesday on the Terrace features live jazz musicians weekly at 5:30 p.m. for free.

28. Eat Chicago deep dish pizza where it all began

Pizzeria Uno is said to be where Chicago deep dish pizza is to have originated when Ike Sewell concocted what is now ubiquitous with Chicago-style dining. Fans still line up at its River North location for their slice of heaven.

29. Listen to Chicago Blues legends

Chicago has its own sound — literally and figuratively. In our case, it’s the Chicago Blues. Enjoy this soulful cadence at any one of its many Chicago Blues clubs where living legends including Lurrie Bell or Billy Branch and the Sons of Blues play regularly.

30. Catch Paper Machete dish it out at Green Mill

A weekly “live magazine” format performance, The Paper Machete delights guests every Saturday afternoon at the Green Mill Cocktail Lounge in Uptown. When the puppet isn’t entertaining (you’ll have to attend a show to understand the reference), the jazz nightclub is popular among locals and visitors alike. Take a minute to enjoy the memorabilia along the wall as you enter of Al Capone’s time hanging out at the club.

31. Laugh it up with Funny Ha-Ha at The Hideout

Chicago’s bars and clubs often do double-duty to cater to an eclectic clientele and The Hideout is no exception. When the Prohibition-era bar isn’t serving up cheap drinks or hosting dance parties, it’s hosting one of Chicago’s favorite literary humor reading series: Funny Ha-Ha.

32. Visit the Historic District of Prairie Avenue and take in a haunted reading

Prairie Avenue Houses, Chicago, IL

Credit: City of Chicago Photo Courtesy of Choose Chicago

Once home to some of Chicago’s founding families, including those of Marshall Field, George Pullman and Philip Armour, the Historic District of Prairie District Avenue in the Near South Side was built after the Great Fire of 1871 by notable architects such as Daniel Burnham and Henry Hobson Richardson.

Once called Millionaires’ Row, some homes still stand today, including the Glessner House (designed by Richardson) which has been converted into a museum and hosts the very-popular Edgar Allan Poe Readings by Lifeline Theatre annually around Halloween. Tickets sell out very quickly (trust me, I’ve been trying to score some for years) so best to act fast if you want to attend the staged readings.

33. Discover the History of the Pullman District

Speaking of historic districts, even many Chicagoans don’t know the history behind the Historic Pullman District. It was built from 1880 to 1884 when George Pullman decided to build the community in Chicago for the employees of his Pullman Palace Car Company.

One weekend a year, residents of Pullman open up their homes for the annual Historic Pullman House Tour where visitors can check out 120-year-old landmark homes that include executive mansions to 14-foot wide workers’ cottages to multi-unit apartments. Outside that one weekend, the National A. Philip Randolph Pullman Porter Museum details the work of Pullman’s porters and their contributions to the labor movement.

34. Get Smart on Art at the Smart Museum of Art

Most locals know of the Art Institute of Chicago and the Museum of Contemporary Art but rarely do they bother to visit the many other art museums throughout the city, including the Smart Museum of Art on the University of Chicago’s Hyde Park campus. In addition to rotating exhibits and a permanent collection, the museum offers year-round public programming — all free thanks to its SmartPartners.

35. Take your High Tea at The Drake

For a century, guests have enjoyed afternoon tea at Palm Court within The Drake hotel, which has received royal visits from Queen Elizabeth II and Princess Diana, as well as celebrities such as Marilyn Monroe. To step it up a notch, opt to reserve your tea time to coincide with the guided History Tour and Tea.

36. Head to the home goods store to dine under a crystal chandelier and stars

Admittedly, going through living room collections at Restoration Hardware before heading off to an elegant brunch or dinner might seem odd but that’s exactly what you can do when you make reservations at the 3 Arts Club Café in the shop’s flagship located within a more than century-old Gold Coast building. Find any celebration or make one up if you need an excuse to visit.

37. Learn 70 new languages or read thousands of books for free

One of the best services available to all Chicago residents is its massive Chicago Public Library system. In addition to thousands of books available, you can download audiobooks, read magazines and newspapers, as well as sign up to learn up to 70 languages — all available for free.

38. Check out the busts in the Loop

Chicago Water Taxi, Chicago, IL

Photo courtesy of Megy Karydes

Take a walk along the north side of the Chicago River in the Loop to find the eight American retail merchants giants, including Montgomery Ward and Frank Winfield Woolworth at the Merchandise Mart, then head east to find Jack Brickhouse, Hall of Fame Broadcaster, whose bronze statue holds court on Michigan Avenue.

39. Visit the house that Jordan built and take a selfie with The Spirit

Michael Jordan is arguably one of the best NBA players ever and his contributions to the Chicago Bulls are forever memorialized through a bronze statue of his likeness in a spread eagle dunk, also known as The Spirit, located at the United Center on the city’s Near West Side. Don’t miss the opportunity to take a selfie in front of the 16 1/2 foot tall sculpture.

40. Window shop the Mag Mile

Lined along Michigan Avenue just north of the Chicago River are retail flagship stores of brands you see in major magazine spreads: Burberry, Gucci, Louis Vuitton, Nike and Salvatore Ferragamo among them.

41. Tour Starbuck’s largest coffee roastery

After your retail therapy along the Mag Mile ends, hop over to Starbucks Reserve Roastery at 646 N. Michigan Ave., the five-floor and 35,000-square-foot (no, that’s not a typo) coffee bar, roastery, bakery, café, cocktail bar and more that also claims the title of the company’s largest roastery.

42. Cook up a feast at The Chopping Block

With two locations, one in the Merchandise Mart and one in Lincoln Square, and dozens of classes a month at each location, it’s easy to find one that fits your schedule and interest. From pasta boot camps to macaron workshops, there truly is something for everyone.

43. Get whimsical with Whimsical Candy

Hidden on a lower level of a Chicago Loop business building, Whimsical Candy delights fans with its handmade signature chews of white chocolate nougat and sea salt caramel dipped in dark chocolate, caramels, nougat bars and fruit candy, among other pastry delights. The cheerful shop may be tucked away but its customers know they’re in for a treat once they head down that hallway.

44. Learn about great American scribes at the American Writers Museum

Also seemingly tucked away in a downtown office building but this time on the second floor is the American Writers Museum. An interactive museum that engages the senses and encourages touch, in addition to honoring great American writers, including writers of color and women, it hosts rotating exhibits, author readings and children’s storytime.

45. Admire the largest Tiffany stained-glass dome at the Chicago Cultural Center

Chicago Cultural Center, Chicago, IL

Credit: City of Chicago Photo Courtesy of Choose Chicago

Considered the largest Tiffany dome in existence, it’s also free to view at the Chicago Cultural Center in the Loop. The 38-foot-diameter dome includes 1,134 square feet of mosaics and 30,000 individual panes of glass.

46. Check out the largest Tiffany mosaic in existence at Macy’s

As if the largest Tiffany dome weren’t enough, Chicago has another stunning Tiffany piece within Macy’s on State Street in the Loop. View the stunning 6,000-square-foot Tiffany ceiling of 1.6 million pieces of iridescent glass from the first-floor cosmetics department and head to the fifth floor for a closeup.

47. Make reservations early to dine at The Walnut Room during the holidays

It’s become a tradition among many families and friends to dine at The Walnut Room when the 45-foot-tall Great Tree goes up in late November until early January. The tree is lit up with 15,000 lights and makes for a special holiday ambiance. The historic restaurant is open year-round as well to enjoy.

48. Pass the jewels and hit up some of the best Middle Eastern fare in the Loop

You’ll have to pass several fine jewelry displays before you make it to Oasis Café but once you do, you’ll be rewarded with some of the tastiest Middle Eastern fare available to those who work, study and play in the Loop. Located at 21 N. Wabash Ave. in the heart of Jewelers Row, it’s popular among professionals during their lunch break so expect a line if you don’t plan ahead.

49. Get your fix of medical oddities at Woolly Mammoth Antiques and Oddities

If you’re in the market for anatomy items like, oh, you know, skulls, bones or skeletons, then head over to Woolly Mammoth Antiques and Oddities in Andersonville where the quirky shop stocks all these and more.

50. Take your love of medicine a step further at the International Museum of Surgical Science

Four floors and 10,000 square feet of public galleries await guests at this unique museum, North America’s only one devoted to surgery, which includes a permanent collection of art and artifacts from the history of Medicine.

51. Outfit your home with Chicago architectural artifacts

If you’re looking for a pair of windows designed by architect George Maher or Frank Lloyd Wright, decorative balusters from the Robert Roloson Houses, your best bet is to check out Architectural Artifacts. If archaeologist, collector and owner Stuart Grannen doesn’t have it, it’s unlikely it’s available for sale.

52. Hit up a new farmers market

Most Chicagoans have a nearby farmers market that sells fresh and seasonal produce but why not mix it up on some weekends and try a new one across town? Or, hit up the one at Daley Plaza, Chicago’s longest-running farmers market, or swap recipes with some of the city’s finest chefs as they shop for their restaurants at Green City Market.

53. Visit one of the oldest zoos in America

The Lincoln Park Zoo has been delighting guests since 1868 when it was founded and is also one of the few zoos that offers free admission. Thousands of animals and other living and diverse species call this 35-acre campus home.

54. Admire the ancient ferns at the Lincoln Park Conservatory

Lincoln Park Conservancy, Chicago, IL

Photo courtesy of Megy Karydes

With the skyline as its background and the Zoo its neighbor, the Lincoln Park Conservancy includes lush and exotic plants from around the world within a stunning Victorian glass house built between 1890 and 1895. Admission is free to wander its four display houses of ancient ferns, palms, orchids and more.

55. Meander through the Alfred Caldwell Lily Pool

It seems impossible to find such a serene oasis just a few steps away from busy Fullerton Parkway and Lake Shore Drive but within Lincoln Park is this darling and quiet lily pool designed by landscape architect Alfred Caldwell. Last time I visited, a beautiful crane was hanging out in one of the park’s native trees. Don’t miss the council ring once you continue along the stone walk throughout the space.

56. Get lost in nature at Promontory Point

Continuing our love affair with all things outdoors and nature, Alfred Caldwell is also responsible for the design at Promontory Point on the city’s south side, specifically within Burnham Park. Some say the site is one of the best places to take a view of Chicago’s skyline.

57. Bike, ride, walk, run and enjoy the Lakefront Trail

The scenic Lakefront Trail offers 18 miles of paved trail that follows Lake Michigan’s shoreline from the north side to the south and is popular among locals and visitors alike.

58. Tour Frank Lloyd Wright’s Robie House

Most of famed architect Frank Lloyd Wright’s designed homes are in the neighboring suburb of Oak Park but the Frederick C. Robie House, considered his best-known Prairie masterpiece, is a U.S. National Historic Landmark and sits on the University of Chicago’s Hyde Park campus. Tours are available year-round.

59. Circle the Circular Economy at The Plant

Located in the Back of the Yards neighborhood on the city’s south side are dozens of ambitious and visionary business leaders who are helping create a circular economy. Individuals can support their work by attending one of their many workshops or shopping their farmers market on Saturdays.

60. Touch a piece of the world on Michigan Avenue

While the Tribune Tower is no longer home to those who work for the Chicago Tribune, the building’s façade includes historic fragments, all labeled, from around the world collected by its correspondents. The 149 or so pieces include bits of the Notre Dame Cathedral in Paris, the Berlin Wall and twisted metal from the World Trade Center after 9/11.

61. Escape Chicago’s winters at the Garfield Park Conservatory

Garfield Park Conservancy, Chicago, IL

Photo courtesy of Megy Karydes

The west side conservatory is an oasis from the city any time of the year but it’s one of the best things to do in Chicago during the cold months when we’re craving some warmth and greenery (hello, Desert House!). There are many delightful rooms to visit among the 184-acre park and no matter the season, there’s always something new to see, smell, touch and enjoy. Oh, and it’s free to visit.

62. Find your Zen 94 Stories high with Sky Yoga

Experience 360 Sky Yoga at 360 Chicago, a weekly sky-high yoga series. Find your Zen more than 1,000 feet above Chicago in these hour-long sessions.

63. Enjoy a cocktail with a view at Cindy’s

Chicagoans love their rooftop bars and Cindy’s Rooftop is among the most coveted thanks to its rockstar view: The Bean, Millennium Park and Lake Michigan. It doesn’t hurt that it’s located within an 1893 building with its own architecturally-rich history — the Chicago Athletic Association.

64. Restrict the urge to slide down the Picasso

The 50-foot-tall untitled sculpture by Picasso is one on the city’s iconic public pieces of art and while it’s not intended to be a playground, you’d be hard-pressed to pass it on any given day and not see kids (or adults) climbing it and trying to slide down the piece.

65. Relax in the Drawing Room at the Chicago Athletic Association

Not restricted to its hotel guests, the Drawing Room on the second floor of the Chicago Athletic Association is a wood-paneled living room of sorts with darling seating areas throughout and tall windows overlooking Millennium Park. Change up your relaxation or work routine and head here instead. Order a drink or something to eat off the menu, and either bring a book to read or plug in your laptop at one of the hottest hangout spots in the city.

66. Meander The 606

The 606 Bloomingdale Trail may not be Chicago’s longest by a long shot (it’s only 2.7 miles) but its location is what makes this trail particularly important. Most trails in the city run north and south, which makes getting from east to west a bit longer. But this much-awaited elevated trail on the northwest side helps alleviate some traffic below and makes it safer to bike, ride or walk these parts.

67. Cruise the river

There are more than half a dozen companies that offer Chicago River cruises, most of which are focused on the architecture of the city. Even locals who are familiar with the city’s history find an afternoon or evening river cruise a delightful and different way to see Chicago.

68. Or kayak the river

Use your own body’s energy to see the city through the lens of the Chicago River by kayaking it. Bring your own kayak to a boathouse or other safe location (check out Openlands for a list of spots) or rent one from companies like REI or Urban Kayaks for another unique way to enjoy the river.

69. Or take a stroll down the Riverwalk

If being in the river doesn’t excite you or you just want to soak in the waterway, perhaps a stroll along the newly-designed and completed Chicago Riverwalk might be an option. The 1.25-mile long continuous path includes gardens, as well as restaurants and cocktail bars.

70. Stop and smell the roses and more at Lurie Garden

RJ - Lurie Garden, Chicago, IL

Photo Courtesy of Choose Chicago / Lurie Garden

No matter the season, Lurie Garden in Millennium Park is a welcome sight and form of inspiration to many. From winter’s slumber where snow might cover much of the garden to summer’s lush landscape, Lurie Garden is truly a living museum. It’s a 2.5-acre garden filled with perennials, bulbs, grasses, shrubs and trees.

71. Appreciate the not-so-subtle reminder to do your duty when your dog does its duty

It seems like no city is exempt from dog walkers who fail to pick up after their pets do their thing and while signs are good reminders for some, one artist took it a step further and created a permanent bronze sculpture called Shit Fountain. Pay your respects by visiting the sculpture located on the artist’s property just east of Ukranian Village at 1001 N. Wolcott Ave.

72. Ride the Centennial Wheel at Navy Pier

Head almost 200 feet into the air on the Centennial Wheel (also known at the Ferris Wheel at Navy Pier). Enjoy 360-degree views year-round since you’ll be soaring into the sky in an enclosed gondola.

73. Visit a museum named after America’s first woman to win a Nobel Peace Prize

In 1931, Jane Addams became the country’s first woman to win the Nobel Peace Prize and the settlement house that she co-founded in 1889 today bears her name as part of her legacy. The Jane Adams Hull-House Museum honors the work she did to help immigrants and shape national and international policy by sharing more than 5,000 artifacts related to her work and that of the surrounding neighborhood. Free public tours are available.

74. Fish Northerly Island

What was once a single runway airport until then-Mayor Richard M. Daley ordered its demolition literally overnight has since become a 119-acre urban sanctuary. To access the island’s wonder and beauty, head to the Adler Planetarium as it’s just behind it. Among Northerly Island’s offerings are a five-acre pond, strolling paths, more than 150 different varieties of native plants and an emerging savanna with 20,000 trees and shrubs. Camping, fishing and paddling are permitted, as well.

75. Check out Chinatown

Many cities have wonderful Chinatown communities but Chicago’s Chinatown is vibrant, colorful and full of purveyors offering delicious Chinese and Asian cuisine, baked goods and teahouses. The main crossroads are Cermak Road and Wentworth Avenue. Check out the Nine-Dragon Wall, a reproduction of the 15th-century mural of the one in Beijing along your stroll and then stop in any of the restaurants for a meal. Afterward, enjoy some refreshing boba teas at Tsaocaa.

76. Play it up at Pritzker Pavilion

From late spring to early fall, the Pritzker Pavilion becomes an adult playground. Visitors often pack a picnic and find a spot on the lawn to enjoy free movies, performances and live concerts.

77. Get lost finding the trees

When Chicago was faced with dealing with trees that were infected with the emerald ash borer, it turned to artists. The Chicago Tree Project artists transformed these trees into works of art. An audio tour is available, as well as a map to locate each tree sculpture.

78. Brush up on Chicago history

History Museum, Chicago, IL

Credit: Clayton Hauck Photo Courtesy of Choose Chicago

Located at the southern edge of Lincoln Park, the Chicago History Museum includes several permanent and rotating exhibits. Among the most popular involves being able to become one with a Chicago-style hot dog (part of the Sensing Chicago exhibit!).

79. Admire the renowned artists at the Art Institute of Chicago

Pass the pair of bronze lions and enjoy some 300,000 works of art, from paintings such as Georges Seurat’s “A Sunday on La Grande Jatte” to more modern pieces like the sculpture by Katharina Fritsch called “Woman with Dog (Frau mit Hund)”.

80. Explore modern art at the Museum of Contemporary Art

Visitors to MCA can enjoy modern works from the likes of Virgil Abloh to Frida Kahlo. On select Sundays, kids (and adults) can make reservations at its on-site restaurant, Marisol, for Drag Queen Story Time and brunch.

81. Enjoy some history with your ice cream at Margie’s

Expect to wait to score a seat in the tiny Margie’s Candies on Western Avenue but it’ll be worth the wait to enjoy one of their delightful ice cream sundaes or other concoctions. Celebrities, sports stars and even The Beatles have stopped by for their sugar fix.

82. Catch some of the best smoked fish at Calumet Fisheries

Chicago may be known for a lot of things but great seafood isn’t among them since we’re not, well, near any ocean. But Calumet Fisheries has a cult-like following for good reason. It offers some of the best house-smoked fish, fries and seafood platters from a no-nonsense seafood shack on the city’s far south side.

83. Frolic around Crown Fountain

When the two 50-foot glass block towers were first built, traffic nearly came to a standstill as Chicago watched the photos of residents projected. The images were arranged in such a way that it gives the illusion that water is sprouting from their mouths. The interactive work of public art by Catalan artist Jaume Plensa has become a fun summer tradition for thousands of kids (and adults) to cool off and frolic in the water.

84. Take in the water display at Buckingham Fountain

Buckingham Fountain, Chicago, IL

Credit City of Chicago Photo Courtesy of Choose Chicago

From mid-May to mid-October, Buckingham Fountain, one of the largest fountains in the world and located in Grant Park, puts on a major water display every hour for 20 minutes.

85. Be inspired to create art with someone’s trash from The WasteShed

What does one do with extra art supplies or those one no longer needs? Donations of gently-used art supplies are sold at deep discounts at The WasteShed in Humboldt Park for both budding and seasoned artists and makers.

86. Head to Lem’s for Ribs

There’s no place to sit. There’s barely any parking available. The place only takes cash. Yet Lem’s Bar-B-Q on the south side is so well-known for its rib tips and hot links that people will form a line and wait outside through the elements, if necessary, because it’s that good. Some of us may or may not have taken our bag of goods next door to Frances Cocktail Lounge to enjoy our hot meal with a cold beer.

87. After Lem’s, stop at Brown Sugar Bakery for a sweet treat

James Beard Award-nominee Brown Sugar Bakery is known for its decadent cakes, which you can also enjoy by the slice.

88. Relax and read at the Harold Washington Library

You can’t miss the HWL with its five large owls at the very top of the building, four of which are 12 feet tall and the great horned owl, at 20 feet tall, displaying its 20-foot wingspan at the main entrance. Grab a book from the shelves and take it to the Winter Garden on the ninth floor, where natural light shines through its glass roof.

89. Sneak a peek backstage at the Lyric Opera House

Tour the Lyric Opera House, including a visit to the orchestra pit and backstage where the pros bring the stage to life during a one-hour tour located within the Civic Opera Building, a historic art deco skyscraper.

90. Watch butterflies take their first flights at the Peggy Notebaert Museum

More than 1,000 butterflies that make up 40 species fly freely in this museum’s 2,700 square-foot greenhouse. In addition to learning about the life cycle from caterpillar to butterfly, visitors can watch newly-emerged butterflies take their first flight daily.

91. Don’t miss the National Museum of Mexican Art’s gift shop

First, this art museum is located in Pilsen which is almost like an art museum in itself since the neighborhood is filled with beautiful murals. Then, the museum, which offers free admission, features Mexican, Latino and Chicano art. Finally, the gift shop, Tienda Tzintzuntzán: Place of the Hummingbird, feels like its own little museum but even better since you can take a piece of art with you!

92. Visit the country’s first independent museum dedicated to Africans and Americans of African descent

Most people know of the National Museum of African American History and Culture in Washington, D.C., but may not know about the DuSable Museum of African American History in Washington Park. The first independent museum dedicated to the collection, preservation and study of the history and culture of Africans and Americans of African descent, the facility includes permanent and rotating exhibits and often hosts films, children’s events and literary discussions.

93. Retreat and relax in the salt caves

For just $15 a session, you can lie on a beach chair, close your eyes and let the salt caves at Galos Caves do their work. Relaxing might be harder during peak times when kids might be around, too, so choose your time wisely.

94. Relax among the Garden of the Phoenix at Jackson Park

If being out in nature is more your speed, head to the calming and gorgeous Osaka Garden, also known as the Garden of the Phoenix, the Japanese garden on Jackson Park’s Wooded Island. Enjoy walking the path and footbridges and listening to the cascading waterfall in this scenic sanctuary.

95. Browse the indie bookstores

Semicolon Books, Chicago, IL

Photo courtesy of Megy Karydes

There’s no shortage of amazing independently-owned bookstores in Chicago, including Women & Children’s First, Semicolon, Volumes, Quimby’s, Sandmeyer’s, Madison Street Books and The Underground Bookstore. Talk with the proprietors and you may find your next favorite author.

96. Attend the Printers Row Lit Fest

Hundreds of authors, from household names to those debuting, present and sign books at this annual event of literary note. Many schedule their weekend to hit up the book fest in Printers Row and then walk to enjoy some live Chicago Blues at the annual Blues Fest in Millennium Park.

97. Don’t miss the annual Newberry Library Used Book Fair

Bibliophiles have this event on their calendar as soon as the dates are announced (hint: late July). An estimated 120,000 books in 70 categories are available, most of which are $3 or less.

98. Go inside to see outsider art

Intuit: The Center for Intuitive and Outsider Art is dedicated to the work of those who are self-taught or have had little influence from the mainstream art world. In addition to rotating exhibits, the Henry Darger Room, which includes works from Chicago’s most famous outsider artist.

99. Explore the work of female-identified artists

Woman Made Gallery began in 1992 to support, cultivate and promote the work of women and female-identifying artists. Since its inception, it’s exhibited the work of more than 8,250 artists. Visit the gallery throughout the year as it hosts rotating exhibits.

100. Eat a burger at the Goat

Not many restaurants can claim a “Saturday Night Live” skit but, then again, the original Billy Goat Tavern is something out of the ordinary. What was once the hangout for many Chicago Tribune reporters since it’s in close proximity to the Tribune Tower (and hidden down the stairs to the lower level of Michigan Avenue to get to it), Billy Goat is still best known for its alleged curse on the Chicago Cubs.

101. Test your vertical leap against Michael Jordan

Want to compare your wingspan to that of Scottie Pippen, test your vertical leap against Michael Jordan or check out the largest collection of Chicago Cubs World Series memorabilia in Chicago? Head to the Chicago Sports Museum, located on Level 7 of Water Tower Place.

So much more

There are so many things to do in Chicago — so much to do, eat, drink, explore, discover, walk, bike and more — that it’s impossible to cram it all in one list. This list of 101 best things to do in Chicago should keep you busy, whether you’re visiting the Windy City or live here.

And don’t forget there are more things to do in Chicago than enjoy our deep dish pizza (although Chicago does have plenty of great pizza, too!).

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Megy KarydesAs a Chicago-based freelance writer, Megy Karydes has covered everything from space-aged tomato seeds grown in a Chicago Public School to Chicago Blues musician Lurrie Bell. Her work has been featured in USA Today, Travel + Leisure, Midwest Living magazine and other national and regional media outlets. When she's not out exploring the city with her two children and husband, she's perfecting her air hockey technique.

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