Visitors may enjoy a variety of activities and sights in the dynamic and diverse city of Chicago. There is always plenty to see and do in the Windy City, from top-notch museums and galleries to stunning architecture, picturesque parks, and a flourishing food scene.

Overall, Chicago is a great location for anyone wishing to experience the finest of city living because it has so many fun things to do and see for tourists to enjoy. Learn about the top activities in Chicago, including famous dishes, scenic vistas, cultural must-sees, and late-night fun.

1. Eye masterpieces at the Art Institute of Chicago

The Art Institute of Chicago is home to a permanent collection of more than 300,000 works of art, which is protected by a famous pair of bronze lions.

From Georges Seurat’s famous painting A Sunday on La Grande Jatte—famous for appearing in Ferris Bueller’s Day Off—to Andy Warhol’s photograph of actress Elizabeth Taylor, the Art Institute of Chicago is brimming with masterpieces from every age. Visit “Salvador Dal: The Image Disappears” this month to view more than 30 works of art by Spanish surrealist Salvador Dal, including paintings, sketches, photographs, and surrealist objects.

The Thorne Miniature Room, tucked away in the Art Institute’s basement, features 68 1:12 size recreations of American, European, and Asian buildings and furnishings. It’s comparable to the kind of incredibly realistic, highly detailed doll house you wish you had as a child.

2. Find serenity at the Garfield Park Conservatory

A stunning glass building with more than 100,000 plants.

There aren’t many better spots in Chicago to escape the cold when the temperatures drop than the eight indoor display gardens at Garfield Park Conservatory. Admire 65-foot Palm House’s towering tropical plants, cacti in the Desert House, and lush ferns in the Fern Room as you picture Illinois’ prehistoric past.  

From Friday through Sunday, stop into Horticulture Hall for a cold brew brewed with lavender, oat milk, and espresso by Monday Coffee Co., the conservatory’s on-site coffee pop-up.

3. Tap your toes to late-night jazz at the Green Mill

An Uptown institution that carefully selects free jazz and sophisticated bebop performances.

Al Capone and other Chicago gangsters were known to attend the Green Mill in the 1920s, but since the repeal of Prohibition, the venue has developed a reputation for featuring live jazz every night.

Photographing the gleaming marquee, which Michael Mann’s 1981 neo-noir film Thief didn’t actually ruin.

4. Root, root, root for the home team at Wrigley Field

Possibly the most well-known and stunning location in the city to watch a baseball game

The Friendly Confines, which have been associated with the North Side for more than a century, have been slightly renovated over time. In 1988, it finally caved and installed lights; a few years before, a jumbotron was built in left field. But regardless of whether the Cubbies win or lose, this stadium will always be packed with fans thanks to the ivy that covers the outfield walls, the manual scoreboard, and other vintage magnificence.

Purchase inexpensive(ish) general admission bleacher tickets for the best Wrigley Field experience. 

5. See a blockbuster movie at Alamo Drafthouse

A well-known network of theatres from Texas.

The theatre offers a wide variety of food and drink options, and servers will bring meals to patrons’ seats while movies are being shown.

The theatre hosts a variety of special events, such as boisterous screenings where conversation is encouraged and movie parties, immersive watching experiences with entertaining props, themed drinks, and more.

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6. Hang out with a mummy at Field Museum

A huge natural history museum built to hold the biological and anthropological collections for the World’s Columbian Exposition of 1893.

Making a decision about what to view at the Field Museum can be challenging with its 350,000 square feet of permanent exhibition space. Starting there will allow you to descend inside a replica of the 5,000-year-old tomb of the pharaoh’s son Unis-Ankh, which is located in the institution’s well-known “Inside Ancient Egypt” display. From there, you can explore a sizable collection of Egyptian artifacts, including one of the biggest U.S. collections of mummies.

Explore the mysterious process of dying at the exhibit “Death: Life’s Greatest Mystery,” which looks at death via a number of natural an

7. See a stellar play from the Steppenwolf Theatre

What comes to mind after hearing “Chicago theatre”.

Steppenwolf is renowned for its stellar ensemble of performers. (Folks like Laurie Metcalf, John Malkovich and Tracy Letts number among its ranks).

In the novel “Last Night and the Night Before,” a mother and daughter who are on the run unexpectedly show up at their family’s home.

8. Explore the universe at the Adler Planetarium

An institution devoted to astronomy and all things celestial.

With exhibitions on the first lunar expeditions, the solar system, and more, along with immersive performances in the dome theater, you may leave the world. The greatest public telescope in the region is located at the Doane Observatory and can collect 7,000 times more light than the human eye can.

Every Wednesday from 4–10 p.m., Adler at Night is the planetarium’s after-hours programme. The best part is that Illinois residents can enter for free.

9. Travel across an elevated trail on the 606

An elevated railroad track that was once abandoned and was given the name of the first three numbers of each Chicago zip code.

In search of a quick route connecting Logan Square, Humboldt Park, Wicker Park, and Bucktown? That’s it. The city cleaned up the 2.7-mile path and transformed it into a useful attraction that both residents and tourists enjoy.

Conagra Mural (Urbs in Horto), a colourful work by nearby artist Jeff Zimmermann that honours Chicago’s agricultural heritage, is located just across the Milwaukee Avenue bridge.

10. Make a pit stop at the Chicago Cultural Center

This magnificent structure, which is the nation’s first free municipal cultural center, is situated just around the corner from Millennium Park. Inside, you’ll find a tonne of programming, exhibitions, and stunning architectural flourishes to explore, as well as a gift shop filled with items made by local artists.

Visitors to the Loop should make a point to check out any active programmes at the Cultural Center, which can range from large-scale architecture expos to art exhibitions. Did we also mention that it is totally free?

Visit the 38-foot Tiffany glass dome in Preston Bradley Hall and then proceed to the Landmarks Gallery on the first level to view “The Great Chicago Fire in Focus,” an exhibition of photographs depicting the destruction of the historic disaster.

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11. Get acquainted with Frank Lloyd Wrights’s architecture at the Robie House

A famous home that Frank Lloyd Wright referred to as “the cornerstone of modern architecture.”

Although nearby Oak Park is a haven for fans of Frank Lloyd Wright, you can view some of the architect’s best creations inside the city. Wright’s distinctive Prairie School design can be seen in both the outside and inside of the Robie House in Hyde Park. A tour of the historic home is available five days a week, hosted by the Frank Lloyd Wright Trust, where you may also gain some decorating inspiration.

Beautiful art glass windows aplenty, as well as furniture (also designed by Wright)

12. Go back in time at the Historic Pullman Foundation Exhibit Hall

This location has exhibits about the development and preservation of the South Side neighbourhood.

Businessman George Pullman created an entire village to house his workers when he opened a train sleeper car manufacturing on Chicago’s South Side. The Pullman Foundation Exhibit Hall is the ideal site to begin exploring the industrial complex, which has now been named a National Monument.

Set out on a self-guided tour of the area to see the famous structures that have appeared in movies like The Fugitive and Road to Perdition.

13. Grab a cocktail under glowing red lights at the California Clipper

A well-liked Humboldt Park bar that reopened in 2022 after a two-year hiatus.

When The Clipper closed in early 2020 due to a rent disagreement, its future seemed in jeopardy, but don’t worry—Orbit Group, the bar’s new owners, haven’t done much to alter the location aside from a few modest decorating modifications.

With a selection of DJ nights, “The Little Clip,” a dance lounge that occupies the former C.C. Ferns location, pays homage to Danny’s, the long-gone Bucktown pub where some of the Clipper’s current crew once worked.

14. Watch the Chicago Symphony Orchestra perform

A well-known orchestra worldwide.

The CSO, regarded as one of the best and oldest orchestras in the country, performs a wide range of captivating music and also welcomes soloists and small ensembles on tour. You can see spectacular performances that are timed to the music from well-known movies like Star Wars and Harry Potter. The CSO resides at Symphony Center from fall through spring.

The Chicago Symphony Orchestra (CSO) sets up shop in Highland Park’s Ravinia Festival during the summer.

15. Get high at 360 Chicago

This observatory, located 1,030 feet above the streets atop the structure formerly known as the John Hancock Center, provides views of the city (and neighbouring states).

Whether you are a native or tourist to Chicago, the views from the 94th level are unrivalled. Stay on site to sip a glass at the 360 CHICAGO bar or check out some of the interactive displays illuminating the history of the city.

The most horrifying attraction at 360 CHICAGO is TILT. Visitors board a platform made of glass that progressively tilts over the building’s side at a 30-degree angle. Those looking for an adrenaline rush will want to pay the higher ticket price.

16. Catch a foul ball at Guaranteed Rate Field

Formerly (and, to some, still) known as Comiskey Park, this place serves as the Chicago White Sox’s home field. 

Okay, so the South Side squad doesn’t have the same passionate fanbase as its northern neighbours. (although the whole city went nuts when it clinched the World Series in 2005). However, the venue is significantly larger than Wrigley, and it’s virtually always able to walk up and buy tickets.

A foot-long, half-pound hot dog topped with Champagne Vidalia relish and jalapeño mustard is available, or you can indulge in a Rainbow Cone to fulfil your sweet taste.

17. Catch rising bands at the Empty Bottle

The finest rock venue in the United States.

A performance at the Empty Bottle has been a rite of passage for both local and visiting musicians for more than 25 years. Despite having a capacity of only about 300, the unassuming club on the outskirts of Ukrainian Village is a good place to catch up-and-coming rockers, electronic groups, and experimental musicians. Grab an Old Style, locate a position on the steps next to the stage, and enjoy a show that is certain to be memorable.

A slice of pizza at the Pizza Friendly Pizza next door before (or after) the performance

18. Laugh it up at a comedy show

The Second City, a famous comedy club in Chicago.

Bill Murray, Tina Fey, Chris Farley, Steve Carell, and other well-known comedians all got their start in the business thanks to the face of the local comedy scene. Any night of the week, you may witness an improv or sketch show by up-and-coming performers.

19. Take a stroll through Chinatown

A district that is one of the main centres of the Chinese community in Chicago and is home to many eateries, stores, and stunning examples of East Asian architecture.

If you enjoy being outside, Chinatown is a terrific spot to do it. You can stroll through Chinatown Square or take in the expansive views of the skyline from Ping Tom Memorial Park.

The list includes umplings from QYX, bubble tea from Joy Yee’s walk-up window, Peking duck from BBQ King House, cocktails from Nine Bar, and more. Work your way south along Wentworth starting at Chinatown Square, crossing the street’s renowned gate and entering its main commercial district.

20. Get down to house music at Smart Bar

A great spot to get lost in house music is in the city where it was created.

Chicago was the birthplace of a new sound in the 1980s that still has an impact on contemporary hip-hop and electronic music. There is no more genuine setting than Smart Bar to experience house music. Skilled DJs, drag artists, and sweaty partygoers congregate inside the underground Wrigleyville club to the steady beat of a house beat.

The jam-packed Queen dance celebration that happens almost every Sunday night.

21.  Hear live blues at Kingston Mines

When in Chicago, you must listen to blues music, and Kingston Mines is one of the best sites to experience the blues.

High-energy live blues bands perform on two stages at the largest and longest-running blues club in the city until 4 a.m. on Thursdays and Fridays and 5 a.m. on Saturdays. It’s difficult to have a bad night here, whether you’re mingling with sleepy tourists from Iowa or pals of the local blues musicians performing on stage.

You are given access to both rooms and their two distinct stages by the cover.

22. Cheer on the Bulls and Blackhawks at the United Centre

A venue for high-profile pop performances as well as professional basketball and hockey.

Although you may still take a photo in front of Michael Jordan’s statue in the United Center’s public atrium, the West Side arena no longer has regular games featuring the basketball legend. The Bulls and the Blackhawks, two of the biggest professional sports teams in the city, call the arena home during the basketball and hockey seasons. Major pop and rock concerts, with performers like U2, Drake, and Madonna, are also held there.

The venue has teamed up with neighbourhood eateries like Honey Butter Fried Chicken and Lillie’s Q to serve food and beverages that vastly beyond standard stadium fare.  

23. Sip suds at Half Acre Brewery Balmoral

The majority of the beer produced by one of the city’s main brewers is stored at a warehouse on the extreme North Side.

The sizable parking lot at Half Acre Balmoral provides space to enjoy specialty beers like Daisy Cutter and Tome outside. For hungry drinkers, a variety of bar snacks is also offered.

Be on the lookout since there are beers on tap that are just available here.

24. Go mini-golfing (and drinking) at Puttery

A cocktail bar with mini-golf.

Go mini golfing at this innovative concept if the weather isn’t conducive to hitting the links outside. Puttery, a 23,000 square foot facility, has two themed courses and cutting-edge equipment including trackable balls and digital scorecards.

After you’ve finished playing, relax by lounging in the posh lounge area. There is a wide selection of approachable snacks and creative beverages.

25. Walk through an outdoor art gallery at the 16^th Street Murals

An old railway embankment in Pilsen that spans from the Chicago River to Western Avenue is covered in a mix of murals and street art.

As you go down 16th Street, you’ll see murals created by both domestic and foreign artists, like The Yok and Sheryo, as well as local painters JC Rivera and Hebru Brantley.

Just west of 16th and Laflin Street is the famed painting of a severed possum by Belgian street artist ROA.

Conclusion

Overall, Chicago is a lively, diversified city with a wide range of intriguing attractions, including world-class museums and cultural institutions, sports and entertainment facilities, lovely parks and gardens, and historic buildings. So take a break from the everyday hustle and enjoy your time in Chicago.

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