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26 things to do in Chicago this fall

26 things to do in Chicago this fall

These are the places that you must visit in Chicago right now—new classics, old favorites, and other essential sites

By Sara Freund and Jay Koziarz Updated Sep 23, 2019, 3:54pm CDTFall trees in Grant Park. | Photo by Shutterstock

Chicago in the fall is beautiful: crisp air on the lakefront, incredible fall colors in historic parks, and plenty of festive neighborhood happenings.

It is a sprawling city of neighborhoods with stunning architecture, world-class museums, cultural hot spots, and off-the-path hidden gems. Between its iconic landmarks and the new attractions that regularly pop up exploring Chicago can be overwhelming, especially if you’re traveling with kids or you’ve recently moved here.

So, we’re here to help with this seasonal guide to our city. From museums, parks, skyscrapers, and theaters, we’ve identified 26 places worth exploring.

If we’ve missed something—a neighborhood favorite, an amazing landmark, or anything else—drop us an email.

1. Baha'i House of Worship

100 Linden Ave Wilmette, IL 60091 (847) 853-2300

The Bahai Temple is one of ten in the world and is the oldest house of worship for the faith. Architect Louis Bourgeois designed the highly detailed structure for the Bahai in 1903 which features a 138-foot dome covered in lace-style carvings surrounded by gardens and a pool. Symbols of many religions are etched into the pillars’ intricate patterns including a crescent moon, a Star of David, and a cross. A sacred number for Bahai is nine, which was incorporated into the architecture and design—there are nine pillars, nine entrances, nine fountains, and nine-pointed stars.

2. Music Box Theatre

3733 N Southport Ave Chicago, IL 60613 (773) 871-6604

Built in 1929, the Music Box is one of only a handful of Chicago’s original movie houses to survive through the decades relatively unchanged. The main auditorium features whimsical Mediterranean-inspired architecture under a simulated inky night sky complete with twinkling stars and projected clouds. The Lakeview destination is one of the city’s top venues for enjoying foreign, independent, experimental, and classic cinema hosts a number of film festivals each year.

3. Wrightwood 659

659 W Wrightwood Ave Chicago, IL 60614(773) 437-6601

The Tadao Ando-designed exhibition space sits right in the middle of a residential street in Lincoln Park. The facade, 1920s brick with a Greek revival flare, alludes to its former life as apartments but inside is Ando’s masterful concrete work and thoughtful consideration of light. The shows focus on architecture, design, and socially engaged art. Until December 14, the site will be showing Ando’s most famous gallery and museum designsas part of an exhibit connected with the Chicago Architecture Biennial.

4. Alfred Caldwell Lily Pool

125 W Fullerton Pkwy Chicago, IL 60614(773) 883-7275Visit Website

Hidden in plain sight behind a Prairie School-style gate on Fullerton Parkway, this often overlooked Lincoln Park treasure was originally part of a larger Victorian garden conceived by landscape architect Alfred Caldwell in 1889. The pond fell into disrepair, but after a $2.4 million renovation in 2002 it’s a pleasant oasis with birds and native plants. Make sure to see the fall foliage before the park closes in mid-November.

5. The Hideout

1354 W Wabansia Ave Chicago, IL 60642(773) 227-4433Visit Website

The Hideout opened in 1934 in a 100-year-old, balloon-frame house as a bar for everyday folk, and now is an institution beloved by devoted music misfits. Its name wasn’t chosen, but given by its patrons. The music venue is best described with its own words: “A clandestine destination with a guaranteed good time,” and “the last hold-out of the rebel club.”


6. Museum Of Contemporary Art Chicago

220 E Chicago Ave Chicago, IL 60611(312) 280-2660

Located one block east of the historic Water Tower, Chicago’s MCA is one of the world's largest contemporary art venues. It also has a stylish restaurant, Marisol, a popular design-focus gift shop, and a peaceful outdoor courtyard. Two notable exhibits opening this fall include “The Shape of the Future” which examines modernist disasters, dreams, and histories of the built environment and “Routes and Territories” which looks at stories of human migration.


7. Poetry Foundation

61 W Superior St Chicago, IL 60654(312) 787-7070

Located in River North, the library of the Poetry Foundation contains 30,000 volumes of text, audio and video recordings, and other poetry-related materials. Opened in 2011, the ultra-modern structure sports a tree-filled courtyard wrapped by a perforated metal screening. “There are aspects of the building that are very much like a poem,” said architect John Ronan regarding the design. “It’s not a building that’s a one-liner. It’s not something you see right away. You might have to go back to it two or three times.”

8. Frank Lloyd Wright Home and Studio

951 Chicago Ave Oak Park, IL 60302(312) 994-4000

Oak Park’s Frank Lloyd Wright Home and Studio is a must-see site for fans of the famous architect and his influential Prairie School of design. Operated by the Frank Lloyd Wright Trust, the museum offers regular guided tours and serves as a starting point for walking tours of the surrounding Oak Park historic district. Beginning this fall, there will be drinks and live music in the evenings.

9. Garfield Park Conservatory

300 N Central Park Ave Chicago, IL 60624(312) 746-5100

Plans for the 4.5-acre horticultural oasis began in 1905 with the lofty goal of creating with world’s largest publicly owned conservatory. Six greenhouses and two exhibition halls, which host annual flower shows, were designed by Danish-American landscape architect Jens Jensen and the firm Schmidt, Garden, & Martin. One of the most popular rooms of the conservatory, the Palm House, features a double coconut palm first grown by employees in 1959. Over in the Aroid House, you’ll find yellow glass Persian Lillies crafted by artist Dale Chihuly in the pond.

10. Chicago Cultural Center

78 E Washington St Chicago, IL 60602(312) 744-6630

The Chicago Cultural Center is an impressive, historic building downtown that’s free and open to the public. It was used as Chicago’s first central library in 1897 and now operates as a community space and exhibition hall. The Michigan Avenue building is currently home to the Chicago Architecture Biennial, which runs through January 5, with a total of 51 art installations. The event focuses on the lesser-told histories and stories of the built environment in Chicago and other global metropolises.

11. Maggie Daley Park

337 E Randolph Service St Chicago, IL 60601(312) 742-3918

The rock climbing wall is open until mid-November, but after that the curving ribbon transforms into an ice-skating rink. Rollerblade, play tennis, or have a picnic with an unreal view of Chicago’s best skyscrapers before the weather turns a little too brisk. Nearby is Millennium Park which is connected by a snake-like, silver bridge.

12. The Art Institute of Chicago

111 S Michigan Ave Chicago, IL 60603(312) 443-3600

The Art Institute is massive and it’ll be exhausting if you try to see it all in one day. First timers should see The Modern Wing and the Impressionist paintings, it’s one of the finest and largest collections in the world. If you’ve got a little more time, take a peek at the Chicago Stock Exchange Trading Room. The original was demolished in 1972, but the Louis Sullivan and Dankmar Adler designed room was rebuilt here in 1977 with elaborate stenciled decorations, molded plaster, and art glass—some of which was preserved and reused in this replica.

13. Willis Tower Skydeck

233 S Wacker Dr Chicago, IL 60606(312) 875-9696

The base of Willis Tower is getting an ambitious revamp, the iconic tower’s Skydeck attraction is still open for business. Guests can learn about the building’s construction in the “Reaching For The Sky” exhibit and step out onto the “ledge”—a clear box perched beyond the buildings facade. Willis (formerly Sears) long lost its title as the world’s tallest building, but its 103rd-floor observatory still holds the distinction of the highest observation deck in the United States.

14. Lakefront Trail

Lakefront Trail Chicago, IL

The 18-mile Lakefront Trail is one of the best ways to enjoy Chicago and it’ll be a little less crowded come fall. Get on a Divvy and ride along the Lake Michigan or leisurely stroll in one of the nearby parks. The open, clear lakefront is what we are known for, and it’s magnificent.

15. Auditorium Theatre

50 Ida B. Wells Dr Chicago, IL 60605(312) 341-2300

The Auditorium Theatre, built in 1889 by architects Louis Sullivan and Dankmar Adler (who were mentoring a young Frank Lloyd Wright at the time), is one of a kind. The building is remarkable for its construction, elaborate detail, and acoustic perfection. Currently, the theater is working to restore the meticulous, gold stencil work that was unfortunately painted over in previous decades. If you can’t see a performance in the rich space, there are a few tours throughout the week where you can learn more.

16. Adler Planetarium

1300 S Lake Shore Dr Chicago, IL 60605(312) 922-7827

Explore the stars, planets, and solar systems at the country’s first planetarium. The Doane Observatory has one of the largest aperture telescope available to the public and after-hours events where visitors can see the Moon, Jupiter, or Saturn. The view from the Adler isn’t just about the sky—looking back at the city from this far out is pretty spectacular too.

17. 16th Street Murals in Pilsen

W 16th St Chicago, IL

The 16th Street railroad embankment is transformed by street artists including Hebru Brantley, Sam Kirk, Chris Silva, and Amuse. What started with only a few murals is now an official initiative to bring new art to the two-mile stretch between Halsted Street and Western Avenue. There are plenty of murals outside of 16th Street too, such as Hector Duarte’s home and studio which is entirely covered in a mural and is a frequent stop on art tours in Pilsen.

18. Glessner House

1800 S Prairie Ave Chicago, IL 60616(312) 326-1480

Near South Side’s historic Prairie District, the Glessner House is an important commission—influencing the works of architects such as Louis Sullivan, Frank Lloyd Wright and Mies van der Rohe. Built in 1887, when Victorian homes were popular, the Henry Hobson Richardson design featured a courtyard and a strong visual emphasis on the horizontal. This National Historic Landmark now operates as a non-profit museum.

19. Ping Tom Memorial Park

1700 S Wentworth Ave Chicago, IL 60616(312) 225-3121

Originally a rail yard, this park is now has rolling green hills, Chinese landscape design elements, a playground, and boathouse. If you are downtown, hop on the water taxi which makes stops at the park until December 1. It’s a quick way to see the sights—although not as thorough as the Chicago Architecture River Cruise which stops running mid-October it’ll get the job done. Plus, you get to explore Chinatown, an impressive park, and nearby murals.

20. Morton Arboretum Visitor Center

Created in 1922, the Morton Arboretum grew from the original estate of Joy Morton in 1910, conservationist and founder of Chicago’s famous Morton Salt Company. Located in Lisle, Illinois (about a 30-minute drive or Metra train ride), this 1,700-acre “living museum” features native trees and rare imported species. Within the grounds is a Danish artist’s installation consisting of giant, wooden trolls from European folklorewhich kids can hunt for through the trees.

21. Promontory Point

5491 S Shore Dr Chicago, IL 60615 (312) 742-5369

This 12-acre man-made peninsula on Lake Michigan’s south shore first opened to the public in 1937. Dubbed simply “The Point” by locals, the Alfred Caldwell-designed park offers incredible views of the Chicago skyline. While most of Chicago’s lakefront retaining walls have been replaced by concrete revetments, The Point still holds on to its original uneven limestone steps—a feature residents fought to preserve. Watch day turn to night at the edge of the water or go for a stroll around the peninsula searching for fiery fall colors.

22. DuSable Museum of African American History

740 E 56th Pl Chicago, IL 60637(773) 947-0600

This museum is located within Washington Park, which is a sprawling, historic open space. At the museum, visitors can explore one of the world’s largest and oldest collections of African and African American collections, texts, histories and culture. Harold Washington, Chicago’s 42nd mayor, has a permanent exhibit about his legacy.

23. Frederick C. Robie House

5757 S Woodlawn Ave Chicago, IL 60637(312) 994-4000

If there’s any single home that perhaps best reflects architect Frank Lloyd Wright’s unique Prairie School style, it is the Frederick C. Robie House. Built in 1909 for a young industrialist, the structure—like many Wright commissions—was constructed with custom furniture, art glass windows, and other bespoke architectural details. Located on the University of Chicago’s Hyde Park campus, the building regularly features guided toursas well as other special programs from the nonprofit Frank Lloyd Wright Trust.

24. Stony Island Arts Bank

6760 S Stony Island Ave Chicago, IL 60649(312) 857-5561

Originally built in 1923, this William Gibbons Uffendell-designed bank found new purpose as a gallery, media archive, library, and community center after the Rebuild Foundation and Theaster Gates radically restored the deteriorating structure. The Stony Island Arts building is important cultural hub for the South Side—housing artists in residence, hosting Black Cinema House film screening, and providing access to notable collections. The archive contains the archive of Johnson Publishing, publisher of Ebony and Jet magazines, and over 60,000 University of Chicago glass lantern slides of art and architectural history.

25. South Shore Cultural Center

7059 S South Shore Dr Chicago, IL 60649(773) 256-0149

The landmark building and former country club sits in the middle of a 70-acre park. Take a walk through the historic building which features a solarium, formal dining hall, theater, and restaurant. Nearby there’s a nature sanctuary, butterfly garden, nine-hole golf course, a beach, and picnic space.

26. Soldier Field

1410 Museum Campus Dr Chicago, IL 60605(312) 235-7000

Soldier Field has lot more than just football happening on its field. There are concerts, soccer matches, rugby games, and many other events. The stadium offers tours where you’ll be able to get a first-hand look at the historic exterior and controversial modernist interior. Plus, the home of the Bears is right on the lakefront near museum campus with beautiful views of the downtown skyline.

Orignal artice and image sources can be found at

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