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26 places to go in Chicago this winter

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

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Low temperatures don’t stop Chicagoans from taking advantage of all the city has to offer. And if you’re visiting, trust us, it’s worth it to brave the cold. Winter is just as spectacular as the other seasons.

Chicago 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.

[Note: Map is listed in geographic order]

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1. Baha'i House of Worship

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

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. The Green Mill

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4802 N Broadway
Chicago, IL 60640

It’s hard to miss the Green Mill’s flashy, neon sign. The Uptown cocktail lounge originally opened in 1907 and its name pays tribute to the well-known Moulin Rouge (meaning Red Mill) of Paris. It is known for jazz performances, poetry slams, and its connections to Chicago gangster Al Capone. Head here to be transported back to the ’30s and ’40s club scene amidst the Art Deco decor.

3. Music Box Theatre

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

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.

4. Wrightwood 659

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

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. Through January, the museum will be setting up for its February exhibitions. It will feature a show in conjunction with the Smart Museum, “The Allure of Matter”, focusing on contemporary Chinese designers. Wrightwood will also bring back a popular exhibit covering the architect Tadao Ando’s most notable work.

5. The Hideout

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1354 W Wabansia Ave
Chicago, IL 60642
(773) 227-4433
Visit 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.” In addition to music, the venue hosts live podcasts, interviews, and fundraisers like Soup & Bread.

6. Museum Of Contemporary Art Chicago

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

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 open through winter 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. Frank Lloyd Wright Home and Studio

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

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.

8. Garfield Park Conservatory

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

A greenhouse at Garfield Park Conservatory in Chicago. There is a red path surrounded by plants. The walls and ceiling are glass.

9. Chicago Cultural Center

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78 E Washington St
Chicago, IL 60602
(312) 744-6630
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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. While the Chicago Architecture Biennial is over, there are many other happenings through winter. The University of Chicago hosts a lecture series here, there’s a Latino film festival, and a kids music program.

10. Maggie Daley Park

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337 E Randolph Service St
Chicago, IL 60601
(312) 742-3918
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The 20-acre downtown park was completed in 2014 and designed by the premier landscape architect Michael Van Valkenburgh. Enter through Grant Park and cross over the winding, snake-like pedestrian bridge into playgrounds, winding pathways, rock climbing walls, an ice-skating ribbon, tennis courts, and gardens. Here, you’ll get some of the best views of the downtown skyline, too.

11. The Art Institute of Chicago

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

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.

12. Willis Tower Skydeck

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

After a recent renovation, the entrance to Willis Tower is quite different. There’s a new food hall, fancy new elevators, and a new cloud-like art installation. However, the main attraction at the iconic tower is the Skydeck. On a good day, you can see how the city has radiated out and developed. While the building isn’t the tallest anymore, the 103rd floor observatory still holds the distinction of highest observation deck in the United States.

13. Lakefront Trail

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Lakefront Trail
Chicago, IL

The 18-mile Lakefront Trail is one of the best ways to enjoy Chicago, even in winter. For one, you’ll be able to find some peace and quiet (during the summer the trail is packed). When it gets cold enough, you might find twisty ice sculptures formed by the wind and Lake Michigan waves. There are separate bike and pedestrian lanes, nature preserves, parks, and beaches all along the lakefront.

14. Harold Washington Library

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Harold Washington Library, 400 S State St
Chicago, IL 60605

The Harold Washington Library on the southern end of the Loop isn’t just the anchor of the Chicago Public Libraries system, but it’s also one of the city’s finest examples of postmodern architecture. It’s a wild building with elaborate cornices with five 12-foot owls, striking red brick, enormous arched windows, and an impressive skylight. Head up to the ninth floor for the Winter Garden, an enclosed sunlit atrium.

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15. Auditorium Theatre

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

The Auditorium Theatre is one of a kind. It was built in 1889 by architects Louis Sullivan and Dankmar Adler (who were mentoring a young Frank Lloyd Wright at the time). The building is remarkable for its construction, elaborate detail, and acoustic perfection. 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. Jane Addams Hull-House Museum

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800 S Halsted St
Chicago, IL 60607
(312) 413-5353
Visit Website

The Hull House serves as a memorial to Jane Addams, a social reformer who worked to improve the lives of immigrant Chicagoans and develop a vision of supportive settlement housing. The museum is housed in two of the settlement’s original buildings: the Hull Home and the dining hall. Here you’ll find histories of the Hull-House Settlement and how they connect to modern social justice issues of housing and immigration. Throughout the week there are free tours scheduled, one of which covers the vernacular architecture and the design of the 12-building settlement.

17. Adler Planetarium

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1300 S Lake Shore Dr
Chicago, IL 60605
(312) 922-7827
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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 Art Deco building isn’t just about the sky—looking back at the city from this far out is pretty spectacular too.

18. Soldier Field

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

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End of our tour of Soldier Field. #oldmeetsnew

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19. Glessner House

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1800 S Prairie Ave
Chicago, IL 60616

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.

20. National Museum of Mexican Art

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1852 W 19th St
Chicago, IL 60608
(312) 738-1503
Visit Website

Located in the heart of Chicago’s vibrant Pilsen neighborhood, this free museum focuses on Mexican, Latino from the past 3,000 years. The museum’s mission is to explore Latino art and history “sin fronteras” (without borders) and features a permanent collection approximately 10,000 objects as well as rotating temporary exhibits.

21. Chinatown Branch, Chicago Public Library

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2100 S Wentworth Ave
Chicago, IL 60616
(312) 747-8013
Visit Website

Chinatown’s oval-shaped public library opened in 2015 and has quickly become a neighborhood landmark. Designed by Skidmore, Owings, & Merrill, the structure sports dramatic vertical fins and a clear glass curtain wall that creates a lantern-like appearance at night. Drawing inspiration from the immediate community, the 16,000-square-foot building references traditional Feng Shui design cues throughout its interior. More than just a place to check-out books, the library also acts as an information hub for anyone looking to learn more about Chicago’s charismatic and growing Chinatown community.

22. Morton Arboretum Visitor Center

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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 folklore which kids can hunt for through the trees.

23. DuSable Museum of African American History

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

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.

The interior of a room at the DuSable Museum of African American History. There is a mural with faces. Other works of art are on the walls. Carmen Troesser

24. Frederick C. Robie House

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

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 tours as well as other special programs from the nonprofit Frank Lloyd Wright Trust.

25. Stony Island Arts Bank

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

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.

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26. South Shore Cultural Center

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

After the former country club experienced a decline, the Chicago Park District purchased the estate for about $9.8 million in 1975. For the first time, stucco-clad Mediterranean Revival building was able to show off its Classical plaster details and grand crystal chandeliers to the general public. The landmark represents a style of architecture that is rare in Chicago and so in the same year it sold to the city, it also listed on the National Register of Historic Places. The venue now houses art and dance studios, a gallery, a golf course, gardens, a beach, and a banquet hall.

1. Baha'i House of Worship

100 Linden Ave, Wilmette, IL 60091

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.

100 Linden Ave
Wilmette, IL 60091

2. The Green Mill

4802 N Broadway, Chicago, IL 60640

It’s hard to miss the Green Mill’s flashy, neon sign. The Uptown cocktail lounge originally opened in 1907 and its name pays tribute to the well-known Moulin Rouge (meaning Red Mill) of Paris. It is known for jazz performances, poetry slams, and its connections to Chicago gangster Al Capone. Head here to be transported back to the ’30s and ’40s club scene amidst the Art Deco decor.

4802 N Broadway
Chicago, IL 60640

3. Music Box Theatre

3733 N Southport Ave, Chicago, IL 60613

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.

3733 N Southport Ave
Chicago, IL 60613

4. Wrightwood 659

659 W Wrightwood Ave, Chicago, IL 60614

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. Through January, the museum will be setting up for its February exhibitions. It will feature a show in conjunction with the Smart Museum, “The Allure of Matter”, focusing on contemporary Chinese designers. Wrightwood will also bring back a popular exhibit covering the architect Tadao Ando’s most notable work.

659 W Wrightwood Ave
Chicago, IL 60614

5. The Hideout

1354 W Wabansia Ave, Chicago, IL 60642

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.” In addition to music, the venue hosts live podcasts, interviews, and fundraisers like Soup & Bread.

1354 W Wabansia Ave
Chicago, IL 60642

6. Museum Of Contemporary Art Chicago

220 E Chicago Ave, Chicago, IL 60611

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 open through winter 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.

220 E Chicago Ave
Chicago, IL 60611

7. Frank Lloyd Wright Home and Studio

951 Chicago Ave, Oak Park, IL 60302

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.

951 Chicago Ave
Oak Park, IL 60302

8. Garfield Park Conservatory

300 N Central Park Ave, Chicago, IL 60624
A greenhouse at Garfield Park Conservatory in Chicago. There is a red path surrounded by plants. The walls and ceiling are glass.

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.

300 N Central Park Ave
Chicago, IL 60624

9. Chicago Cultural Center

78 E Washington St, Chicago, IL 60602

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. While the Chicago Architecture Biennial is over, there are many other happenings through winter. The University of Chicago hosts a lecture series here, there’s a Latino film festival, and a kids music program.

78 E Washington St
Chicago, IL 60602

10. Maggie Daley Park

337 E Randolph Service St, Chicago, IL 60601

The 20-acre downtown park was completed in 2014 and designed by the premier landscape architect Michael Van Valkenburgh. Enter through Grant Park and cross over the winding, snake-like pedestrian bridge into playgrounds, winding pathways, rock climbing walls, an ice-skating ribbon, tennis courts, and gardens. Here, you’ll get some of the best views of the downtown skyline, too.

337 E Randolph Service St
Chicago, IL 60601

11. The Art Institute of Chicago

111 S Michigan Ave, Chicago, IL 60603

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.

111 S Michigan Ave
Chicago, IL 60603

12. Willis Tower Skydeck

233 S Wacker Dr, Chicago, IL 60606

After a recent renovation, the entrance to Willis Tower is quite different. There’s a new food hall, fancy new elevators, and a new cloud-like art installation. However, the main attraction at the iconic tower is the Skydeck. On a good day, you can see how the city has radiated out and developed. While the building isn’t the tallest anymore, the 103rd floor observatory still holds the distinction of highest observation deck in the United States.

233 S Wacker Dr
Chicago, IL 60606

13. Lakefront Trail

Lakefront Trail, Chicago, IL

The 18-mile Lakefront Trail is one of the best ways to enjoy Chicago, even in winter. For one, you’ll be able to find some peace and quiet (during the summer the trail is packed). When it gets cold enough, you might find twisty ice sculptures formed by the wind and Lake Michigan waves. There are separate bike and pedestrian lanes, nature preserves, parks, and beaches all along the lakefront.

Lakefront Trail
Chicago, IL

14. Harold Washington Library

Harold Washington Library, 400 S State St, Chicago, IL 60605

The Harold Washington Library on the southern end of the Loop isn’t just the anchor of the Chicago Public Libraries system, but it’s also one of the city’s finest examples of postmodern architecture. It’s a wild building with elaborate cornices with five 12-foot owls, striking red brick, enormous arched windows, and an impressive skylight. Head up to the ninth floor for the Winter Garden, an enclosed sunlit atrium.

Harold Washington Library, 400 S State St
Chicago, IL 60605

15. Auditorium Theatre

50 Ida B. Wells Dr, Chicago, IL 60605

The Auditorium Theatre is one of a kind. It was built in 1889 by architects Louis Sullivan and Dankmar Adler (who were mentoring a young Frank Lloyd Wright at the time). The building is remarkable for its construction, elaborate detail, and acoustic perfection. If you can’t see a performance in the rich space, there are a few tours throughout the week where you can learn more.

50 Ida B. Wells Dr
Chicago, IL 60605

16. Jane Addams Hull-House Museum

800 S Halsted St, Chicago, IL 60607

The Hull House serves as a memorial to Jane Addams, a social reformer who worked to improve the lives of immigrant Chicagoans and develop a vision of supportive settlement housing. The museum is housed in two of the settlement’s original buildings: the Hull Home and the dining hall. Here you’ll find histories of the Hull-House Settlement and how they connect to modern social justice issues of housing and immigration. Throughout the week there are free tours scheduled, one of which covers the vernacular architecture and the design of the 12-building settlement.

800 S Halsted St
Chicago, IL 60607

17. Adler Planetarium

1300 S Lake Shore Dr, Chicago, IL 60605

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 Art Deco building isn’t just about the sky—looking back at the city from this far out is pretty spectacular too.

1300 S Lake Shore Dr
Chicago, IL 60605

18. Soldier Field

1410 Museum Campus Dr, Chicago, IL 60605

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.

1410 Museum Campus Dr
Chicago, IL 60605

19. Glessner House

1800 S Prairie Ave, Chicago, IL 60616

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.

1800 S Prairie Ave
Chicago, IL 60616

20. National Museum of Mexican Art

1852 W 19th St, Chicago, IL 60608

Located in the heart of Chicago’s vibrant Pilsen neighborhood, this free museum focuses on Mexican, Latino from the past 3,000 years. The museum’s mission is to explore Latino art and history “sin fronteras” (without borders) and features a permanent collection approximately 10,000 objects as well as rotating temporary exhibits.

1852 W 19th St
Chicago, IL 60608

21. Chinatown Branch, Chicago Public Library

2100 S Wentworth Ave, Chicago, IL 60616

Chinatown’s oval-shaped public library opened in 2015 and has quickly become a neighborhood landmark. Designed by Skidmore, Owings, & Merrill, the structure sports dramatic vertical fins and a clear glass curtain wall that creates a lantern-like appearance at night. Drawing inspiration from the immediate community, the 16,000-square-foot building references traditional Feng Shui design cues throughout its interior. More than just a place to check-out books, the library also acts as an information hub for anyone looking to learn more about Chicago’s charismatic and growing Chinatown community.

2100 S Wentworth Ave
Chicago, IL 60616

22. Morton Arboretum Visitor Center

Lisle, IL 60532

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 folklore which kids can hunt for through the trees.

23. DuSable Museum of African American History

740 E 56th Pl, Chicago, IL 60637
The interior of a room at the DuSable Museum of African American History. There is a mural with faces. Other works of art are on the walls. Carmen Troesser

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.

740 E 56th Pl
Chicago, IL 60637

24. Frederick C. Robie House

5757 S Woodlawn Ave, Chicago, IL 60637

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 tours as well as other special programs from the nonprofit Frank Lloyd Wright Trust.

5757 S Woodlawn Ave
Chicago, IL 60637

25. Stony Island Arts Bank

6760 S Stony Island Ave, Chicago, IL 60649

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.

6760 S Stony Island Ave
Chicago, IL 60649

26. South Shore Cultural Center

7059 S South Shore Dr, Chicago, IL 60649

After the former country club experienced a decline, the Chicago Park District purchased the estate for about $9.8 million in 1975. For the first time, stucco-clad Mediterranean Revival building was able to show off its Classical plaster details and grand crystal chandeliers to the general public. The landmark represents a style of architecture that is rare in Chicago and so in the same year it sold to the city, it also listed on the National Register of Historic Places. The venue now houses art and dance studios, a gallery, a golf course, gardens, a beach, and a banquet hall.

7059 S South Shore Dr
Chicago, IL 60649