1. Dat Donut

8.7
Donut Shop · East Chatham · 8249 S Cottage Grove Ave (at E. 83rd St.), Chicago, IL

Explore ChicagoExplore Chicago: This take-out bakery specializes in the "Big Dat" an enormous doughnut, measuring 9" across and 3" tall.

Dat Old Fashioned Donut is one of The Windy City Badge.

2. Dat Old Fashioned Donut

Donut Shop · Morgan Park · 1979 W 111th St, Chicago, IL

Explore ChicagoExplore Chicago: This take-out bakery specializes in the "Big Dat" an enormous doughnut, measuring 9" across and 3" tall.

The Oriental Institute is one of The Windy City Badge.

3. The Oriental Institute

9.5
History Museum · Hyde Park · 1155 E 58th St (btwn Woodlawn Ave & University Ave), Chicago, IL

Explore ChicagoExplore Chicago: One of Chicago’s Always Free Attractions, the museum has a collection of treasures from the Middle East such as a 5,000 year old mummy, a 40-ton Assyrian sculpture & a 17-foot tall statue of King Tut. Read more.

Chicago Velo Campus is one of The Windy City Badge.

4. Chicago Velo Campus

9.4
Racetrack · South Chicago · 8615 S Burley Ave, Chicago, IL

Explore ChicagoExplore Chicago: The Chicago Velo Campus is a large, banked track for bicycle racing, and is the first velodrome built in Chicago in a generation.

Vida Simple Mural By Juan Angel Chávez is one of The Windy City Badge.

5. Vida Simple Mural By Juan Angel Chávez

8.1
Art Gallery · Heart of Chicago · 2010 S Damen Ave (at CTA - Damen/Cermak), Chicago, IL

Explore ChicagoExplore Chicago: Located just outside the Damen Pink Line ‘L’ Stop,this mural focuses on the individuality of the people that created the heritage and cultural identity of the community. Read more.

Garfield Park Conservatory is one of The Windy City Badge.

6. Garfield Park Conservatory

Garden · East Garfield Park · 300 N Central Park Ave (at Lake St), Chicago, IL

Explore ChicagoExplore Chicago: Often referred to as “landscape art under glass,” the free admission conservatory occupies approximately 4.5 acres inside and out, where thousands of plant species are on display. Read more.

Co-Prosperity Sphere is one of The Windy City Badge.

7. Co-Prosperity Sphere

8.7
Art Gallery · Bridgeport · 3219 S Morgan St (at 32nd St), Chicago, IL

Explore ChicagoExplore Chicago: Stroll past three large window galleries with new and engaging artwork to enjoy. This “experimental cultural center” produces art exhibitions, readings, and performances. Read more.

Ping Tom Memorial Park is one of The Windy City Badge.

8. Ping Tom Memorial Park

9.4
Park · Armour Square · 300 W 19th St (btwn Lumber St & Wentworth Ave), Chicago, IL

Explore ChicagoExplore Chicago: Among the Park’s cool features are a pagoda-shaped pavilion, where you can catch a water taxi to downtown Chicago, and a unique railroad drawbridge. Read more.

Merz Apothecary is one of The Windy City Badge.

9. Merz Apothecary

9.0
Drugstore / Pharmacy · 4716 N Lincoln Ave (at W Leland Ave), Chicago, IL

Explore ChicagoExplore Chicago: Around since 1875, this apothecary's original location is stacked floor-to-ceiling with every medicine, scent and homeopathic brand you can think of. It's one of Lincoln Square's many hip boutiques. Read more.

Andersonville Swedish Dala Horse is one of The Windy City Badge.

10. Andersonville Swedish Dala Horse

8.6
Sculpture Garden · Andersonville · Clark St. & Farragut Ave., Chicago, IL
Jane Addams Hull-House Museum is one of The Windy City Badge.

11. Jane Addams Hull-House Museum

8.5
History Museum · University Village - Little Italy · 800 S Halsted St (at UIC), Chicago, IL

Explore ChicagoExplore Chicago: Today, visitors can explore historic exhibitions, borrow seeds from an heirloom seed library, learn about urban horticulture, eat soup and debate politics, and see contemporary art exhibitions. Read more.

63rd Street Beach is one of The Windy City Badge.

12. 63rd Street Beach

8.7
Beach · 6300 S Lake Shore Dr (at Hayes Dr), Chicago, IL

Explore ChicagoExplore Chicago: This free admission beach is one of Chicago’s 33 sandy Lake Michigan beaches. Read more.

Milios Hair Studio is one of The Windy City Badge.

13. Milios Hair Studio

8.8
Salon / Barbershop · Lakeview · 959 W Belmont Ave (at Sheffield Ave.), Chicago, IL

Explore ChicagoExplore Chicago: Milio’s is the place to go for a punk rock haircut. It’s also the former location of 3 rock clubs that hosted now-famous bands such as the Velvet Underground, Prince, REM, and The Smashing Pumpkins. Read more.

Music Box Theatre is one of The Windy City Badge.

14. Music Box Theatre

9.4
Indie Movie Theater · Lakeview · 3733 N Southport Ave (btwn Grace St & Waveland Ave), Chicago, IL

Explore ChicagoExplore Chicago: The Music Box plays a mix of independent and foreign films, as well as classic (black and white) movie matinees, and midnight screenings of cult classics. Read more.

Glenwood Avenue Arts District is one of The Windy City Badge.

15. Glenwood Avenue Arts District

8.9
General Entertainment · Rogers Park · 6912 N Glenwood Ave (at W Morse Ave), Chicago, IL

Explore ChicagoExplore Chicago: The cobblestone, mural-lined Glenwood Avenue Arts District in Rogers Park is home to award-winning theaters, art galleries, a seasonal farmers market, and cute cafes. Read more.

Michael Jordan Statue is one of The Windy City Badge.

16. Michael Jordan Statue

9.4
Monument / Landmark · Near West Side · United Center (at Wood St), Chicago, IL

Explore ChicagoExplore Chicago: Located outside the United Center’s east end, the sculpture, which can be seen without buying a ticket to a Bulls or Blackhawks game, celebrates one of Chicago’s most internationally known figures. Read more.

Green Mill Cocktail Lounge is one of The Windy City Badge.

17. Green Mill Cocktail Lounge

9.2
Jazz Club · Uptown · 4802 N Broadway St (at W Lawrence Ave.), Chicago, IL

Explore ChicagoExplore Chicago: This Chicago landmark presents jazz nightly, from traditional to experimental, amid a "speakeasyesque" décor. Read more.

DuSable Museum Of African American History is one of The Windy City Badge.

18. DuSable Museum Of African American History

9.2
History Museum · Washington Park · 740 E 56th Pl (S Cottage Grove Ave), Chicago, IL

Explore ChicagoExplore Chicago: Mosaic portraits in Founders Hall celebrate Dr. Margaret Burroughs, co-founder of the museum, Harold Washington, Chicago’s first African American Mayor, and DuSable, Founder of Chicago. Read more.

Revolution Brewing is one of The Windy City Badge.

19. Revolution Brewing

9.4
Brewery · Logan Square · 2323 N Milwaukee Ave (btwn N California & W Fullerton Ave), Chicago, IL

Explore ChicagoExplore Chicago: Located in trendy Logan Square, Revolution Brewing is one of Chicago’s artisanal brewing companies. Try the Bacon Fat Popcorn at their restaurant, which also has vegan-friendly options. Read more.

Chicago's Home Of Chicken & Waffles is one of The Windy City Badge.

20. Chicago's Home Of Chicken & Waffles

8.5
Southern / Soul Food Restaurant · Grand Boulevard · 3947 S King Dr (at E Oakwood Blvd.), Chicago, IL

Explore ChicagoExplore Chicago: Popular with locals and visitors, Chicago’s Home of Chicken & Waffles serves soul food up in a stylish dining room. Read more.

Quimby's is one of The Windy City Badge.

21. Quimby's

9.0
Bookstore · Bucktown · 1854 W North Ave (at N Wolcott Av), Chicago, IL

Explore ChicagoExplore Chicago: Quimby’s features one-of-a-kind publications such as small and independent press books, magazines, zines, and underground comics, like Chicago cartoonist Chris Ware's Quimby the Mouse.