Chicago, IL

1. Little Goat Diner

820 W Randolph St (at Green St), Chicago, IL

Diner · Fulton Market · 472 tips and reviews

Casi Gerber: Rooftop seating with views of the downtown skyline

2. Fountainhead

1970 W Montrose Ave (at N Damen Ave), Chicago, IL

Bar · Ravenswood · 100 tips and reviews

Casi Gerber: Rooftop seating + a stellar craft beer and whiskey selection.

Homestead on the Roof is one of Chicago, IL.

3. Homestead on the Roof

8.1

1924 W Chicago Ave (at Winchester), Chicago, IL

New American Restaurant · East Ukrainian Village · 26 tips and reviews

Casi Gerber: Rooftop seating + crispy chicken skins and creamy egg duck carbonara.

4. Terzo Piano

8.4

159 E Monroe St (at S Michigan Ave), Chicago, IL

Italian Restaurant · Grant Park · 51 tips and reviews

Casi Gerber: In the Art Institute’s Modern Wing with a one of the best views of the Chicago skyline.

5. The Purple Pig

500 N Michigan Ave (at W Illinois St), Chicago, IL

Mediterranean Restaurant · Streeterville · 633 tips and reviews

6. Grant Park

9.5

337 E Randolph Dr (at Michigan Ave), Chicago, IL

Park · 136 tips and reviews

7. Cloud Gate

9.3

N Michigan Ave (btwn Randolph St & Monroe Dr), Chicago, IL

Outdoor Sculpture · Grant Park · 302 tips and reviews

Millennium Park Chiropractic is one of Chicago, IL.

8. Millennium Park Chiropractic

155 N Michigan Ave (Randolph and Michigan), Chicago, IL

Chiropractor · The Loop · No tips or reviews

9. 360 CHICAGO

8.9

875 N Michigan Ave Fl 94 (btwn Delaware Pl & Chestnut St), Chicago, IL

Scenic Lookout · Streeterville · 167 tips and reviews

10. Skydeck Chicago

8.4

233 S Wacker Dr (btwn Adams St & Jackson Blvd), Chicago, IL

Scenic Lookout · The Loop · 392 tips and reviews

11. Wrigley Field

9.2

1060 W Addison St (btwn Sheffield Ave & Clark St), Chicago, IL

Baseball Stadium · Wrigleyville · 573 tips and reviews

12. Crown Fountain

8.8

Michigan Ave (btwn S Michigan Ave and Boeing Gallery S), Chicago, IL

Fountain · Grant Park · 63 tips and reviews

Chicago Water Tower is one of Chicago, IL.

13. Chicago Water Tower

8.8

806 N Michigan Ave (btwn Pearson St & Chicago Ave), Chicago, IL

Historic and Protected Site · Streeterville · 40 tips and reviews

14. Lake Michigan

Lake Michigan, Chicago, IL

Lake · 81 tips and reviews

Lincoln Park Conservatory is one of Chicago, IL.

15. Lincoln Park Conservatory

9.3

2391 N Stockton Dr (at Fullerton Pkwy), Chicago, IL

Garden · Lincoln Park · 58 tips and reviews

Chicago Botanic Garden is one of Chicago, IL.

16. Chicago Botanic Garden

9.5

1000 Lake Cook Rd (btwn Green Bay Rd & Skokie Hwy), Glencoe, IL

Botanical Garden · 128 tips and reviews

17. Willis Tower

8.6

233 S Wacker Dr (btwn W Adams St & W Jackson Blvd), Chicago, IL

Structure · The Loop · 308 tips and reviews

Goose Island Brewpub is one of Chicago, IL.

18. Goose Island Brewpub

1800 N Clybourn Ave (at Willow St), Chicago, IL

Brewery · North Side · 175 tips and reviews

Revolution Brewing is one of Chicago, IL.

19. Revolution Brewing

9.2

2323 N Milwaukee Ave (btwn N California & W Fullerton Ave), Chicago, IL

Brewery · Logan Square · 391 tips and reviews

Lucky's Sandwich Co. is one of Chicago, IL.

20. Lucky's Sandwich Co.

7.9

3472 N Clark St (btwn W Cornelia Ave & W Newport Ave), Chicago, IL

Sandwich Spot · Lakeview · 69 tips and reviews

21. Guthrie's Tavern

8.9

1300 W Addison St (at Lakewood Ave), Chicago, IL

Bar · Lakeview · 63 tips and reviews

22. Goose Island Brewpub

3535 N Clark St (btwn Addison St & Newport Ave), Chicago, IL

Brewery · Wrigleyville · 99 tips and reviews

Lagunitas Brewing Company is one of Chicago, IL.

23. Lagunitas Brewing Company

2607 W 17th St, Chicago, IL

Brewery · Douglas Park · 87 tips and reviews

Chicago Architecture Center River Cruise is one of Chicago, IL.

24. Chicago Architecture Center River Cruise

9.4

112 E Wacker Dr (at Michigan Ave), Chicago, IL

Tour Provider · The Loop · 105 tips and reviews