Chicago

1. Butch McGuire's

6.5

20 W Division St (at Dearborn St), Chicago, IL

Pub · Gold Coast · 57 tips and reviews

2. Sparrow

9.2

12 W Elm St (btwn State St & Dearborn St), Chicago, IL

Cocktail Bar · Near North Side · 20 tips and reviews

3. The Flat Iron

1565 N Milwaukee Ave (btwn North Ave & Honore St), Chicago, IL

Bar · Wicker Park · 47 tips and reviews

4. The Owl

6.9

2521 N Milwaukee Ave, Chicago, IL

Bar · Logan Square · 68 tips and reviews

Headquarters Beercade is one of Chicago.

5. Headquarters Beercade

2833 N Sheffield Ave (at Wolfram St), Chicago, IL

Bar · Lakeview · 84 tips and reviews

6. Lost Lake

3154 W Diversey Ave (at Kedzie Blvd), Chicago, IL

Tiki Bar · Logan Square · 53 tips and reviews

7. East Room

6.6

2828 W Medill Ave (W Medill Ave), Chicago, IL

Cocktail Bar · Logan Square · 18 tips and reviews

8. Remedy

8.3

1910 N Milwaukee Ave (Armitage/Western), Chicago, IL

Cocktail Bar · Bucktown · 6 tips and reviews

9. The Violet Hour

8.9

1520 N Damen Ave (at Pierce Ave), Chicago, IL

Speakeasy · Wicker Park · 255 tips and reviews

10. Fountainhead

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

Bar · Ravenswood · 100 tips and reviews

11. The Monkey's Paw

8.6

2524 N Southport Ave, Chicago, IL

Whisky Bar · North Side · 26 tips and reviews

12. RM Champagne Salon

116 N Green St (btwn Randolph St & Washington Blvd), Chicago, IL

Bistro · West Town · 68 tips and reviews

13. Ten Cat Tavern

7.4

3931 N Ashland Ave (at Irving Park Rd.), Chicago, IL

Dive Bar · Lakeview · 18 tips and reviews

14. The Dawson

8.6

732 W Grand Ave (at N Halsted St), Chicago, IL

New American Restaurant · Fulton River District · 96 tips and reviews

Fireside Restaurant & Lounge is one of Chicago.

15. Fireside Restaurant & Lounge

8.1

5739 N Ravenswood Ave (at W Rosehill Dr), Chicago, IL

Bar · Edgewater · 53 tips and reviews

16. Old Town Social

455 W North Ave (at N Cleveland Ave), Chicago, IL

Gastropub · Old Town · 121 tips and reviews

17. Hubbard Inn

6.9

110 W Hubbard St (btwn Clark St. & LaSalle Blvd.), Chicago, IL

American Restaurant · River North · 94 tips and reviews

Wilde Bar & Restaurant is one of Chicago.

18. Wilde Bar & Restaurant

8.5

3130 N Broadway St (at W Briar Pl), Chicago, IL

Pub · Lake View East · 147 tips and reviews

19. Cindy's

8.6

12 S Michigan Ave (btwn E Madison & E Monroe St), Chicago, IL

New American Restaurant · The Loop · 144 tips and reviews

20. The Drawing Room

8.8

12 S Michigan Ave (Madison), Chicago, IL

Lounge · The Loop · 14 tips and reviews

21. Game Room

8.9

12 S Michigan Ave (at E Madison St.), Chicago, IL

Bar · The Loop · 33 tips and reviews

22. Sable Kitchen & Bar

505 N State St (at W Illinois St), Chicago, IL

New American Restaurant · Near North Side · 198 tips and reviews

Broken Shaker at Freehand Chicago is one of Chicago.

23. Broken Shaker at Freehand Chicago

8.6

19 E Ohio St (State), Chicago, IL

Cocktail Bar · Near North Side · 65 tips and reviews

24. Drumbar

7.9

201 E Delaware Pl (at Mies van der Rohe Way), Chicago, IL

Cocktail Bar · Streeterville · 68 tips and reviews

25. DOC Wine Bar

2602 N Clark St, Chicago, IL

Wine Bar · Park West · 33 tips and reviews

26. Rootstock

9.2

954 N California Ave (at Augusta Blvd), Chicago, IL

New American Restaurant · Humboldt Park · 58 tips and reviews

27. Penelope's

8.2

1913 W Division St (btwn N Winchester Ave & N Wolcott), Chicago, IL

Boutique · Wicker Park · 7 tips and reviews

28. Tortoise Supper Club

8.3

350 N State St, Chicago, IL

American Restaurant · Near North Side · 51 tips and reviews

Sheffield's Beer & Wine Garden is one of Chicago.

29. Sheffield's Beer & Wine Garden

8.9

3258 N Sheffield Ave (at W School St), Chicago, IL

Beer Garden · Lakeview · 108 tips and reviews

30. The Hangge-Uppe

5.7

14 W Elm St (btwn N State St. & N Dearborn St.), Chicago, IL

Dive Bar · Near North Side · 44 tips and reviews

31. The Kerryman

6.8

661 N Clark St (at W Erie St), Chicago, IL

Pub · Near North Side · 65 tips and reviews

32. The Patisserie

11 E Walton St (Rush St), Chicago, IL

Café · Gold Coast · 1 tip

33. Bad Hunter

802 W Randolph St (btwn Halsted St & Green St), Chicago, IL

New American Restaurant · Fulton Market · 32 tips and reviews

34. The Press Room

8.8

1134 W Washington Blvd, Chicago, IL

Wine Bar · West Town · 1 tip

Table, Donkey and Stick is one of Chicago.

35. Table, Donkey and Stick

8.8

2728 W Armitage Ave (btwn N California Ave & N Point St), Chicago, IL

New American Restaurant · Logan Square · 36 tips and reviews

36. Maison Marcel

8.2

3114 N Broadway St (W Barry Ave), Chicago, IL

Bakery · Lake View East · 14 tips and reviews

37. Beatrix

8.9

519 N Clark St (at W Grand Ave), Chicago, IL

New American Restaurant · River North · 233 tips and reviews

Stan's Donuts & Coffee is one of Chicago.

38. Stan's Donuts & Coffee

8.5

1560 N Damen Ave (at N Milwaukee Ave), Chicago, IL

Donut Shop · Wicker Park · 131 tips and reviews

39. Stan's Donuts & Coffee

8.9

3300 N Broadway St (at W Aldine Ave), Chicago, IL

Donut Shop · Lake View East · 17 tips and reviews

40. 3 Arts Club Cafe

9.1

1300 N Dearborn St (at W Goethe St), Chicago, IL

Café · Gold Coast · 83 tips and reviews

41. etta

8.4

1840 W North Ave, Chicago, IL

New American Restaurant · Bucktown · 15 tips and reviews

42. Cafe Cancale

1576 N Milwaukee Ave, Chicago, IL

French Restaurant · Wicker Park · 5 tips and reviews

Joe’s Imports Wine Bar is one of Chicago.

43. Joe’s Imports Wine Bar

813 W Fulton Market, Chicago, IL

Wine Bar · Fulton Market · 4 tips and reviews

44. Somerset

8.2

1112 N. State Street (btwn Elm St & Maple St), Chicago, IL

Restaurant · Near North Side · 19 tips and reviews

45. Serena And Lily

853 W Armitage Ave, Chicago, IL

Furniture and Home Store · North Side · No tips or reviews

46. Devereaux

8.5

1112 N State St Fl 18 (Chestnut St), Chicago, IL

Hotel Bar · Near North Side · No tips or reviews

47. The J. Parker

7.6

1816 N Clark St., 13 Th Floor, Chicago, IL

Roof Deck · Old Town Triangle · 72 tips and reviews

48. Cafe Spiaggia

980 N Michigan Ave, Chicago, IL

Italian Restaurant · Streeterville · 22 tips and reviews

The Signature Lounge at the 96th is one of Chicago.

49. The Signature Lounge at the 96th

7.4

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

Lounge · Streeterville · 307 tips and reviews

50. Aba

9.4

302 N Green St (Fulton St), Chicago, IL

Mediterranean Restaurant · Fulton Market · 21 tips and reviews

51. Daisies

9.1

2375 N Milwaukee Ave, Chicago, IL 60647 (Fullerton Ave), Chicago, IL

New American Restaurant · Logan Square · 12 tips and reviews

Southport Grocery & Cafe is one of Chicago.

52. Southport Grocery & Cafe

9.1

3552 N Southport Ave (at W Addison St), Chicago, IL

Breakfast Spot · Lakeview · 90 tips and reviews

Raised Rooftop at Renaissance Hotel is one of Chicago.

53. Raised Rooftop at Renaissance Hotel

8.2

1 W Wacker Dr, Chicago, IL

Roof Deck · The Loop · 22 tips and reviews

Tony Dmartino: Rooftop bar. Great view of Chicago River and Loop buildings. Third level rooftop with glass walls so you am still see all the hustle and bustle of Chicago beneath you

54. The Terrace at Trump

7.8

Trump International Hotel & Tower Chicago, Chicago, IL

Restaurant · Near North Side · 52 tips and reviews

Pritzker Military Museum and Library is one of Chicago.

55. Pritzker Military Museum and Library

6.4

104 S Michigan Ave (at W Monroe), Chicago, IL

Library · The Loop · 11 tips and reviews

Time Out Chicago: This small but comprehensive military library is known for its excellent lecture series. An exhibit space shows off guest artists; exhibitions rotate with a focus on war imagery.

56. Untitled Supper Club

8.5

111 W Kinzie St (btwn N LaSalle St & N Clark St), Chicago, IL

Restaurant · River North · 141 tips and reviews

Kyle Stoner: GREAT cocktails, but bizarre dress code discourages current/up-to-date fashion. Guys should dress business casual to avoid doorman scrutiny.