Places for me and Leo to check out

1. Alain's Restaurant

1355 S Michigan Ave, Chicago, IL

American Restaurant · South Loop · 6 tips and reviews

City Tavern is one of Places for me and Leo to check out.

2. City Tavern

1416 S Michigan Ave (at 14th St), Chicago, IL

American Restaurant · South Loop · 20 tips and reviews

Square One is one of Places for me and Leo to check out.

3. Square One

1400 S Michigan Ave, Chicago, IL

Bar · South Loop · 24 tips and reviews

III Forks Prime Steakhouse is one of Places for me and Leo to check out.

4. III Forks Prime Steakhouse

180 N Field Blvd (400 block E Randolph), Chicago, IL

Steakhouse · Near East Side · 37 tips and reviews

The Matchbox is one of Places for me and Leo to check out.

5. The Matchbox

8.6

770 N Milwaukee Ave, Chicago, IL

Bar · River West · 73 tips and reviews

Cobra Lounge is one of Places for me and Leo to check out.

6. Cobra Lounge

7.5

235 N Ashland Ave (at Fulton St), Chicago, IL

Lounge · Fulton Market · 56 tips and reviews

Viaggio is one of Places for me and Leo to check out.

7. Viaggio

8.4

1330 W Madison St (btwn Loomis St & Ada St), Chicago, IL

Italian Restaurant · Near West Side · 27 tips and reviews

Farmhouse Chicago is one of Places for me and Leo to check out.

8. Farmhouse Chicago

228 W Chicago Ave (btwn Wells St & Franklin St), Chicago, IL

American Restaurant · Near North Side · 139 tips and reviews

La Sirena Clandestina is one of Places for me and Leo to check out.

9. La Sirena Clandestina

954 W Fulton Market, Chicago, IL

Latin American Restaurant · Fulton Market · 67 tips and reviews

Bistro Voltaire is one of Places for me and Leo to check out.

10. Bistro Voltaire

226 W Chicago Ave (at N Franklin St), Chicago, IL

French Restaurant · Near North Side · 17 tips and reviews

Cru Kitchen & Bar is one of Places for me and Leo to check out.

11. Cru Kitchen & Bar

25 E Delaware Pl, Chicago, IL

Wine Bar · Near North Side · 11 tips and reviews

Ada Street is one of Places for me and Leo to check out.

12. Ada Street

9.0

1664 N Ada St (btwn Concord & Wabansia), Chicago, IL

American Restaurant · Bucktown · 67 tips and reviews

Embeya is one of Places for me and Leo to check out.

13. Embeya

564 W Randolph St (at Jefferson St.), Chicago, IL

Asian Restaurant · West Loop · 38 tips and reviews

North Pond is one of Places for me and Leo to check out.

14. North Pond

8.6

2610 N Cannon Dr, Chicago, IL

New American Restaurant · Lincoln Park · 41 tips and reviews

Lula Café is one of Places for me and Leo to check out.

15. Lula Café

9.3

2537 N Kedzie Blvd (btwn Linden & Logan Sq.), Chicago, IL

Café · Logan Square · 256 tips and reviews

Prosecco is one of Places for me and Leo to check out.

16. Prosecco

8.6

710 N Wells St (at W Superior St), Chicago, IL

Italian Restaurant · River North · 30 tips and reviews

1320 N. State Parkway is one of Places for me and Leo to check out.

17. 1320 N. State Parkway

1320 N State Pkwy (Goethe), Chicago, IL

Structure · Gold Coast · No tips or reviews

Taxim is one of Places for me and Leo to check out.

18. Taxim

8.5

1558 N Milwaukee Ave (btwn Damen Ave & North Ave), Chicago, IL

Greek Restaurant · Wicker Park · 51 tips and reviews

Telegraph Wine Bar is one of Places for me and Leo to check out.

19. Telegraph Wine Bar

2601 N Milwaukee Ave, Chicago, IL

Wine Bar · Logan Square · 35 tips and reviews

The Barrelhouse Flat is one of Places for me and Leo to check out.

20. The Barrelhouse Flat

2624 N Lincoln Ave (at W Wrightwood Ave), Chicago, IL

Cocktail Bar · Lincoln Park · 90 tips and reviews

Old Town Social is one of Places for me and Leo to check out.

21. Old Town Social

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

Gastropub · Old Town · 121 tips and reviews

Vera is one of Places for me and Leo to check out.

22. Vera

1023 W Lake St, Chicago, IL

Spanish Restaurant · Fulton Market · 41 tips and reviews

Nightwood Restaurant is one of Places for me and Leo to check out.

23. Nightwood Restaurant

2119 S Halsted St (at 21st Pl), Chicago, IL

New American Restaurant · East Pilsen · 92 tips and reviews

Au Cheval is one of Places for me and Leo to check out.

24. Au Cheval

9.1

800 W Randolph St (at S Halsted St), Chicago, IL

Burger Joint · Fulton Market · 482 tips and reviews

The Grid is one of Places for me and Leo to check out.

25. The Grid

351 W Hubbard St (at N Kingsbury St), Chicago, IL

Sports Bar · River North · 15 tips and reviews

The Ogden is one of Places for me and Leo to check out.

26. The Ogden

6.8

1659 W Ogden Ave (btwn Monroe & Adams), Chicago, IL

Sports Bar · Near West Side · 54 tips and reviews

Yuzu Sushi and Robata Grill is one of Places for me and Leo to check out.

27. Yuzu Sushi and Robata Grill

8.7

1751 W Chicago Ave, Chicago, IL

Japanese Restaurant · East Ukrainian Village · 74 tips and reviews

Bub City is one of Places for me and Leo to check out.

28. Bub City

7.4

435 N Clark St (btwn Illinois & Hubbard St), Chicago, IL

BBQ Joint · Near North Side · 137 tips and reviews

Homestead on the Roof is one of Places for me and Leo to check out.

29. Homestead on the Roof

8.0

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

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

Leopold is one of Places for me and Leo to check out.

30. Leopold

1450 W Chicago Ave (btwn Noble & Ashland), Chicago, IL

Gastropub · Noble Square · 18 tips and reviews

Four Winds Casino is one of Places for me and Leo to check out.

31. Four Winds Casino

8.0

11111 Wilson Rd (at Maudlin Rd.), New Buffalo, MI

Casino · 68 tips and reviews

The Aviary is one of Places for me and Leo to check out.

32. The Aviary

8.8

955 W Fulton Market (at Morgan St.), Chicago, IL

Cocktail Bar · Fulton Market · 174 tips and reviews

Bob San Restaurant is one of Places for me and Leo to check out.

33. Bob San Restaurant

1805-09 W Division St (at Wood St), Chicago, IL

Sushi Restaurant · East Ukrainian Village · 17 tips and reviews

Benjyehuda is one of Places for me and Leo to check out.

34. Benjyehuda

212 W Van Buren St (btwn Franklin & Wells), Chicago, IL

Falafel Restaurant · The Loop · 33 tips and reviews

Serious Eats: Fries with Merkt's Cheddar: Larger fries are crispy on the outside, soft on the inside, and the smaller ones have a crunchiness like potato chips. Try Merkt's Cheddar on the side - fried potato heaven Read more.

La Vaca Margarita Bar is one of Places for me and Leo to check out.

35. La Vaca Margarita Bar

7.3

1160 W 18th St (Racine), Chicago, IL

Mexican Restaurant · Pilsen · 37 tips and reviews

Ruxbin Kitchen is one of Places for me and Leo to check out.

36. Ruxbin Kitchen

851 N Ashland Ave (at Pearson St), Chicago, IL

American Restaurant · Noble Square · 53 tips and reviews

Rootstock is one of Places for me and Leo to check out.

37. Rootstock

9.2

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

New American Restaurant · Humboldt Park · 58 tips and reviews

East Room is one of Places for me and Leo to check out.

38. East Room

6.6

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

Cocktail Bar · Logan Square · 18 tips and reviews

Celeste is one of Places for me and Leo to check out.

39. Celeste

8.0

111 W Hubbard St (btwn Clark & La Salle), Chicago, IL

Cocktail Bar · River North · 39 tips and reviews

Green Street Smoked Meats is one of Places for me and Leo to check out.

40. Green Street Smoked Meats

9.3

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

BBQ Joint · West Town · 151 tips and reviews

Kinmont is one of Places for me and Leo to check out.

41. Kinmont

419 W Superior St, Chicago, IL

Seafood Restaurant · River North · 40 tips and reviews

Cicchetti is one of Places for me and Leo to check out.

42. Cicchetti

671 N St Clair St (at E Erie St), Chicago, IL

Italian Restaurant · Street · 14 tips and reviews

Naansense is one of Places for me and Leo to check out.

43. Naansense

7.3

171 N Wells St (at W Lake St), Chicago, IL

Indian Restaurant · The Loop · 26 tips and reviews

Pearl Tavern is one of Places for me and Leo to check out.

44. Pearl Tavern

180 N Wacker Dr (Randolph), Chicago, IL

Seafood Restaurant · The Loop · 12 tips and reviews

Sticky Rice Chiang Mai is one of Places for me and Leo to check out.

45. Sticky Rice Chiang Mai

1746 N Western Ave (at W St. Paul Ave), Chicago, IL

Thai Restaurant · Logan Square · 9 tips and reviews

The Drum and Monkey is one of Places for me and Leo to check out.

46. The Drum and Monkey

7.1

1435 W Taylor St, Chicago, IL

Pub · University Village - Little Italy · 23 tips and reviews

Beviamo Wine Bar is one of Places for me and Leo to check out.

47. Beviamo Wine Bar

1358 W Taylor St (at S Loomis St), Chicago, IL

Wine Bar · University Village - Little Italy · 17 tips and reviews

Caliterra Bar & Grille is one of Places for me and Leo to check out.

48. Caliterra Bar & Grille

633 N Saint Clair St (at E Ontario St), Chicago, IL

American Restaurant · Streeterville · 3 tips and reviews

Scofflaw is one of Places for me and Leo to check out.

49. Scofflaw

9.3

3201 W Armitage Ave (at Kedzie Ave), Chicago, IL

Cocktail Bar · Logan Square · 149 tips and reviews

Uncommon Ground is one of Places for me and Leo to check out.

50. Uncommon Ground

7.4

3800 N Clark St, Chicago, IL

New American Restaurant · Lakeview · 128 tips and reviews