Chicago dates and fun

1. Balmoral Restaurant

40w099 || Route 64, Campton Hills, IL

Scottish Restaurant · 1 tip

River Roast is one of Chicago dates and fun.

2. River Roast

8.7

315 N La Salle Dr, Chicago, IL

Restaurant · River North · 54 tips and reviews

Timothy O'Toole's Pub Chicago is one of Chicago dates and fun.

3. Timothy O'Toole's Pub Chicago

8.0

622 N Fairbanks Ct (at E Ontario St), Chicago, IL

Sports Bar · Streeterville · 137 tips and reviews

Green Mill Cocktail Lounge is one of Chicago dates and fun.

4. Green Mill Cocktail Lounge

8.9

4802 N Broadway St (at W Lawrence Ave), Chicago, IL

Jazz and Blues Venue · Uptown · 136 tips and reviews

BomboBar is one of Chicago dates and fun.

5. BomboBar

8.0

832 West Randolph Street (Randolph), Chicago, IL

Dessert Shop · Fulton Market · 22 tips and reviews

Wilde Bar & Restaurant is one of Chicago dates and fun.

6. Wilde Bar & Restaurant

8.5

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

Pub · Lake View East · 148 tips and reviews

Beatnik is one of Chicago dates and fun.

7. Beatnik

8.0

1604 W Chicago Ave (Ashland), Chicago, IL

Cocktail Bar · East Ukrainian Village · 26 tips and reviews

iO Chicago is one of Chicago dates and fun.

8. iO Chicago

8.8

1501 N Kingsbury St (Blackhawk), Chicago, IL

Comedy Club · 88 tips and reviews

The Signature Room at the 95th is one of Chicago dates and fun.

9. The Signature Room at the 95th

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

American Restaurant · Streeterville · 157 tips and reviews

Bavette's Bar & Boeuf is one of Chicago dates and fun.

10. Bavette's Bar & Boeuf

9.2

218 W Kinzie St (at N Wells St), Chicago, IL

Steakhouse · River North · 130 tips and reviews

Cindy's is one of Chicago dates and fun.

11. Cindy's

8.8

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

New American Restaurant · The Loop · 148 tips and reviews

Maude's Liquor Bar is one of Chicago dates and fun.

12. Maude's Liquor Bar

840 W Randolph St (btwn Green St & Peoria St), Chicago, IL

French Restaurant · Fulton Market · 104 tips and reviews

Osaka Garden is one of Chicago dates and fun.

13. Osaka Garden

8.8

5800 S Lake Shore Drive, Chicago, IL

Garden · 15 tips and reviews

The Hideout is one of Chicago dates and fun.

14. The Hideout

8.7

1354 W Wabansia Ave (btwn Elston Ave & Throop St), Chicago, IL

Rock Club · Bucktown · 57 tips and reviews

The J. Parker is one of Chicago dates and fun.

15. The J. Parker

7.8

1816 N Clark St, Chicago, IL

Roof Deck · Old Town Triangle · 73 tips and reviews

Ada Street is one of Chicago dates and fun.

16. Ada Street

8.9

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

American Restaurant · Bucktown · 67 tips and reviews

Brimfield is one of Chicago dates and fun.

17. Brimfield

7.5

5219 N Clark St (btwn Foster & Farragut), Chicago, IL

Antique Store · Andersonville · 16 tips and reviews

Gene’s Sausage Shop is one of Chicago dates and fun.

18. Gene’s Sausage Shop

9.3

4750 N Lincoln Ave (btwn Lawrence Ave & Leland Ave), Chicago, IL

Butcher · Ravenswood · 71 tips and reviews

ENJOY, AN URBAN GENERAL STORE is one of Chicago dates and fun.

19. ENJOY, AN URBAN GENERAL STORE

8.3

4723 N Lincoln Ave (btwn Lawrence & Leland), Chicago, IL

Gift Store · Ravenswood · 16 tips and reviews

Lost Lake is one of Chicago dates and fun.

20. Lost Lake

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

Tiki Bar · Logan Square · 53 tips and reviews

McDonald’s Global Menu Restaurant is one of Chicago dates and fun.

21. McDonald’s Global Menu Restaurant

8.3

1035 W Randolph St (at N Carpenter St), Chicago, IL

Fast Food Restaurant · West Town · 10 tips and reviews

Revival Food Hall is one of Chicago dates and fun.

22. Revival Food Hall

8.7

125 S Clark St (W Adams St), Chicago, IL

Food Court · The Loop · 54 tips and reviews

Royal Palms Shuffleboard Club is one of Chicago dates and fun.

23. Royal Palms Shuffleboard Club

8.9

1750 N Milwaukee Ave, Chicago, IL

Tiki Bar · Bucktown · 10 tips and reviews