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Wine and dine

1. Havana Grill & Mojito Bar

8.0
412 N Clark St (between W Hubbard St & W Kinzie St), Chicago, IL
Cuban Restaurant · River North · 62 tips and reviews

Crain's Chicago BusinessCrain's Chicago Business: The ceviche mixto is especially enticing for summer meals, with its citrusy mix of marinated blue marlin, sea scallops and calamari, topped with avocado and lime. Read more.

2. Holiday Grill & Bar

740 W Randolph St (at N Halsted St), Chicago, IL
Bar · Fulton Market · 18 tips and reviews

Tim S.Tim Scoutelas: No draft beer but a local, more low key hangout as opposed to The Haymarket across the street.

3. Jimmy Green's

825 S State St (btwn E 8th St & E 9th St), Chicago, IL
Sports Bar · Dearborn Park · 56 tips and reviews

AskMenAskMen: Boasting 22 screens & more than 50 beers, providing patrons with an upscale sports lounge spot that’s perfect for catching the game & checking out the local crowd. Full menu available on June 4. Read more.

4. ROOF on theWit

7.5
201 N State St (at Lake St), Chicago, IL
Hotel Bar · The Loop · 131 tips and reviews

Time Out ChicagoTime Out Chicago: TheWit Hotel’s swank rooftop lounge sports a specialty cocktail menu, a well-curated wine list and Mediterranean small plates. Read more.

Elephant & Castle is one of Wine and dine.

5. Elephant & Castle

7.3
111W W Adams St (Clark), Chicago, IL
Pub · The Loop · 68 tips and reviews

6. The Beer Bistro

1061 W Madison St (at Aberdeen St), Chicago, IL
Bar · Near West Side · 90 tips and reviews

Julie P.Julie Popper: $5 pizza Mondays - nom nom nom.

Beef and Brandy is one of Wine and dine.

7. Beef and Brandy

127 S State St (Adams), Chicago, IL
American Restaurant · The Loop · 39 tips and reviews

8. Public House

400 North State Street (at Kinzie St), Chicago, IL
Bar · Near North Side · 167 tips and reviews

ThrillistThrillist: Go to this "Pour-it-yourself" pub if you're into stuff like in-table liquor taps to the mix (plus an eight-tap, serve-yourself "walltender". Yes, you're into that. Read more.

9. Japonais by Morimoto

600 W Chicago Ave (at Larrabee St), Chicago, IL
Japanese Restaurant · 90 tips and reviews

ShopTRACY B.ShopTRACY BURTON: amazing service.....never had a bad experience! thx

Sweetwater Tavern & Grille is one of Wine and dine.

10. Sweetwater Tavern & Grille

8.3
225 N Michigan Ave (at S Water St), Chicago, IL
American Restaurant · The Loop · 198 tips and reviews

L P.L P: Sweetwater chopped salad is the best chopped salad my boyfriend and I have ever had!!! So flavorful!

11. The Purple Pig

500 N Michigan Ave (at W Illinois St), Chicago, IL
Mediterranean Restaurant · Streeterville · 633 tips and reviews

ThrillistThrillist: Visit this new haven for "cheese, swine & wine," delivering said goods in a wine bar-meets-butcher shop space with marble countertops and wine barrels jutting out from the wall. Read more.

12. Grand Lux Cafe

600 N Michigan Ave (at Ontario St), Chicago, IL
American Restaurant · Streeterville · 347 tips and reviews

Liz B.Liz B: they have large portions so you might want to share

Rockit Bar and Grill is one of Wine and dine.

13. Rockit Bar and Grill

22 W Hubbard St (btwn N Dearborn St & N State St), Chicago, IL
Bar · Near North Side · 212 tips and reviews
Paris Club Bistro & Bar is one of Wine and dine.

14. Paris Club Bistro & Bar

59 West Hubbard Street (btwn N Clark & N Dearborn St.), Chicago, IL
French Restaurant · Near North Side · 114 tips and reviews

15. N9NE Steakhouse

440 W Randolph St (at N Canal), Chicago, IL
Steakhouse · West Loop · 41 tips and reviews

Crain's Chicago BusinessCrain's Chicago Business: When a steak or seafood entree is too much, miniature sandwiches duplicate "surf and turf": grilled beef tenderloin on one bun, lobster with Dijon aioli on another. Read more.

16. Keefer's Restaurant

20 W Kinzie St (btwn Dearborn St & State St), Chicago, IL
American Restaurant · Near North Side · 42 tips and reviews

Andy P.Andy Phelan: Best local steaks in Chicago!

Carmichael's Chicago Steak House is one of Wine and dine.

17. Carmichael's Chicago Steak House

1052 W Monroe St (at S Aberdeen St), Chicago, IL
Steakhouse · Near West Side · 22 tips and reviews

18. Big Star

9.0
1531 N Damen Ave (at N Wicker Park Ave), Chicago, IL
Taco Restaurant · Wicker Park · 572 tips and reviews

Chet F.Chet Farley: If you think, "Whow $1 Schlitz!? What a good deal!" Make sure you SPECIFY you want the 7oz. You can have 21oz for $3, or 12oz for $3. Your choice, brah.

19. Big Star

9.0
1531 N Damen Ave (at N Wicker Park Ave), Chicago, IL
Taco Restaurant · Wicker Park · 572 tips and reviews

Time Out ChicagoTime Out Chicago: Try this: The pork belly tacos get the attention, but we love the queso fundido.

20. Sunda

8.9
110 W Illinois St (btwn N LaSalle Dr & N Clark St), Chicago, IL
Sushi Restaurant · River North · 288 tips and reviews

ThrillistThrillist: The Lei (Courvoisier VS, cream, apricot juice, simple syrup), which you'll hilariously ask the waitress for in a way that implies you're actually asking her to have sex!! Read more.

The Violet Hour is one of Wine and dine.

21. The Violet Hour

9.1
1520 N Damen Ave (at Pierce Ave), Chicago, IL
Speakeasy · Wicker Park · 256 tips and reviews

BravoBravo: Hidden gem where you must be in the know to get in. Great cocktails with cool infusions. -Mike Isabella, Top Chef

The Underground is one of Wine and dine.

22. The Underground

6.6
56 W Illinois St (at N Dearborn St.), Chicago, IL
Night Club · Near North Side · 61 tips and reviews

Travis A.Travis Allison: Email me for table and/or guest list reservation! Travis at travis@theundergroundchicago.com!

Vivo Restaurant is one of Wine and dine.

23. Vivo Restaurant

838 W Randolph St (at N Green St), Chicago, IL
Italian Restaurant · Fulton Market · 29 tips and reviews

Crain's Chicago BusinessCrain's Chicago Business: The grilled calamari served over greens with zesty lemon vinaigrette and spicy-sweet marinara is one of the finer calamari dishes in town. Read more.

24. Quartino

8.7
626 N State St (at W Ontario St), Chicago, IL
Italian Restaurant · Near North Side · 345 tips and reviews

Crain's Chicago BusinessCrain's Chicago Business: Get the the thin-crust pizza, which manage to be both light and rich. Crusts are crisp, with a bready flavor, and house-made sauce is a knockout. Read more.

25. Café Ba-Ba-Reeba!

9.1
2024 N Halsted St (btwn W Dickens Ave & W Armitage Ave), Chicago, IL
Tapas Restaurant · North Side · 221 tips and reviews

ZAGATZAGAT: Enjoy $3 tapas at the bar from 4–6 PM daily, as well as 10-midnight on Fridays and Saturdays.

26. Haymarket Pub & Brewery

8.2
737 W Randolph St (at Halsted St), Chicago, IL
Brewery · Fulton Market · 174 tips and reviews

Time Out ChicagoTime Out Chicago: Thought you'd want to know: Haymarket Pub & Brewery has been nominated for Best New Bar in Time Out Chicago’s 2011 Eat Out Awards. Vote now! Read more.

27. The Boiler Room

2210 N California Ave (btwn Lyndale St & Palmer St), Chicago, IL
Pizzeria · Logan Square · 153 tips and reviews

Time Out ChicagoTime Out Chicago: Thought you'd want to know: The Boiler Room has been nominated for Best New Bar in Time Out Chicago’s 2011 Eat Out Awards. Vote now! Read more.

28. Molly's Cupcakes

8.9
2536 N Clark St (btwn Wrightwood & Deming), Chicago, IL
Cupcake Shop · Park West · 207 tips and reviews

MazdaMazda: You can be a kid again here. Chomp a red velvet cupcake while swinging on Molly's swing set.

29. Weber Grill Restaurant

8.1
539 N State St (at Grand Ave), Chicago, IL
American Restaurant · Near North Side · 184 tips and reviews

K P.K Pound: Reservations thru opentable.com will cut down on your wait time tremendously .. & opentable is free to use!

30. Revolution Brewing

9.2
2323 N Milwaukee Ave (btwn N California & W Fullerton Ave), Chicago, IL
Brewery · Logan Square · 391 tips and reviews

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.

SUSHISAMBA Chicago is one of Wine and dine.

31. SUSHISAMBA Chicago

504 N Wells St (at W Illinois St), Chicago, IL
Sushi Restaurant · River North · 107 tips and reviews