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Swizzle #7 at Scofflaw
Photograph: Courtesy Scofflaw

Real Chicagoans share their go-to date night spots

We asked Chicago Tastemakers to spill their trusted date destinations

Written by
Time Out Tastemakers
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Whether it's your first date or your 50th, choosing the perfect destination is never an easy charge. Are you looking for something laid-back and familiar or new and exciting? Hoping to save money or looking to ball out? In a city as vast as Chicago, there are thousands of date ideas at our fingertips: On any given night, you could scope out a new restaurant, score tickets to a Broadway show, sip cocktails on a rooftop or check out one of the city's many free attractions. We tapped our Tastemaker community with a simple question: What's your go-to Chicago date night spot? They shared no-fail options that have stood the test of time (and romance!).

RECOMMENDED: Let Time Out Chicago set you up on a blind date

Chicagoans’ favorite date destinations

  • Bars
  • Cocktail bars
  • River North
  • price 2 of 4

"You almost feel like you're drinking tropical drinks in a woodsy 1970s den. I'd definitely recommend it as a little escape in the winter time or as a fun place to grab a great tiki drink come summer." —Mary McMahon

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Volo Restaurant Wine Bar
  • Restaurants
  • Contemporary American
  • North Center
  • price 1 of 4

"Volo is a great oasis in the big city. They have great shared dishes and lovely wine options. The beer garden is small and quiet and very intimate. It's a great place to take a date." —Heather Payne

  • Bars
  • Wine bars
  • Lincoln Park
  • price 1 of 4

"I love D.O.C. Wine Bar in Lakeview for the first couple of dates. The servers here are wine experts, and the dimly lit setting is the perfect place to get to know someone over a bottle." —Mary McMahon

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Maude’s Liquor Bar
  • Restaurants
  • French
  • West Loop
  • price 3 of 4

"Maude's Liquor Bar in the West Loop has the same intimate feel as Bavette's but with half the wait. Buy yourself and your date $8 whiskey shots as an ice breaker. Once your eyes adjust to the darkness, feast on fancy French fare by candlelight." —Nicole Long

  • Restaurants
  • American
  • Lincoln Square
  • price 2 of 4

"They have the best Philly cheesesteak in the city—hands down. They fly in their bread fresh daily from Phildadelphia and have a really thoughtful local draft list. If you want your date night to get really crazy, they have $1 fireball shots." —Hilary Mikulich

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  • Restaurants
  • Mexican
  • River North
  • price 2 of 4

"Mercadito is a great date spot, serving contemporary Mexican-inspired eats and cocktails in a chic and upbeat environment. The downstairs speakeasy, Double A, is also an intimate, cozy venue [where you can] continue the evening with throwback hip-hop music and craft cocktails." —Kanchan Garg

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  • Bars
  • Lounges
  • Logan Square
  • price 2 of 4

"Scofflaw is romantic with its marble bar, fireplace and shabby-chic charm. It's also delicious and reasonably priced. I come here often for drinks and a burger with [my] husband after a show at the Logan Theatre—which you can also, ahem, drink at." —Jill Failla

  • Music
  • Music venues
  • Streeterville

"Winter’s Jazz Club is the perfect intimate spot for a romantic date. It's classic Chicago with its top-notch musical lineup and spectacular location on the river. It also boasts a well-curated wine list and candlelight to set the mood." —Kristy Katzmann

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  • Restaurants
  • Chinese
  • Lincoln Park
  • price 2 of 4

"Dee's is a sleek Chinese piano bar on Armitage; it's my personal favorite when there's a special occasion or something worth celebrating. It's cozy and has live jazz on weekends, which creates a perfect ambience for enjoying their extensive menu, including an unforgettable mushu dish that they prepare at your table." —Carolyn Moore

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