Dine, Drink & Do Date Night in Chicago

Updated: Jan 3, 2019

Chicago has great date night spots, and with its expansive dining, drink, and entertainment options, I feel like you could do something every weekend and still not scratch the surface of what it has to offer.


Domenic and I (really try) to make Thursday night date night. (Sometimes it comes in the form of Chinese take-out and sweats, but you can't win 'em all!)


When we've had the time and money to spruce up Thursday evenings, here are some of the spots we've hit.


Where to Eat

Cafe Ba-Ba-Reeba!, Lincoln Park

Tapas, Paella, Sangria


Untitled Supper Club, West Loop

A sultry underground speakeasy


Gosu, Logan Square

Personal opinion: The best sushi within Chicago's city limits!


Scofflaw, Logan Square

The service is great, portions are generous, and the silky, dim aesthetic is perfect for a fall or winter dinner


After Dinner Activity

Concerts/Movies in the Park, Millennium Park

All summer long, the park is a perfect date night



Game Room in Chicago Athletic Association, The Loop

Bocce, foosball, shuffleboard in a old-time club


The iO Theater, Lincoln Park

Intimate improv, immensely funny


The Art Institute of Chicago, The Loop

Get lost in exhibits on Thursdays when admission is free for Chicago residents!


Schuba's + Lincoln Hall, Lake View, Lincoln Park

Check out the upcoming line up at either of these intimate venues


Night Cap Spots

London House, Downtown

Craft cocktails and a view overlooking the river and Tribune Tower


The Berkshire Room, River North

An airy cocktail lounge with open-face booths


Delilah's, Lake View

A dive bar adorned with holiday lights all year round and a documentary playing every time you pop in


Cherry Circle Room in Chicago Athletic Association, The Loop

Step over to Cherry Circle Room after the bocce and foosball


Wilde, Lake View

As an ode to Oscar Wilde, this bar/restaurant has a library nook and gorgeous old wood bar

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