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The best things in life are free. And by that, we mean free wine tastings and gallery visits, which top our list of eight totally cheap and totally cute dates in Chicago.


CHI date night LIST1

Second Friday in Pilsen

On the second Friday of the month, Pilsen’s galleries open their doors to the public. Bonus: As you stroll from place to place, you can snag free cups of wine and cans of beer.

CHI date night LIST2

Wine Tasting at Lush Wine and Spirits

Keep the Sunday scaries at bay with Lush’s free Sunday wine tastings from 2 to 5 p.m. If things go well, you can always split a $10 bottle and share a charcuterie and cheese board.

CHI date night LIST3

Cupcake Pancakes at Southport Grocery

Step one: Order a plate of cupcake pancakes (made from actual cupcake batter) to share. Step two: Judge your date by whether or not they give you the last bite.

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Free Admission at Art Institute of Chicago

Every Thursday night, the museum is free for Illinois residents and open until 8 p.m. All you have to do is show up, wander around and gaze at the art (or into each other’s eyes).

CHI date night LIST4

Whiskey Tasting at Koval

Tours of Chicago’s first craft distillery include numerous samples for just $10. We’ll never settle for dinner and a movie again.

CHI date night LIST6

Prix Fixe Lunch at Blackbird

Warm shrimp salad, duck confit and apple butter ice cream all for $25? We’re in love.

CHI date night list7
The Drake Hotel

Happy Hour at Coq D’Or

This wood-paneled Prohibition-era lounge at The Drake will make you feel like a million bucks—even while you’re taking advantage of happy hour prices (Monday through Thursday, 5 to 7 p.m.).

CHI date night LISt8

Movie Night at the Music Box

Make Monday the new movie night with Music Box’s reduced admission ($7 compared with the usual $10). Best of all, there’s BOGO popcorn and soda.

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