14 of the Cutest Things to do on Valentine’s Day in Chicago 2019

Enjoy candy\'s and cocktails at Cindy’s Rooftop Candies Pop-up Shop

For the Love of Skating, Couples Skate at The Chicago Athletic Association Hotel

Dine at one of the best restaurants in Chicago at Maple & Ash

Relax in ultimate luxury at Aire Ancient Baths

Make dinner together at home and order a famous Portillo’s Chocolate Cake

Get tickets to the NAKED Scavenger Hunt at The Art Institute

Plan a Chicago Staycation at some of the best hotels in Chicago

Valentine’s Day with The Princess Bride at The Music Box Theatre

See the lights of Chicago with a Helicopter Tour of the City

Enjoy Valentine’s Day Treats at Dylan’s Candy Bar

Listen to romantic jazz music at Winter Jazz Club

Plan a Valentine\'s Day couples date with a Speakeasy Murder Mystery Cocktail Party

Fondue for two at Geja’s Cafe

Grab a box of Valentine\'s donuts at Stan Donuts #donutdate

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