From tried-and-true classics like ice skating to out-of-the-box dates like indoor rock climbing and renting a hot tub on the Chicago River, this guide has over 20 Chicago winter date ideas.

Play Like Kids Again

Looking for an indoor date idea? Head to the Museum of Ice Cream Chicago, where you can be silly...and enjoy a bunch of free ice cream and other treats. 

Cocktails at Starbucks?!

Rooftop Scene

Chicago's HOT

Think Out of the Box

To really make a first impression, rent a hot tub boat and cruise down the Chicago River (totally serious!)!

Head Indoors

See another side of Chicago's museums

Most of Chicago's world renowned museums host special after-hours events, perfect for date night. Plus, many are FREE for IL residents. 

Learn a New Skill Together

Check out Other Chicago Date Ideas

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