10 Best Chicago Holiday Date Night Ideas

Sometimes experiences with loved-ones are way better than gifts. If you are looking to do something a little different this year or if you are looking to impress that special someone, use this list to create something special and different this holiday season.

The 10 Best Chicago Holiday Date Night Ideas
  • Go see It's A Wonderful Life at The Music Box Theatre followed by dinner at Ella Elli

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  • Grab a hot chocolate from Geja's Hot Chocolate stand and take a romantic walk through Zoo Lights at Lincoln Park Zoo. Make a reservation for two at Mon Ami Gabi

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  • Meet for a coffee or hot chocolate date at Colectivo Coffee in Andersonville and spend the afternoon strolling around the antique stores. Buy a holiday ornament for your tree.

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  • Head to Millennium Park on Friday nights to hear the Carolers or go ice skating. Warm up with a hot toddy and view the holiday lights of the city from the rooftop of Cindy's

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  • Enjoy an over-the-top Christmasy date night at the Santa Baby Pop-up Bar. The decor and drinks are definitely worth it!  

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  • Take the CTA holiday train downtown and enjoy hot spiced wine and even a game or two of curling at Upstairs at The Gwen

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  • See the holiday lights on Michigan Avenue  and get deep dish pizza at Labriola and grab tickets to see a Jazz show at Winter Jazz Club right around the corner. 

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  • Hop aboard the Odyssey Riverfront Dinner Cruise and see the lights of the city as you sail along the Chicago River

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  • Relax in luxury in six different semi-private bath pools at  AIRE Ancient Bath followed by dinner in the West Loop

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  • Make reservations at a romantic restaurant like RPM Steak, see a holiday show, A The Christmas Carol is a good one, and end the night with holiday cocktails at SideDoor or The Berkshire Room

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This checklist was created by ggc

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