10 Best Chicago Holiday Date Night Ideas

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

  • 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

  • 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.

  • 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

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

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

  • 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. 

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

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

  • 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

This checklist was created by ggc

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