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Zoo Lights, always
christmas carol play, kristkindle market in wrigley, lights at the zoo, a lot of your favorite bars decked out in christmas garb, ice skating, macys windows, navy pier, etc etc
Ditto for the market at Wrigley, it was fun.
Walnut Room at Macys. Ice skating at any outdoor rink in the city.
Check on OpenTable a few hours before visit. Spots usually open up.
The Music Box usually plays old Christmas movies and there is a full theater sing along of old Christmas tunes, was really fun last year
Thorne Rooms at the Art Institute decorated for Christmas!
Ice Cream Museum was wholesome fun
Buttcracker, LGBT Burlesque show was super fun