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Given the choice I think NY is more magical, but there is plenty of magic in Chicago around Christmas time as well. (I live in Chicago). High tea at the drake, Michigan Ave all lit up, tree at macys, the hotels are all decked out, the shopping is great, lots of merriment to be had.
NEW YORK HAS FULL OF GARBAGE ON THE STREET
Save Chicago for the summer
NY would be my vote as a current chicago resident
You can’t beat Christmas in New York
The Wind 🌬️ Off Of The Lake/Sea Of Michigan Can Be Brutal In The Winter/Right Around The Holidays ✌🏽
be aware ny is super expensive during christmas, an average hotel can cost you 600-800 a night.