Originally Posted by
chgoeditor
Because so many places have New Year's packages, we'd really need a bit more guidance to make recommendations. Age, interests, price point, etc.?
Agreed. Based on the facts that the OP will be here only for 2 nights and it will probably be -2 F at that time, I'd suggest staying mainly in the downtown area for everything (generally speaking - loop, River North, and West Loop). I rarely recommend that, but who visits Chicago in January
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My suggestion to the OP is to do a little research on hotels, restaurants, etc. and come back here with some questions and we'll be much more useful. Chicago has too many good hotels, restaurants, bars to just ask open-ended questions.
Additional questions:
Hotel - do you prefer a small boutique or a major chain?
Restaurants - type of food and price range?