God I love my hometown. Even though it'll be freezing you'll love the food and beautiful architecture. The neighborhoods are so diverse. I would maybe save that though for warmer weather but stay more in the city. I can't even go back because I hate returning to NOVA it's been many years since I've been back but I really enjoy Old Town and Lincoln Park where I lived. Streeterville isn't a bad place to base yourself as it's close enough to get to the N Neughborhoods but also downtown.

Chicago has amazing restaurants and fun bars. I would definitely not waste any time going to the Weiner Circle.
Streeterville location is good. I’m not sure what hotel? But there is shopping, wandering around Michigan ave and Gold Coast, old town, River north. Art institute.
Hugo’s Frog Bar is a classic restaurantin the Gold Coast. Love drinks at le colonial. Blue point lounge (I think it’s called—part of Shaws) has amazing seafood and fun atmosphere. Siena Tavern is good. Enjoy!

Lots of great suggestions. Thanks to all, OP