We live in a Chicago suburb. There is a very nice fairly new outlet mall that is right near the O’Hare exit off of -I294. There is also an outlet mall on I-88 in Aurora. A good winter coat will probably cost between $200 and $300. Chicago has between 1 and 2 weeks each year that are bitterly cold, think 0 F with some windchill. My D goes to college in South Bend,IN and she wears a North Face fleece jacket with some wind/water resistance. Although a heavy winter coat is great if she needs to spend a lot of time outside, much of the time college students are just going from building to building and not having a bulky coat is more important than 800 fill down
As a 30-year veteran of Chicago and the Twin Cities who has bought cold weather stuff for self, spouse, and kids, for everyday, for skiing and everything in between, I can vouch for the cheap big-box stores like Target, Kohl’s and Walmart. You shouldn’t have to spend a lot for insulation. There’s a Kohl’s on Elston Ave. in Bucktown. Target and Walmart on or near North Ave. All near one another and definitely drivable from HP.
If you want to go “LL-Bean” then consider it’s Midwest equivalent: Land’s End. Unfortunately their Elston Ave. outlet closed long ago but there are other ones scattered around the 'burbs and they have a sizable online business (if your D ever chooses to go that route).
REI is great as well. Not cheap, but at end-of-season the deals are sweet.
My advice: she isn’t XC skiing or snowshoeing to class so doesn’t need expensive sub-zero boots. A pair of knock-off Ugs will serve her well if she really wants something that goes up the leg a bit (Famous Footwear sells a popular line called Bear Paw or Bear Claw or something like that. Shearling and comfy. And affordable. The big boxes probably sell their versions as well)
The biggest risk will be slipping on ice. They’ll keep the sidewalks clear (may take a bit if major snow) but they will still be slippery. The Midwest has a habit of raining then freezing quick. So stairs and walks can get a bit treacherous. For that reason good tread is important - but she doesn’t even need boots for that. Any decent cross trainer will serve just as well.
During my seven years in HP, there was really only one time when we literally had to wade through snow to get to where we were going (headed a block or two over to Medici for dinner during the Valentines Day Blizzard of some year or other . . . ) For the most part, your daughter will be battling bitterly cold wind rather than large amounts of snow. She’ll want something that protects her from that.
It’s the salt that got my nice “California” flats, LOL. They were caked by December.
Chicago may not salt as aggressively now as they did back then. (I know that my local community in MN certainly doesn’t). But that means the “slip risk” increases.
My Arizona girl is in Chicago for college. She built up a winter wardrobe over the first year. She is also very petite. She has a Columbia coat with an inner layer that is removable–two coats in one–and a reflective lining. We bought it at the Columbia outlet here in AZ for around $100–I think an xsmall–only some styles came this small. We got her Keen winter boots on Amazon which are great, but the next summer she found a pair of Northface winter boots at Nordstrom Rack (AZ) that she loved for only $15! I haven’t done much shopping in Chicago but Since your daughter likes thrift shops, I’ve seen nice winter coats in a thrift shop in downtown Wheaton (western suburbs).
Other things we learned–hats and gloves are easy to lose–get extras, and they make good gifts. My daughter also likes fleece lined tights for an extra layer on very cold days, and has a few underarmor undershirts as well. It’s just best to dress appropriately for the cold.
As an REI fan, I recommend their website… particularly the Garage section, which is last year’s stuff (discontinued ) at nice discounts. This time of year, you can find some great deals on winter essentials. Not as much fun as going into stores and trying things on, but probably a better choice.
We let our kids wait and buy a lot of their warmer things AFTER they were on site and saw what their peers wore. There’s nothing like sticking out because your clothes “don’t fit in,” and may not be the most comfortable either. Sometimes the slight (or even major) savings just isn’t worth it.
Agree with the whole wait till you get there, but you can never go wrong with Dicks sporting goods, they have columbia and north face, known for their warmth, they also have style, sport and cool loom is what I usually go with, some prefer the bright colors too, totally personal preference but all their styles are up to date.
I would be a bit perturbed about UChicago if my kid discovered that her choice of wardrobe made it so she didn’t “fit in”. She would avoid the school if she got that sense. And I would advise her to. Hopefully that nonsense is left back at HS.
Fortunately I’m skeptical that this is an issue at the College. When we lived there, “U of C” was known for many things, but a fashion-sense wasn’t one of them 
Kids seemed to wear what they felt like.
@Mamelot sadly/happily (depending on your point of view) there are a growing number of students that actually give more than 5 seconds thought before getting dressed http://www.modachicago.com/
They are still a small minority though, most people don’t care at the best of times, and, in the dead of winter, care far more about staying warm themselves.
Judging from YikYak, Canada Goose brands you as someone who is making a conspicuous display of wealth.
My kds aren’t particularly fashion-conscious nor “follow the herd” types, but I wanted them to choose clothing they’d wear instead of stuff I chose that for some reason didn’t really work for them. It worked well for us, but different strokes for different families.
I had the same reaction re Moncler. I suspect that CG generates the reaction because it’s more popular, kinda ugly, and has those huge patches.