My d’s coming from Long Island went to school in Boston area and in Rochester. They both started the year off with fleeces from North Face but they also needed winter jackets like a warm pea coat or something similar as well as a longer down coat. Dorms for the most part are overheated but when you come back from winter break when the heat has been on low for several weeks and it is frigid outside, it does take some time for the building to warm up. They both had Merrill’s as well as rainboots. Duck boots from LL Bean are good and Timberlands are good too.
By looking at LL Bean, you can see the actual temperature ratings. Maybe Lands End, as well.
Mine went to college in Maine and were fine with Northface fleece for fall and sweatshirts. Then a down parka for later. You want that just large enough to layer a sweater under, if needed. (Some parkas are cut close for some thermo reason.)
Don’t wait to get there, selections can go fast. And your son will be a newbie to this. There are some online discounters with the name brands. You just don’t need one of those $800 sorts, lol. (It’s another good reason to look at LLB and LE, to see reasonable price ranges.)
Dorms are usually warm enough. Yes to the blanket and comforter. He can also take a light sleeping bag, the sort that rolls up small. Yes to a good scarf, I’d say wool. It’s with it to invest in great gloves, the sort skiers might wear, none of the flimsy ones.
Our kids who are used to the weather up north may be hardier.
Don’t get an electric blanket or heated mattress pad until you confirm they’re allowed. Many schools don’t want them used.
DD is a sophomore at Marquette in Milwaukee, we live in Houston (Hubby is from Rochester, I am from NE Ohio; we know cold) and DD lived in Northern VA for a few years so isn’t completely unaware of what snow/cold can be like.
LLBean boots (DD used Sperry boots last year…there is no comparison, buy the llbean), she also has a pair of thinsulate lined waterproof hiking type shoe/boot things which get a fair amount of use (DD says Timberlands for dudes) and a pair of Columbia snow boots that also get worn in Jan/Feb (as a girl she has Uggs that are nice in the Fall when it is cool and dry). Use boot socks. She wears Birkenstock (dudes do too but also addidas/nike slides) sandals in early fall and late spring cuz you can pair sock with them if necessary and not look like a dork. She and her Wisconsin native roomie both wear a Columbia Parka with zip in/out liner (that covers the butt AND has a hood). She broke down and bought a Patagonia fleece this year which she likes better than the NorthFace fleece she had last year. Make sure at least one hat is thermal lined not just thickly knit. She claims to not use gloves/mittens unless it is below 20 (I assume her hands are pulled up into her sleeves and stuffed in her pockets most of the time). Flannel shirts are popular. DD says “layers are your friend and scarves, scarves, scarves, just use the dang scarf, you won’t regret it”
She has never complained her dorm was cold, but does say it is too dry; be prepared for nose bleeds/chapped lips with gel nasal spray and something better than Chapstick or Eos. DD says to remember to bring a jacket when it is between 50 and 60, it is a weird temp zone, you will be cold in the north and happy you remembered the jacket even though your northern buds are ok without the jacket. Her #1 bit of advice… schedule your classes in a block where you do not have time to go back to your dorm inbetween classes because “when it is 20 degrees out you will not want to go out again, you will but it will suck, so just don’t do that to yourself, schedule the block even if it means an 8am class”
“Our kids who are used to the weather up north may be hardier.”
"DD says to remember to bring a jacket when it is between 50 and 60, it is a weird temp zone, you will be cold in the north and happy you remembered the jacket even though your northern buds are ok without the jacket. "
So true! Our D grew up in MN and said everyone at UChicago started pulling out the jackets in October while she was still wearing just a T shirt. She had a very light down coat from Costco which worked just fine through end of first quarter. No hat or gloves. I’m sending her back tomorrow morning with something a bit more substantive and also a pair of Uggs. She used the knock-offs all throughout high school. They probably will get a bit trashed from the salt and mud but she loves the way they feel. The thinsulate hiking boots are a very sensible idea - my kid would never wear them, however. She prefers regular socks and shearling. But regardless of type of boot, socks are a must, unless you like stinky boots . . .
Mostly he needs the 6 months free Amazon Prime account he will get as a new college student. Don’t try to buy too much ahead. He may want certain brands or items once he gets there. Others may not be cool (example, LL Bean’s cache varies). Make sure he has long casual pants (jeans or whatever he wears, a couple sweatshirts, a rain resistant jacket for the fall with a hood). I’d let him get coat, gloves, hat, shoes after he gets there. You can give him some stuff for Xmas, too.
Lots of good suggestions above. My $0.02: dorms will be just fine. Housing cranks the heat up to 11 the minute students get back.
For the past 1.5 years, I’ve been using silk sheets and a comforter when it gets cold, and I had to crack open my window to cool my room last winter. Haven’t seen any electric blankets/extra space heaters in my dorm. These might be necessary if a student ends up with the one room in a hall where something’s off about the heating or insulation, but I would hold off on buying anything until and unless this turns out to be the case.
Last year we had an extremely warm winter by historical standards, so my experience is a tad idiosyncratic, and I may actually need to keep my window closed for a full week this year. Still, the only thing that needs to be heated above dorm temperature is a room’s occupant - and warm clothes/blankets can generally take care of that even when outside temperatures are frigid.
As I type this, it’s 5 degrees below zero outside Daley’s Restaurant, and the wind chill makes it feel a dozen degrees colder than that. I’m wearing an old ski jacket that isn’t particularly warm as jackets go, a t-shirt underneath, and a pair of jeans; when dorms open a half-hour from now I’ll walk half a mile to B-J in this outfit. That’s as long as any walk most people will face on campus, and most students don’t bring a suitcase to class. I am grateful for my ushanka, which keeps my ears warm, and wish I had a scarf to cover my nose. I highly recommend both. I’m also glad for my gloves, which will ensure I reach B-J with most of my fingers still attached. In my experience, everything else is optional.
Lands End is having a one day sale…50% off one item, not sure what conditions there are.
But it might be worth it for some of you who are looking at winter coats to take a look.
My kid went from Arizona to Chicago for college. Do your shopping for winter gear between now and February or so to catch the clearance deals. D has a Columbia 3 in 1 coat that zips apart into a lightweight jacket. It has the reflective stuff on the inside for retaining body heat. She loves it. Also a lined knit cap or a trapper hat. Good winter boots. For gloves she just has lots of pairs of the same color magic gloves. She’s always losing one and can easily replace that way. She probably has a better pair too but doesn’t use them much. She also wears leggings under jeans when it’s really cold. She has some scarves and some good warm sweaters. D says don’t overdo it. He can always add to his wardrobe once he’s there. For bedding we sent her with typical dorm stuff and added a down comforter from Amazon once the weather got colder. He’ll be arriving in summer so there’s time. We’ve been able to find good gear in Arizona, it’s just available in smaller quantities, but sometimes at great prices as well. we found a beautiful pair of Timberland winter boots at Nordstrom Rack in July for $15.
In her experience, the style of dress in Chicago is a bit more dressed up than it is in Arizona. Her wardrobe has shifted over time to reflect that.
I second several comments above to the effect of don’t be over-concerned about the Chicago winter. I came to Chicago from Texas many years ago and brought with me a light jacket, a sweater or two and nothing special in the way of footgear. I must also have had a cap and pair of gloves, though don’t remember wearing them much. I lived south of the Midway all four years, so crossed that iconic bit of greensward (or whitesward) several hundreds of times in all sorts of weather. I remember being a bit chilly at times, but it was of short duration. I was warmer in the dorm and in most buildings in Chicago than I had been during cold weather snaps in Texas, where there was little central heating. In one of those years (1967 I believe) we got the epic snowfall that still holds the city record. There were many scenes of students leaping from windows (first floor ones!) into gigantic drifts of snow, of winding their way through tunnels of head-high snow - and of course snowball fights galore. What fun.
Every time cold(er) weather clothing has been a thread, I pointed out that it doesn’t get terribly cold before December break.
Not this year.
IMHO, every parent (especially those from the warmer states) will fret about whether their kid will survive Windy City supposedly brutally cold winter while the kids will shrug and go to the Main Quad or Reg in any jacket they have on. Indeed I think the boys will want to prove their toughness by not wearing the warmest clothing available ;). I am not starting a political debate but the trend is that Chicago winter has been warmer for the last 15 years. Polar vortex in 2014 did not happen every year. So OP’s kid will be fine whenever and wherever he gets his winter gear.
Among the items I recommend (Post #18), however, I would advise definitely getting a pair of snow boots first. A short walk from the North to Eckhart in subzero wind chill is not likely to cause major damage to any college kid. But a badly sprained ankle or worse a broken fibula from slipping on icy sidewalk will be a major inconvenience for the Winter Quarter.
Winter boots go on sale around this time of year on sites like Sierra Trading Post or Merrell. There should be enough choices for all types of budget.
@DunBoyer I had to google “ushanka” - looks awesome! Will definitely find one of those. And thanks, @bjkmom for the tip on the Land’s End sale.
This has been really helpful. All the posts have had suggestions for things he doesn’t have. It’s great to know what is needed and what’s not.
“UShanka” is better known as the Grumpy Old Men hat. Or something you wear ice fishing. Or that funny hat that Francis McDormand wore in Fargo. Call it what you want, it’s warm. One of my kids purchased one for skiing “up north” - ironically, the weather on the north shore of Lake Superior has been warmer than in the Twin Cities! Go figure!
My first autumn quarter at UChicago I still had my mid-80’s CA clothes (cotton stuff made by Esprit, a sweatshirt or two cut to fall off the shoulder, thin pointy flats, no socks . . . ). I remember that by 10th week I was actually uncomfortably cold inside the classroom. Wearing a warm pair of socks alone would have helped. Three weeks later, everyone showed up for Winter Quarter looking like the Michelan Man. Those were the days of very puffy parkas.
One fun fact about midwest winters - many of the locals will continue to wear shorts till they absolutely can’t. It’s amazing how low the temp. has to go for them to put on a pair of long pants.
My kid: “Only parents wear LL Bean and Land’s End”. I know it isn’t quite true, and there are exceptions, but really… the sales will be happening in the fall on those websites as well if that is what the kid thinks they need when they get to campus. Same with things like space heaters, etc.
“My kid: “Only parents wear LL Bean and Land’s End”.”
That’s why I’m asking here - hoping to get this good advice from the actual UChicago peeps. I figured if I guessed about this stuff myself, he was at risk of being dressed like a middle aged woman rather than the rest of the undergrads. 
Fear not – my daughter is going back to University of Chicago dressed in LL Bean. The only other person I know who actually buys LL Bean is her granddad. But if my kid really wanted to “dress cool”, she probably would not have shown up at the University of Chicago in the first place.
I would agree in general clothing wise, only parents wear LLBean. But, according to DD the LLBean duck boot is the exception and quality wise it is unmatched.
Yeah, my kid got the LL Bean boots last winter in Chicago (caution: some run >1 size large, so either buy them in a store or commit to sending them back if they don’t fit). Swears by them for walking across campus. Also remember storage space. At some point last year she brought the winter stuff home and picked up summer stuff. Might have been Spring break. And I’d let them do the shopping; maybe buy one or two things as presents.
@milee30 Try REI for a good selection of coats - Patagonia, The North Face, Arc’teryx…my daughter who is a Second Year likes them for jackets and fleeces. She’s a fan of layering, and was taught from an early age that there is no bad weather, only bad clothing choices. We lived in Bavaria for most of her life, so she’s used to cold weather and snow, although the winds of Chicago, especially while crossing the Midway, can be brutal.
Your son might find flannel or fleece lined jeans useful. My daughter looked at them (at Land’s End, no less!), but opted for new silk pants and undershirts to wear under her clothing. She did suggest a blanket scarf because not only can it be wrapped around the neck/head/face for warmth, when folded up it makes a great pillow for when she needs a power nap during long study sessions at the Reg.
Last year for Christmas, we got her a rechargeable hand warmer, which she ended up using quite a bit. Her hands are cold 10 months out of the year! 
She got back to campus about an hour ago and is now out running errands. The temp is in the single digits, but she swears it doesn’t feel too bad.
I will be 12 below at my son’s school on Saturday. He is going to learn what I mean by “real gloves”, not those dollar store knit things he had as a kid in the south.