the 2026 sales landscape is honestly exhausting. I tried checking the big retailers last week and the sites just crashed or showed fake stock constantly. its been a total disaster tbh. since you're headed to Chicago, skip the fast fashion sites. they're just pushing cheap poly-blends this year that wont do anything for the lake wind. i recently gave up on those flash sales and just went for the Filson Mackinaw Wool Cruiser Jacket. it's thick, high-quality wool that actually holds heat when it's damp. for boots, i had issues with cheaper brands leaking in the slush, so i switched to Danner Mountain Light Gore-Tex Hiking Boots. they arent cheap, but they're real gear that wont fail you. id honestly rather spend that 800 on two bulletproof items than a pile of junk that falls apart by January.

Honestly, I remember my first winter in the Midwest... i was totally unprepared. I wasted so much money on thin coats that did nothing against the wind. Last year i finally bit the bullet and got the Sorel Caribou Waterproof Winter Boots and they have been a complete lifesaver in the slush. No complaints at all, my feet stay dry and toasty even when it's sub-zero. For the heavy wool you're looking for, I've been really happy with the Schott NYC 740 32oz Melton Wool Peacoat. It's built like a tank and handles Chicago gusts no problem. I also managed to snag a Pendleton Westerley Wool Cardigan during a flash sale and it's basically a wearable blanket. If you check the direct brand sites early in the morning, like 5 AM, thats usually when the real inventory drops before the bots grab everything. Ngl, focusing on the heavy-duty brands directly is way better than browsing those aggregate sales sites.