I have been using a similar strategy for a few years now and it works well for me. Honestly, you should probably just join the free loyalty tiers to get that early access window. Inventory for winter gear is always tight in November, and I have no complaints about paying a slightly higher price early to ensure I actually get my size. For Chicago, you definitely want to secure a high-quality layer like the Patagonia Frozen Range Parka GORE-TEX Down or the Pendleton Wool Peacoat 100% Virgin Wool. I was very satisfied with how my Sorel Caribou Waterproof Winter Boots held up during the last polar vortex, and those always sell out fast. Tbh, waiting for that extra 10 percent discount on Friday isnt worth the stress of seeing everything go out of stock. It is a more methodical approach to buy the heavy hitters during early access and save the leftovers for the midnight drops.

Building on the earlier suggestion, definitely wait for the midnight drop to grab the Schott NYC 740 32oz Melton Wool Naval Peacoat! It's amazing for Chicago and a fantastic value, tbh!

Like someone mentioned, waiting for the midnight drops is a classic strategy, but I have to disagree slightly when it comes to winter gear. In my experience, those doorbusters are getting much harder to snag because inventory is already depleted by Friday. Over the years, I have tried many different ways to save money, and honestly, the stress of the midnight rush just isnt worth it for such an important move. For your budget, you really cant go wrong if you just get any insulated parka from The North Face during the early loyalty week. I have found that their early deals are usually within a few dollars of the Friday price anyway. Methodically securing your size early is way better than ending up with nothing. Same goes for footwear. Just grab some durable leather boots from Red Wing Heritage and you will be fine for those Chicago winters. It is much more practical to pay slightly more for guaranteed warmth than to gamble on a code.