I can’t remember where you’re coming from, but as a Californian touring schools in Chicago and St Louis in February, I was COLD. There was lots of walking outside, both on the school tours and touristing around a bit in Chicago. My D had boots, but not winter boots and her feet were freezing even with wool socks. Plus there was icy snow on the ground and at the very least you want waterproof shoes. I DO recommend long underwear, especially if there’s any kind of wind. Also, Uniqlo has inexpensive winter coats that are very smooshable into suitcases. If I hadn’t found a drastic markdown at REI I would have gone with Uniqlo. I remember my D and I ducking into Target for cheap hats and gloves as well.
Perhaps I sound like a wimpy Californian and I’m okay with that. But why suffer on a college tour if you don’t have to? My D ultimately chose to go to college in Chicago and the weather hasn’t diminished her enthusiasm at all. She wears her long parka from REI, but rarely if ever wears her winter boots. But I think Chicago hasn’t had much snow this winter or last (Chicagoans can correct me if need be).