<p>I've lived in SO MANY cold, unpleasant places with bad winters, including OP's requested comparison between Chicago and Syracuse. My overall feeling is they are more alike (in lifestyle) than different, regardless of splitting hairs over windchill factor, average temps, and snowfall. It's a matter of DECIDING you like the cultural/resource offering of the place you live and that it's worth putting up with bad winter weather to get it. Also, everyone forgets to mention how drop-dead perfect these places are every summer, but college students often aren't there to enjoy it then.</p>
<p>I've lived in Boston, Cape Cod (raw Atlantic seacoast storms, Noreasters), New Hampshire, the Catskill MTs. of upstate NY, Buffalo NY, and a suburb south of Chicago over near Gary, Indiana. Also I lived in Ottawa, Canada which is north of Moscow in terms of latitude and much colder than either Toronto or Montreal. Plus there was a time in Michigan. I only had one nice winter weather place in my life (I thought--Austin, Texas) but it, too faced some freezing rain days in January.</p>
<p>The point is: you change your lifestyle to accommodate winter. Everyone does, whether that means young people taking up winter sports or old people saving all their knitting/sorting/organization projects for the winter months. You can't move around as freely. You appreciate, tremendously, the mobile days from May-October. When winter begins, it's rather charming as it's marked by Halloween, Thanksgiving, Christmas. The problem for me is it's LENGTH, not its intensity, so that by March and April I have to fight off depression and I notice people very cranky throughout the community. </p>
<p>College kids do not have to deal with some of the issues that homeowners struggle with, such as plowing out their cars or paying heating bills. Some of this is to consider it all as a college person, not their parent, would live. They don't have to buy homes here. They do have to use airports so might have trouble flying home on bad-luck winter days, but if they don't bring a car there are NO day-to-day issues. </p>
<p>IN answer to the OP, my experience of winter outside of Chicago was that it was very cold, wet and windy from the Lake on some days, so that it was unpleasant to walk from place to place, yet still I did so. I wore a scarf. I drank hot chocolate. I dressed in layers. </p>
<p>That's essentially what I did also in upstate NY (Catskills, now Buffalo), so that resembles Syracuse. I don't remember one being a "better" winter than the other, honestly. I just braced myself for winter in both places, piled up extra craft and reading projects, and toughed it out. When I was younger I'd cross-country ski, and that made me look forward to each snowfall. Skiing will inverse your entire relationship to snow, such that you cheer when it snows.</p>
<p>The big differeence in Ottawa was that the snow came down in November and kept a solid ground cover of white until Spring, meaning mid-May, except for a one-week "January Thaw." In the U.S., by contrast, there are snow events, but it melts back to green several times each winter, so the landscape around you changes more frequently than in Ottawa. </p>
<p>A grey day is warmer than an extremely cold day, because when it's zero degrees F outside (as in Canada), it's too COLD for clouds, so the freezing air is made bearable by a brilliant blue sky. Some weeks in winter felt like a trip outside was walking into a walk-in freezer.</p>
<p>When clouds come along, as in Syracuse, it's usually between 20-30 degrees, so yes it's gray but it's also more manageable, walkable winter temperature. </p>
<p>If I had to choose about colleges, I'm sure I'd consider both Chicago and Syracuse difficult weather-wise. Both airports often are impacted. So choose by the program you want, not the weather, even if Syr has 3x the snowfall, IMHO</p>