Ohio I-80 turnpike is a relatively easy drive unless you get heavy and/or windy winter weather because of blowing/drifting; the road is fairly well maintained but one needs to be ready for white-out conditions in squalls. Along Lake Erie, I-90 is worse.
I dislike the PA turnpike but not familiar with true winter weather in the mountainous areas. Every time I've been on that road it rains after dark, spring, summer, and late fall. The trucks kick up water on the curves and slow grades of western PA that make visibility tricky and a bit disorienting; the comment about deer in late fall is correct as late November is peak rutting season and the hormonally crazed deer run across roads quite often to their deaths. Think if you see one, there may be more; their eyes glow red if you see them at all. Have your navigator stay alert! The turnpike is probably slower when there's a lot of snow or if cold enough and snowing enough to make de-icing with the beet juice/salt melters ineffective; otherwise okay.
Going to DC for the Iraq protest in January (*43) from Dayton on I-70, a bit more south, it was minus 13 degrees crossing into the western Appalachians with dry conditions, so not too bad but cold (how low can you go, lol); nevertheless we misjudged the time the mountains would take and were too late for the march. I-90 is an entirely different experience I'd not recommend, unless you crave adventure, because of lake effect snows.
With all that, on dry winter days, it should be a great trip; Chicago's a fabulous city to visit and shop! Keep apprised of the forecast on your travel day(s). Prepare well for winter travel with a recommended winter kit and be sure to keep your thermos full of hot coffee/soup/tea or clearing windshields, LOL, (it came in handy on I-90 once when we got temporarily stopped so the road could be cleared for travel westbound from the snow belt area on Cleveland's east side into Cleveland) and be safe!