One of the great things about living in the midwest is that canoeing and kayaking can be a year-round sport - as long as you're properly prepared for the elements. For midwestern paddlers, that means owning some essentials that will keep your body heat in while keeping the cool water out.
KEEPING HEAT IN
A pair of jeans and a tee may work for summer canoeing, but in fall and spring, that same ensemble is one capsize or accidental slip into the water away from being a potential disaster, since cotton has no insulating capacity when wet, and, worse, will actually suck heat out of your body.
Instead, you'll want to underdress with nylon or other insulating/quick drying inner layer, and layer up to meet the air temps. A neoprene layer is never a bad idea, whether a shorty style wetsuit (for water in the 60s) to a farmer john/jane (water in the high 50s) to a full arm and leg suit (water in the low 50s and cooler).
For those who want some flexibility, NRS' "Hydroskin" suits offer soft plush linings under 1.5mm to .5mm neoprene material, making them much more comfortable than a regular nylon-lined wetsuit.
KEEPING WATER OUT
Spraywear is proper for days where you're going to be encountering wind-driven spray but the water isn't necessarily deadly-cold: a dry suit is for days when any immersion would mean a life-threatening conditions (and a semi-dry suit splits the difference between those two extremes).
For cool, but not cold conditions, a set of spray pants and a spray top, with or without hood, should be fine, as long as you're underdressed for possible immersion (a wetsuit under your spray gear, for example). Examples would be the NRS Endurance Splash Pants and the hooded High Tide paddling jacket, which would cover most October and November conditions on rivers and lakes around Chicagoland.
WHEN IT GETS EXTREME...
When the water and/or air temps are below 50 degrees, you're into Drysuit territory. A drysuit like the NRS Navigator uses a combination of watertight seals around the neck, wrists, and ankles to keep all cold water away from direct contact with your skin.
For those who can't afford a full-on drysuit, a semi-dry paddling suit like the NRS Explorer gets you water tight wrists and ankles (with built-in socks) with a neoprene, rather than latex, neck seal - protection enough for all but the most extreme conditions.
With a drysuit, a paddling buddy, and the proper self-rescue and assisted rescue skills and gear, there's no reason why you can't be paddling well into winter time around the midwest, and it opens up your paddling experiences to some of the quietest, most peaceful outdoors experiences available.
FEET AND HEADS AND HANDS
For relatively mild fall and winter days, we actually like to use the same insulating beanie we wear under our cycling helmet, but when the water's below 50 or you're out on Lake Michigan, a full on Storm Hood is the way to go.
Canoeists and kayakers will differ a little bit in terms of their hands - canoeists will usually prefer five-finger neoprene gloves like the NRS Maverick, where kayakers can go with mitts or poagies (neoprene or nylon covers that attach to your kayak paddle shaft, and allow you to slide your hands in and out easily).