I am not in 'Chicagoland', but I am in IL at the same latitude and relative weather conditions, per se. My round trip commute without recharging is 72-75 miles. My drive is about half at 45-55mph and half 30-35 with mild elevation changes. I can drive it down til about 20 degrees f before I have to change plans. Fortunately, I have a rider whose home is about 10 miles closer to work, and I leave it at his house. This way we can still drive most of the trip emissions free. It is a minor inconvenience, but so is pumping gas at -10f. Plus his garage is kept at 65f and the car doesn't need much help from the heat on the way to work.
Winter range is really a difficult one to predict, because it depends on time, temp, and trip conditions. If you have a traffic jam to deal with, that adds time for the heat to run, and it eats range with a shovel at -10f. Above freezing it is more forgiving. If you can forego heat, the range can be closer to warm weather to some degree. There are posts on MNL about heating the Leaf via alternate methods.
There are people who do have more difficulty with range than myself, but I have driven my Leaf beyond 100 miles on one charge several times and beyond 200km (125 miles) once in the almost year I have owned it. Your mileage may vary greatly according to your driving habits and conditions.
My driving conditions benefit me about $200 a month in savings over an average 25mpg gas car.
If you are located in the greater Chicagoland area, you may have the advantage of en route charging stations and DCQC scattered around the landscape. These do include the inconvenience of delays, sometimes expense, and risk of nonfunctioning/ice'd stations, but those things will get better.
The Leaf is not for everyone, and please read as much about its limitations as you can before making a decision. But if you have the right circumstances and motivation, it can be a fun and comfortable car.