Question : Have you considered flying out of an airport besides Chicago Midway International Airport (MDW)?
Answer : Try looking for flights from O'Hare International Airport (ORD) as well. Over the next two months, flights from ORD to YQB are being booked 15% cheaper than flights from MDW to YQB. Being only 16 miles away, it's easily accessible for most.
Question : How long do most people stay in Quebec when they fly in from Chicago?
Answer : Of course you're not most people, but if you were, you'd stay roughly four days.
Question : Would you be willing to change your travel days if it saved you money?
Answer : The cheapest day to fly in December is Saturday. Being flexible with your travel days garners you even more savings during your booking.
Question : Are prices changing frequently for this route?
Answer : Prices for this trip tend to change a lot more than others. Remember, the sooner you book, the more you're able to save.