The month of February is, on average, the cheapest month to fly to Chicago from Canada, with most prices found around 298 C$. If you don’t want to visit Chicago in February, then you should wait until March to fly from Canada, when ticket prices are also cheap, with an average price of 310 C$.
We recommend purchasing flights from Canada to Chicago 60 days ahead of your departure date because this is when momondo users tend to see the best flight rates. On average, our users have found flights to Chicago for 339 C$. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Canada for as low as 255 C$ on momondo.
The cheapest day to depart on your flight to Chicago is on a Wednesday when prices can be found for as low as 344 C$. This is often the case because there is less demand to fly during this day of the week. Be sure to avoid booking your departure on a Monday as prices are generally higher than usual. According to our data, the average ticket price to Chicago on Monday is 373 C$.
Our most recent data shows that the best time of day to fly to Chicago is at noon. Flights from Canada to Chicago during this time can be as low as 328 C$. If you have a flexible travel schedule, then try to avoid flying in the evening when prices are 366 C$ on average. Flights to Chicago from Canada in the evening are generally more expensive because this time of day is more convenient for travellers’ schedules.
If you’re looking to do your hiking in warmer conditions, consider planning your flight to Chicago for September and October. Parks like Grant Park are popular hot spots in those months.
Sights like Magnificent Mile, Grant Park, and Chicago Theater are most enjoyable in months with moderate weather conditions like May or June. Plan your flight to Chicago for those months.