Best time to find cheap flights, 1% potential price drop
Price for this month
From Toronto to Chicago
Cheapest prices for Chicago Midway flights by month
At the present moment the cheapest month to fly to Chicago Midway is currently February; with January being the most expensive. Prices will vary depending on multiple factors such as booking in advance, airline and departure airports and times.
When is the best time to fly to Chicago Midway?
Choose a month below to see average flight price and weather conditions.
C$ 359 - C$ 487
1 - 29 °C
17 - 109 mm
Flying to Chicago Midway in November is usually considered the best time to fly. However, you will find other deals are always available year round. July sees the temperatures in Chicago Midway peak to their warmest. May tends, on average, to see the most amount of rainfall.
When is the best time to book flights to Chicago Midway?
The price you pay for your flight to Chicago Midway may vary depending on when you book. For the best chance of a lower fare, look to book 60 days in advance of your trip. Fares are likely to increase in the final two weeks or so before your departure date.
Days before departure
Which day is cheapest to fly to Chicago Midway?
Wednesday is currently, on average, the cheapest day to fly to Chicago Midway. Flying on Monday will result in higher flight prices.
What time of day is cheapest to fly?
Chicago Midway flights can be made cheaper if you choose a flight at noon. Booking a flight in the evening will likely mean higher prices.
Chicago Midway International Airport is developing into an important hub for domestic air travel in the United States. Last year, more than 17 million passengers passed through its gates, gaining connections to hundreds of American and international destinations.
Flights to Chicago Midway International Airport are mainly provided by Dallas-based low-cost carrier Southwest Airlines, offering cheap flights to a host of American and Canadian destinations. Most other airlines fly into Chicago’s other major airport, O’Hare.
There’s quite a lot to see and do in Chicago Midway, including a lovely central area known as Midway Boulevard. Full of shops, restaurants and cafes, Midway Boulevard is the perfect place to pull up a chair and people-watch.