Flights from Windsor to Chicago are generally found to be more expensive on Wednesday. This shouldn't discourage you from searching, as you can still find great deals by being flexible with your options. Use our search form to find deals on tickets to Chicago.
To save up to 86% on this flight, we recommend booking at least 34 days prior to travel. The price may fluctuate and will likely increase closer to your departure date. Users on Cheapflights have found tickets from Windsor to Chicago from C$ 436 1-2 weeks out and tickets from C$ 590 for flights departing within the next 72 hours.
Due to multiple factors, expect to potentially pay more when booking in January. For low rates, April can be a great choice for travel to Chicago. Flights to Chicago from Windsor in April are about C$ 317 on average during April, but can be found for as low as C$ 240.
It’s optimal to fly from Windsor to Chicago at noon. By choosing this option you can save up to 10% on the cost of your flight, compared to a flight in the morning.
Our data indicates that the weather will be 29 °C on average in the month of July. The temperature in Chicago is typically the same as in Windsor. If you're traveling when the temperature is at its warmest, push to plan early, as flight price and availability will have an impact on your travels. For the best results, search for flights well in advance or after peak season.