Leaving on a Saturday is a viable option for saving on travel. Heavily demanded days of the week can typically drive up the prices you see. Booking your travel for a less competitive day can save up to 14% on the overall cost on flights from Vail to Chicago.
Find a great deal and save up to 10% by booking at least 20 days prior to your desired departure date, rather than waiting until the week of travel. According to our data, there are a number of flights available from Vail to Chicago within the next two weeks, with the cheapest ticket starting at $137.
Flights from Vail to Chicago lean towards being more expensive in December. Prices are generally better when you fly from Vail to Chicago in April, with the cheapest ticket starting at $33.
When flying from Vail to Chicago, the time of day you fly usually plays a role in the price. Save by searching for a flight in the afternoon, which can drop the price by up to 15% versus a flight in the morning.