Cheap flights from Chicago to Vail from $208

The cheapest month to fly to Vail from Chicago is in January. Flight prices, which tend to average around $369, are often lower during this time because this is during the off-season. If you aren’t able to travel to Vail during the month of January, then flying in March is also cheap. Prices for this month can be found on momondo for an average of $400.

Our data shows that Sunday is the least expensive day to fly to Vail. Tickets to fly out on this day can be as low as $331. Flights from Chicago to Vail on a Thursday will generally be more expensive and average around $476. Keep in mind that these prices on both days could fluctuate depending on the season and the demand.

Flying to Vail from Chicago in the afternoon is the least expensive time of day to depart. momondo users have found prices as low as $426 when looking at flights departing in the afternoon. Try not to purchase tickets in the evening because they tend to be around $580. Of course, these prices can vary depending on the time of year and what airport you fly to.

Fly from Chicago O'Hare Intl to Vail Eagle County for the best Chicago - Vail Eagle County flight prices

You are more likely to see cheaper flights to Vail from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to Vail for around $444 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Vail from Chicago for as low as $358 on momondo.

There are 4 cabin classes available to choose from on Chicago to Vail Eagle County flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

American Airlines and United Airlines are the most popular carriers operating from Chicago to Vail Eagle County

United Airlines, Frontier and American Airlines are the top three most popular airlines that fly to Vail from Chicago according to our data. United Airlines is the first choice among our users, with 34% of people opting to fly with this airline when traveling to Vail. Keep in mind that there are 5 different airlines that fly to Vail on a routine basis, so you have a few additional options to choose from.

As of April 2026, 2 flights take off from Chicago and land in Vail each day. The most common flight departure time for this route is 8:00AM, with 88% of daily flights taking off at noon.

As of April 2026, 14 flights take off from Chicago and land in Vail each week. The most common flight departure day for this route is Wed, with 29% of weekly flights taking off on this day.