On this page, you can find and book flights from Vail to Chicago. This 1,599 km flight is an important link between regions, with approximately 5 weekly flights operating on this route.
The route is served by United Airlines and American Airlines. To save on your trip, check out our guides on how to get to Vail airport and how to get from Chicago airport to the city, and keep an eye on price trends in our calendar.
Below is a calendar of the lowest flight ticket prices for Vail — Chicago by day. Pick a convenient date and instantly see the fare. The cheapest flights on this route start from AED 847 in J, and the most expensive are around AED 1,110 in y. If your travel dates are flexible, the calendar will help you find the best price for your preferred period. To view round-trip fares, switch to the "Round trip" tab above the calendar, select your departure date — and the right-hand calendar will highlight the lowest prices for return flights on each day.
Vail → Chicago, average one-way price
| Month | Average price | Level | Month | Average price | Level | Month | Average price | Level |
|---|---|---|---|---|---|---|---|---|
| Jan | AED 1,795 | high | May | AED 945 | low | Sep | AED 1,087 | medium |
| Feb | AED 1,653 | high | Jun | AED 1,276 | medium | Oct | AED 945 | low |
| Mar | AED 1,039 | low | Jul | AED 1,417 | high | Nov | AED 898 | low |
| Apr | AED 898 | low | Aug | AED 1,276 | medium | Dec | AED 1,937 | high |
Some values are estimated based on seasonality.
The warmest month in Chicago is July, with average temperatures reaching 26.5°C, while January is the coldest, with temperatures dropping to -5°C. Rainfall peaks in May, while November is considered one of the driest months of the year.
According to available data, the most favorable time to fly is in January, when ticket prices start AED 847. During other periods, prices can vary significantly depending on seasonal demand and how far in advance you book.
For a comfortable trip, consider September or October, when the weather is mild and rainy days are few. If your priority is maximum savings, it is best to plan your departure for mid-winter.
Regular air service between Vail and Chicago is provided by two airlines: United Airlines and American Airlines. The route includes both direct flights and connecting options, with a total frequency of about 5 departures per week. Detailed daily schedules and aircraft types for trip planning are provided in the list below.
Flights Vail — Chicago depart from Eagle County Airport and arrive at O'Hare International Airport, Chicago Midway International Airport, Midway International Airport and Chicago Rockford International Airport. Below are pages for the cities, countries, and airports on the route: airlines, schedules, and travel guides.
With a distance of about 1,599 km, a direct flight usually takes 2 hours 10 minutes, although the exact duration depends on the flight type and weather conditions.
The main carriers operating flights between these cities are United Airlines and American Airlines.
Yes, there are direct flights on this route, but their availability and frequency depend on the season; the current schedule is always available in the block above.
Flights from Vail arrive at Chicago international airports; specific arrival terminal information can be found in your ticket details after selecting a flight.
The lowest prices are usually available when booking a month before the trip; the current minimum for upcoming dates is always displayed in our low-price calendar.
Where travelers fly most — pick a route and check prices
