Cheap flights from Chicago to Vail

Flights overview

Useful information for finding cheap flights from Chicago to Vail and booking your next trip
Cheapest round-trip flights $329
American Nonstop 4 hr Thu, Apr 2 — Sun, Apr 5
The cheapest round-trip flight from Chicago to Vail is currently $329
Cheapest one-way flight $208
American 1 stop 9 hr Sun, May 10
The cheapest one-way flight from Chicago to Vail is currently $208
Last-minute weekend getaway $549
American Nonstop 4 hr Thu, Mar 12 — Sun, Mar 15
The cheapest last-minute weekend getaway from Chicago to Vail is currently $549
Cheapest business class flights $829
United 1 stop 8 hr Thu, May 28 — Mon, Jun 1
The cheapest business class round-trip flight from Chicago to Vail is currently $829
Fastest flight 3 hr 1 min The fastest nonstop flight from Chicago to Vail takes 3 hr 1 min
Nonstop flights Every day There are direct flights on this route every day.

When is the cheapest time to fly?

The cheapest month to fly from Chicago to Vail is typically June. The most expensive month to fly is typically July.
June
Cheapest
Typical prices: $295–425
July
Most expensive
Typical prices: $400–670

Popular airlines from Chicago to Vail

  • United
    Nonstop
    from $349
    Typical price: $325–570
    14 weekly nonstop flights
    ORD - EGE Every day
    910 weekly connecting flights
    ORD - EGE Every day
  • American
    Nonstop
    from $329
    Typical price: $345–750
    14 weekly nonstop flights
    ORD - EGE Every day
    279 weekly connecting flights
    ORD - EGE Every day
  • Delta
    from $569
    Typical price: $375–1,450
    441 weekly connecting flights
    MDW, ORD - EGE Every day
  • Alaska
    from $1,232
    Typical price: $420–1,100
    12 weekly connecting flights
    ORD - EGE Every Wed, Fri, Sat, Sun

Popular airports near Chicago

  • Chicago O'Hare International Airport (ORD)
    Chicago United States 26 min 16 mi
  • Chicago Midway International Airport (MDW)
    Chicago United States 25 min 9 mi
  • Milwaukee Mitchell International Airport (MKE)
    Milwaukee United States 1 hr 24 min 75 mi
  • Indianapolis International Airport (IND)
    Indianapolis United States 2 hr 59 min 165 mi

Popular airports near Vail

  • Denver International Airport (DEN)
    Denver United States 2 hr 2 min 91 mi
  • Eagle County Regional Airport (EGE)
    Vail United States 39 min 29 mi
  • Aspen/Pitkin County Airport (ASE)
    Aspen United States 1 hr 45 min 39 mi
  • Colorado Springs Airport (COS)
    Colorado Springs United States 2 hr 50 min 106 mi

Frequently asked questions about flying from Chicago to Vail

The cheapest flights from Chicago to Vail are usually in June. Typical ticket prices in June range from $295 to $425.
The cheapest round-trip flight from Chicago to Vail recently found on Google Flights was with American from $329. The cheapest one-way flight was with American from $208.

Some of the cheapest round-trip deals we found with different airlines:
  • The cheapest United flight from Chicago to Vail is $349, flying from Apr 23 to Apr 26.
  • The cheapest American flight from Chicago to Vail is $329, flying from Apr 2 to Apr 5.
  • The cheapest Delta flight from Chicago to Vail is $569, flying from Mar 12 to Mar 15.
  • The cheapest Alaska flight from Chicago to Vail is $1,232, flying from Mar 13 to Mar 15.
The cheapest round-trip flight from Chicago to Vail starts at $329 from Thu, Apr 2 to Sun, Apr 5. The cheapest one-way flight starts at $208 and departs on Sun, May 10.
3 hr 1 min is the shortest flight time from Chicago to Vail.
Cold, snowy Dec–Mar (peak ski season) is the most popular time to visit. The Vail Film Festival (Mar/Apr) draws movie buffs for screenings, panels, parties and late-season skiing. Mild and sunny midsummer (Jul–Aug) is another busy travel period, with outdoor activities like hiking and rafting, plus open-air cultural events like the Bravo! classical music festival (Jul–Aug) and the Vail Dance Festival (Jul–Aug).
It's easy to use Google Flights to find the cheapest days to fly from Chicago to Vail.
Just click the Departure label near the top of the page to open the calendar. Choose a start date and a return date to see how the round-trip fare changes on those specific days.
Adjust the trip type to see one-way fares. The cheapest available flights are highlighted and easy to spot. Once you settle on dates, click the Search button to see flight options and book the deal.

You can also turn on price tracking to get alerts if the price changes for a route or flight.
What counts as the best airline for your flights from Chicago to Vail really depends on your individual needs. You may have a favorite carrier or a loyalty program you like, but price, convenience, and airports served also come into play. Flexibility and booking terms – Can you change flights if you want to stay longer or get a refund if you have to postpone your trip? – are also factors that help determine which airline is best to fly from Chicago to Vail.

In terms of nonstop flights, United is the most popular. United offers 14 nonstop flights and 910 connecting flights per week. United flies from Chicago O'Hare International Airport (ORD) to Eagle County Regional Airport (EGE) .

Other popular airlines flying from Chicago to Vail are:
  • American offers 14 nonstop flights and 279 connecting flights per week. American flies from Chicago O'Hare International Airport (ORD) to Eagle County Regional Airport (EGE) .
  • Delta offers 441 connecting flights per week. Delta flies from Chicago Midway International Airport (MDW) , Chicago O'Hare International Airport (ORD) to Eagle County Regional Airport (EGE) .
  • Alaska offers 12 connecting flights per week. Alaska flies from Chicago O'Hare International Airport (ORD) to Eagle County Regional Airport (EGE) .
The number of connecting flights refers to distinct flights with at least one stop between Chicago and Vail.
The cheapest round-trip flight from Chicago to Vail recently found on Google Flights was with American from $329. The cheapest one-way flight was with American from $208.

Some of the cheapest round-trip deals we found with different airlines:
  • The cheapest United flight from Chicago to Vail is $349, flying from Apr 23 to Apr 26.
  • The cheapest American flight from Chicago to Vail is $329, flying from Apr 2 to Apr 5.
  • The cheapest Delta flight from Chicago to Vail is $569, flying from Mar 12 to Mar 15.
  • The cheapest Alaska flight from Chicago to Vail is $1,232, flying from Mar 13 to Mar 15.
American and United fly direct from Chicago to Vail.
  • There are 14 United direct flights from Chicago to Vail per week. Flights are available every day.
  • There are 14 American direct flights from Chicago to Vail per week. Flights are available every day.
Use the Stops filter while searching for flights, to see only nonstop options in your results.
The cheapest last-minute deal between Chicago and Vail at price $549 is offered by American from Thu, Mar 12 to Sun, Mar 15.
American and United fly direct from Chicago to Vail.
  • There are 14 United direct flights from Chicago to Vail per week. Flights are available every day.
  • There are 14 American direct flights from Chicago to Vail per week. Flights are available every day.
Use the Stops filter while searching for flights, to see only nonstop options in your results.
There are direct flights from Chicago to Vail on a daily basis.
The cheapest direct (nonstop) round-trip flights between Chicago and Vail start at $329 from Thu, Apr 2 to Sun, Apr 5 with American.
It's easy to find nonstop flights with Google Flights! Once you've searched for flights from Chicago to Vail, just select the nonstop flights only option in the 'Stops’ filter in the search form and view all available direct flights and their prices.
The cheapest business class round-trip flights between Chicago and Vail start at $829 from Thu, May 28 to Mon, Jun 1 with United.
The cheapest economy class round-trip flights between Chicago and Vail start at $329 from Thu, Apr 2 to Sun, Apr 5.
To book business class trips from Chicago to Vail, look for the default Economy selection at the top, and change it to your desired cabin class such as Premium Economy, Business Class, or First Class. You can then select your departure and arrival dates, consider available options, and book your business travel.

You can also adjust the trip type to view one-way fares.
The best last-minute getaway deal for the next weekend between Chicago and Vail starts at $549 from Thu, Mar 12 to Sun, Mar 15 with American.
The cheapest last-minute deal between Chicago and Vail at price $549 is offered by American from Thu, Mar 12 to Sun, Mar 15.
To find last-minute flight deals from Chicago to Vail, start by entering the city names, select the desired departure and return dates, and hit the Search button to view flight options.

You can check for last-minute flights for the same day or adjust the trip type to see one-way fares.

Search more flights

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