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Cheap flights from Chicago to Vail from $208

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to Vail departing on 8/9. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
1 adult, Economy, 0 bags

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Chicago to Vail

Cheap round-trip flights

Enter your travel dates to find the best prices.
American Airlines Logo
12:11 pm - 6:53 pm
ORD
-
EGE
7h 42m
1 stop
American Airlines Logo
2:08 pm - 11:30 pm
EGE
-
ORD
8h 22m
1 stop
$415American Airlines
Sun, Aug 23 - Thu, Sep 3
American Airlines Logo
1:50 pm - 6:42 pm
ORD
-
EGE
5h 52m
1 stop
American Airlines Logo
2:08 pm - 10:13 pm
EGE
-
ORD
7h 05m
1 stop
$416American Airlines
Tue, Aug 18 - Tue, Aug 25
American Airlines Logo
12:11 pm - 6:42 pm
ORD
-
EGE
7h 31m
1 stop
American Airlines Logo
2:08 pm - 9:16 pm
EGE
-
ORD
6h 08m
1 stop
$452American Airlines
Fri, Aug 14 - Fri, Aug 21
American Airlines Logo
12:11 pm - 6:42 pm
ORD
-
EGE
7h 31m
1 stop
American Airlines Logo
2:08 pm - 9:16 pm
EGE
-
ORD
6h 08m
1 stop
$453American Airlines
Fri, Aug 14 - Fri, Aug 21
American Airlines Logo
8:20 am - 1:28 pm
ORD
-
EGE
6h 08m
1 stop
American Airlines Logo
7:50 am - 3:55 pm
EGE
-
ORD
7h 05m
1 stop
$454American Airlines
Mon, Aug 17 - Mon, Aug 24
United Airlines Logo
4:00 pm - 6:02 pm
ORD
-
EGE
3h 02mnonstop
United Airlines Logo
1:30 pm - 10:00 pm
EGE
-
ORD
7h 30m
1 stop
$462United Airlines
Fri, Aug 14 - Wed, Aug 19
American Airlines Logo
5:00 am - 9:53 am
ORD
-
EGE
5h 53m
1 stop
American Airlines Logo
2:12 pm - 11:48 pm
EGE
-
ORD
8h 36m
1 stop
$463American Airlines
Sun, Aug 2 - Tue, Aug 4
American Airlines Logo
6:00 am - 12:17 pm
ORD
-
EGE
7h 17m
1 stop
American Airlines Logo
8:00 am - 4:00 pm
EGE
-
ORD
7h 00m
1 stop
$489American Airlines
Fri, Sep 25 - Mon, Sep 28
American Airlines Logo
8:20 am - 1:28 pm
ORD
-
EGE
6h 08m
1 stop
American Airlines Logo
10:28 am - 6:31 pm
EGE
-
ORD
7h 03m
1 stop
$490American Airlines
Sat, Aug 15 - Sat, Aug 22
American Airlines Logo
10:40 pm - 6:59 pm
ORD
-
EGE
21h 19m
2 stops
American Airlines Logo
7:53 am - 3:00 pm
EGE
-
ORD
6h 07m
1 stop
$497American Airlines
Tue, Oct 20 - Sat, Oct 24

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American Airlines flights from Chicago to Vail

Our best American Airlines deals on Chicago to Vail flight tickets
American Airlines
Aug 23
ORD12:11 pmChicago O'Hare Intl
7h 42m
1 stop
EGE6:53 pmVail Eagle County
Sep 3
EGE2:08 pmVail Eagle County
8h 22m
1 stop
ORD11:30 pmChicago O'Hare Intl
$415
American Airlines
Aug 18
ORD1:50 pmChicago O'Hare Intl
5h 52m
1 stop
EGE6:42 pmVail Eagle County
Aug 25
EGE2:08 pmVail Eagle County
7h 05m
1 stop
ORD10:13 pmChicago O'Hare Intl
$416
American Airlines
Aug 14
ORD12:11 pmChicago O'Hare Intl
7h 31m
1 stop
EGE6:42 pmVail Eagle County
Aug 21
EGE2:08 pmVail Eagle County
6h 08m
1 stop
ORD9:16 pmChicago O'Hare Intl
$452

United Airlines flights from Chicago to Vail

Our best United Airlines deals on Chicago to Vail flight tickets
United Airlines
Aug 14
ORD4:00 pmChicago O'Hare Intl
3h 02m
EGE6:02 pmVail Eagle County
Aug 19
EGE1:30 pmVail Eagle County
7h 30m
1 stop
ORD10:00 pmChicago O'Hare Intl
$462
United Airlines
Sep 18
ORD4:00 pmChicago O'Hare Intl
3h 02m
EGE6:02 pmVail Eagle County
Sep 20
EGE7:50 amVail Eagle County
2h 58m
ORD11:48 amChicago O'Hare Intl
$515
United Airlines
Sep 12
ORD4:00 pmChicago O'Hare Intl
3h 02m
EGE6:02 pmVail Eagle County
Sep 15
EGE3:29 pmVail Eagle County
5h 23m
1 stop
ORD9:52 pmChicago O'Hare Intl
$518

momondo Fare Finder

 
Customize your flight search to find flights from Chicago to Vail that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated July 5, 2026.
Use the filters below to find and compare flights from Chicago to Vail that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoVail

ORD - EGE

ORDEGE

Chicago O'Hare Intl

Sun 8/23

12:11 pm-6:53 pm

1 stop7h 42m

Vail Eagle County

Thu 9/3

2:08 pm-11:30 pm

1 stop8h 22m

$415

ChicagoVail

ORD - EGE

ORDEGE

Chicago O'Hare Intl

Tue 8/18

1:50 pm-6:42 pm

1 stop5h 52m

Vail Eagle County

Tue 8/25

2:08 pm-10:13 pm

1 stop7h 05m

$416

ChicagoVail

ORD - EGE

ORDEGE

Chicago O'Hare Intl

Fri 8/14

12:11 pm-6:42 pm

1 stop7h 31m

Vail Eagle County

Fri 8/21

2:08 pm-9:16 pm

1 stop6h 08m

$452

ChicagoVail

ORD - EGE

ORDEGE

Chicago O'Hare Intl

Fri 8/14

12:11 pm-6:42 pm

1 stop7h 31m

Vail Eagle County

Fri 8/21

2:08 pm-9:16 pm

1 stop6h 08m

$453

ChicagoVail

ORD - EGE

ORDEGE

Chicago O'Hare Intl

Mon 8/17

8:20 am-1:28 pm

1 stop6h 08m

Vail Eagle County

Mon 8/24

7:50 am-3:55 pm

1 stop7h 05m

$454
Quickest round-trip

ChicagoVail

ORD - EGE

ORDEGE

Chicago O'Hare Intl

Fri 8/14

4:00 pm-6:02 pm

Nonstop3h 02m

Vail Eagle County

Wed 8/19

1:30 pm-10:00 pm

1 stop7h 30m

$462

ChicagoVail

ORD - EGE

ORDEGE

Chicago O'Hare Intl

Sun 8/2

5:00 am-9:53 am

1 stop5h 53m

Vail Eagle County

Tue 8/4

2:12 pm-11:48 pm

1 stop8h 36m

$463

ChicagoVail

ORD - EGE

ORDEGE

Chicago O'Hare Intl

Fri 9/25

6:00 am-12:17 pm

1 stop7h 17m

Vail Eagle County

Mon 9/28

8:00 am-4:00 pm

1 stop7h 00m

$489

ChicagoVail

ORD - EGE

ORDEGE

Chicago O'Hare Intl

Sat 8/15

8:20 am-1:28 pm

1 stop6h 08m

Vail Eagle County

Sat 8/22

10:28 am-6:31 pm

1 stop7h 03m

$490

ChicagoVail

ORD - EGE

ORDEGE

Chicago O'Hare Intl

Tue 10/20

10:40 pm-6:59 pm

2 stops21h 19m

Vail Eagle County

Sat 10/24

7:53 am-3:00 pm

1 stop6h 07m

$497

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Vail from

How to get the cheapest flight ticket from Chicago to Vail

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the typical price of a round-trip flight between Chicago and Vail?

What is the cheapest month to fly to Vail?

The cheapest month to fly to Vail from Chicago is in February. Flight prices, which tend to average around $211, 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 February, then flying in January is also cheap. Prices for this month can be found on momondo for an average of $211.

What is the cheapest day to depart on your flight to Vail?

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.

What is the cheapest time of day to depart on your flight to Vail?

Flying to Vail from Chicago in the morning is the least expensive time of day to depart. momondo users have found prices as low as $437 when looking at flights departing in the morning. Try not to purchase tickets in the evening because they tend to be around $494. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest Chicago to Vail Eagle County flight route?

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

How far in advance should I book a flight from Chicago to Vail?

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 $454 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 $349 on momondo.

What cabin class options are available on Chicago to Vail flights?

There are 3 cabin classes available to choose from on Chicago to Vail flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Chicago to Vail flights?

No. A direct flight is the cheapest option for a flight between Chicago to Vail.

When to book flights from Chicago to Vail

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago to Vail according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Chicago to Vail (CHI to EGE) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago to Vail

Best Price Found

$559

Fastest flight time

3h 02m

Direct flights

Mon, Tue, Wed, Thu, Sat and Sun

Airports in Vail

1 airport
The best flight deal from Chicago to Vail found on momondo in the last 72 hours is $559
The fastest flight from Chicago to Vail takes 3h 02m
Direct flights go from Chicago to Vail on Monday, Tuesday, Wednesday, Thursday, Saturday and Sunday. There are no airlines offering direct flights.
There is 1 airport in Vail. From Chicago there are direct flights to Vail Eagle County (EGE).
Search flight deals

Frequently asked questions about flying from Chicago to Vail

  • How far is Chicago to Vail Eagle County by plane?

    Vail Eagle County is 990.5 mi away from Chicago. Flights usually cover this in 3h 02m, depending on flying conditions and air traffic around both airports.

  • When did momondo last update prices for flights from Chicago to Vail Eagle County Airport?

    Prices for flights from Chicago to Vail Eagle County Airport refresh daily.

  • How many operators does momondo search for flights from Chicago to Vail Eagle County Airport?

  • How old do you have to be to fly from Chicago to Vail Eagle County Airport?

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Chicago to Vail Eagle County Airport.

  • What documentation or ID do you need to fly to Vail Eagle County Airport?

    The travel and health documents you'll need for your trip to Vail Eagle County Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Vail Eagle County Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Chicago to Vail?

  • What is the most popular airline from Chicago to Vail?

Best airlines flying from Chicago to Vail

Compare and see reviews for airlines that fly from Chicago to Vail with momondo
Airline
Rating
Free Cancellation
Price
American AirlinesPriceFrom $259Free CancellationRating
7.1
11,765 reviews
Search American Airlines flights
United AirlinesPriceFrom $287Free CancellationRating
7.4
9,930 reviews
Search United Airlines flights

  • United Airlines Flights From Chicago to Vail

    Across 2 United Airlines flights from Chicago to Vail this week, the average price was $464, with the best United Airlines deals starting from $287 round-trip. 9,930 users have rated United Airlines on momondo, with an average score of 7.4/10.

Traveling to a place near Vail?

Book flights to Vail if you plan to visit one of these locations
Glenwood Springs
Beaver Creek
Avon
Eagle
Rifle

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Vail?

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Chicago to Vail. Millions of users trust and use momondo every year so you are in good hands.

Can I find flights from Chicago to Vail with flexible booking policies on momondo?

Flights from Chicago to Vail with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

How can momondo help me find flights from Chicago to Vail?

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Vail from Chicago.

I’m not ready to book a flight from Chicago to Vail right now. Can momondo alert me if prices change?

If you are not ready to book a flight from Chicago to Vail now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Vail and let you know when they change.

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