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Cheap flights from Vail to Chicago 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 Vail to Chicago departing on 6/16. 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
0 bags

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Find the cheapest flights from Vail to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
American Airlines Logo
10:35 am - 8:30 pm
EGE
-
ORD
8h 55m
1 stop
American Airlines Logo
8:19 am - 1:32 pm
ORD
-
EGE
6h 13m
1 stop
$415American Airlines
Wed, Jul 29 - Tue, Aug 4
American Airlines Logo
2:12 pm - 11:32 pm
EGE
-
ORD
8h 20m
1 stop
American Airlines Logo
8:19 am - 1:31 pm
ORD
-
EGE
6h 12m
1 stop
$435American Airlines
Thu, Jun 4 - Sun, Jun 14
American Airlines Logo
2:12 pm - 11:32 pm
EGE
-
ORD
8h 20m
1 stop
American Airlines Logo
7:02 am - 1:31 pm
ORD
-
EGE
7h 29m
1 stop
$442American Airlines
Thu, Jun 4 - Tue, Jun 9
United Airlines Logo
8:00 am - 11:40 am
EGE
-
ORD
2h 40mnonstop
United Airlines Logo
4:00 pm - 6:05 pm
ORD
-
EGE
3h 05mnonstop
$449United Airlines
Sat, Jun 27 - Sat, Jul 4
United Airlines Logo
1:05 pm - 8:25 pm
EGE
-
ORD
6h 20m
1 stop
United Airlines Logo
4:00 pm - 6:05 pm
ORD
-
EGE
3h 05mnonstop
$459United Airlines
Sat, Jun 27 - Sat, Jul 4
American Airlines Logo
7:50 am - 3:39 pm
EGE
-
ORD
6h 49m
1 stop
American Airlines Logo
6:04 am - 1:32 pm
ORD
-
EGE
8h 28m
1 stop
$469American Airlines
Sat, Jun 27 - Sat, Jul 4
American Airlines Logo
8:00 am - 5:44 pm
EGE
-
ORD
8h 44m
1 stop
American Airlines Logo
11:43 am - 7:09 pm
ORD
-
EGE
8h 26m
1 stop
$511American Airlines
Mon, May 18 - Wed, May 20
American Airlines Logo
7:50 am - 3:39 pm
EGE
-
ORD
6h 49m
1 stop
American Airlines Logo
1:25 pm - 7:04 pm
ORD
-
EGE
6h 39m
1 stop
$520American Airlines
Thu, Jun 18 - Thu, Jun 25
United Airlines Logo
3:21 pm - 9:42 pm
EGE
-
ORD
5h 21m
1 stop
United Airlines Logo
10:55 am - 2:34 pm
ORD
-
EGE
4h 39m
1 stop
$542United Airlines
Wed, Sep 2 - Sat, Sep 5
United Airlines Logo
1:30 pm - 9:12 pm
EGE
-
ORD
6h 42m
1 stop
United Airlines Logo
4:38 pm - 12:21 pm
ORD
-
EGE
20h 43m
2 stops
$553United Airlines
Wed, Sep 2 - Sat, Sep 5

American Airlines flights from Vail to Chicago O'Hare Intl Airport

Our best American Airlines deals on Vail to Chicago O'Hare Intl Airport flight tickets
American Airlines
Jul 29
EGE10:35 amVail Eagle County
8h 55m
1 stop
ORD8:30 pmChicago O'Hare Intl
Aug 4
ORD8:19 amChicago O'Hare Intl
6h 13m
1 stop
EGE1:32 pmVail Eagle County
$415
American Airlines
Jun 4
EGE2:12 pmVail Eagle County
8h 20m
1 stop
ORD11:32 pmChicago O'Hare Intl
Jun 9
ORD7:02 amChicago O'Hare Intl
7h 29m
1 stop
EGE1:31 pmVail Eagle County
$442
American Airlines
Jun 27
EGE7:50 amVail Eagle County
6h 49m
1 stop
ORD3:39 pmChicago O'Hare Intl
Jul 4
ORD6:04 amChicago O'Hare Intl
8h 28m
1 stop
EGE1:32 pmVail Eagle County
$469

United Airlines flights from Vail to Chicago O'Hare Intl Airport

Our best United Airlines deals on Vail to Chicago O'Hare Intl Airport flight tickets
United Airlines
May 28
EGE1:25 pmVail Eagle County
5h 40m
1 stop
ORD8:05 pmChicago O'Hare Intl
May 31
ORD6:00 amChicago O'Hare Intl
7h 23m
1 stop
EGE12:23 pmVail Eagle County
$435
United Airlines
Jun 27
EGE8:00 amVail Eagle County
2h 40m
ORD11:40 amChicago O'Hare Intl
Jul 4
ORD4:00 pmChicago O'Hare Intl
3h 05m
EGE6:05 pmVail Eagle County
$449
United Airlines
Jun 27
EGE1:05 pmVail Eagle County
6h 20m
1 stop
ORD8:25 pmChicago O'Hare Intl
Jul 4
ORD4:00 pmChicago O'Hare Intl
3h 05m
EGE6:05 pmVail Eagle County
$459

momondo Fare Finder

 
Customize your flight search to find flights from Vail to Chicago O'Hare Intl Airport 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 April 21, 2026.
Use the filters below to find and compare flights from Vail to Chicago O'Hare Intl Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

VailChicago

EGE - ORD

EGEORD

Vail Eagle County

Wed 7/29

10:35 am-8:30 pm

1 stop8h 55m

Chicago O'Hare Intl

Tue 8/4

8:19 am-1:32 pm

1 stop6h 13m

$415

VailChicago

EGE - ORD

EGEORD

Vail Eagle County

Thu 6/4

2:12 pm-11:32 pm

1 stop8h 20m

Chicago O'Hare Intl

Sun 6/14

8:19 am-1:31 pm

1 stop6h 12m

$435

VailChicago

EGE - ORD

EGEORD

Vail Eagle County

Thu 6/4

2:12 pm-11:32 pm

1 stop8h 20m

Chicago O'Hare Intl

Tue 6/9

7:02 am-1:31 pm

1 stop7h 29m

$442
Quickest round-trip

VailChicago

EGE - ORD

EGEORD

Vail Eagle County

Sat 6/27

8:00 am-11:40 am

Nonstop2h 40m

Chicago O'Hare Intl

Sat 7/4

4:00 pm-6:05 pm

Nonstop3h 05m

$449

VailChicago

EGE - ORD

EGEORD

Vail Eagle County

Sat 6/27

1:05 pm-8:25 pm

1 stop6h 20m

Chicago O'Hare Intl

Sat 7/4

4:00 pm-6:05 pm

Nonstop3h 05m

$459

VailChicago

EGE - ORD

EGEORD

Vail Eagle County

Sat 6/27

7:50 am-3:39 pm

1 stop6h 49m

Chicago O'Hare Intl

Sat 7/4

6:04 am-1:32 pm

1 stop8h 28m

$469

VailChicago

EGE - ORD

EGEORD

Vail Eagle County

Mon 5/18

8:00 am-5:44 pm

1 stop8h 44m

Chicago O'Hare Intl

Wed 5/20

11:43 am-7:09 pm

1 stop8h 26m

$511

VailChicago

EGE - ORD

EGEORD

Vail Eagle County

Thu 6/18

7:50 am-3:39 pm

1 stop6h 49m

Chicago O'Hare Intl

Thu 6/25

1:25 pm-7:04 pm

1 stop6h 39m

$520

VailChicago

EGE - ORD

EGEORD

Vail Eagle County

Wed 9/2

3:21 pm-9:42 pm

1 stop5h 21m

Chicago O'Hare Intl

Sat 9/5

10:55 am-2:34 pm

1 stop4h 39m

$542

VailChicago

EGE - ORD

EGEORD

Vail Eagle County

Wed 9/2

1:30 pm-9:12 pm

1 stop6h 42m

Chicago O'Hare Intl

Sat 9/5

4:38 pm-12:21 pm

2 stops20h 43m

$553

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 Chicago from

How to get the cheapest flight ticket from Vail to Chicago O'Hare Intl Airport

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 Vail and Chicago O'Hare Intl Airport?

What is the cheapest month to fly to Chicago O'Hare Intl Airport?

The month of September is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Vail averaging around $406.

What is the cheapest day to depart on your flight to Chicago O'Hare Intl Airport?

The cheapest day to depart on your flight to Chicago O'Hare Intl Airport is on a Thursday when prices can be found for as low as $418. This is often the case because there is less demand to fly during this day of the week. On the other hand, Saturday is the most expensive day to depart from Vail because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $603.

What is the cheapest time of day to depart on your flight to Chicago O'Hare Intl Airport?

Flying to Chicago O'Hare Intl Airport from Vail in the morning is the least expensive time of day to depart. momondo users have found prices as low as $483 when looking at flights departing in the morning. Try not to purchase tickets at noon because they tend to be around $677. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest Vail Eagle County to Chicago O'Hare Intl flight route?

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

What cabin class options are available on Vail Eagle County to Chicago O'Hare Intl flights?

There are 4 cabin classes available to choose from on Vail Eagle County to Chicago O'Hare Intl 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 Vail to Chicago O'Hare Intl Airport flights?

You could potentially save up to 51% on your flight if you consider stops on a Vail to Chicago O'Hare Intl Airport flight.

How have Vail to Chicago O'Hare Intl Airport flight prices changed over time?

When to book flights from Vail to Chicago O'Hare Intl Airport

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

Cheap Vail to Chicago O'Hare Intl Airport (EGE to ORD) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Vail to Chicago O'Hare Intl Airport

Best Price Found

$229

Fastest flight time

2h 40m

Direct flights

Mon and Sun
The best one-way flight to Chicago O'Hare Intl Airport from Vail in the past 72 hours is $229. The best round-trip flight deal from Vail to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is $478.
The fastest flight from Vail to Chicago O'Hare Intl Airport takes 2h 40m
Direct flights go from Vail to Chicago O'Hare Intl Airport on Monday and Sunday. There are no airlines offering direct flights.
Search flight deals

Frequently asked questions about flying from Vail to Chicago O'Hare Intl Airport

  • How far is Vail Eagle County to Chicago O'Hare Intl by plane?

    A flight from Vail Eagle County to Chicago O'Hare Intl will travel around 976.6 mi. Flights usually cover this in 2h 40m, depending on flying conditions and air traffic around both airports.

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

    Prices for flights from Vail Eagle County Airport to Chicago O'Hare Intl Airport are refreshed on a daily basis.

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

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

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Vail Eagle County Airport to Chicago O'Hare Intl Airport.

  • What documentation or ID do you need to fly to Chicago O'Hare Intl Airport?

    The travel and health documents required for your trip to Chicago O'Hare Intl Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago O'Hare Intl Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

  • What is the most popular plane model from Vail to Chicago O'Hare Intl Airport?

  • What is the most popular airline from Vail to Chicago O'Hare Intl Airport?

Best airlines flying from Vail to Chicago O'Hare Intl Airport

Compare and see reviews for airlines that fly from Vail to Chicago O'Hare Intl Airport with momondo
Airline
Rating
Free Cancellation
Price
United AirlinesPriceFrom $191Free CancellationRating
7.4
9,613 reviews
Search United Airlines flights
American AirlinesPriceFrom $265Free CancellationRating
7.1
11,645 reviews
Search American Airlines flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Lake Geneva
Schaumburg
South Haven
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Merrillville
Gurnee
Rosemont
Naperville
New Buffalo
Orland Park
Oak Brook
Kenosha
Joliet
Aurora
Janesville
Racine
Hammond
Tinley Park
Elgin
Evanston

Why use momondo?

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

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Chicago from Vail.

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

Flights from Vail to Chicago 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 Vail to Chicago?

Once all potential Vail to Chicago flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

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

If you are simply researching potential flights to Chicago, momondo offers a useful price alert feature which will track prices for flights to Chicago from Vail and alert you when they change.

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