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Cheap flights from Vail to Chicago from $191

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 3/3. 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
10:48 am - 2:36 pm
EGE
-
ORD
2h 48mnonstop
American Airlines Logo
8:05 am - 10:06 am
ORD
-
EGE
3h 01mnonstop
$331American Airlines
Fri, Mar 13 - Mon, Mar 16
American Airlines Logo
4:17 pm - 12:51 am
EGE
-
ORD
7h 34m
1 stop
American Airlines Logo
10:34 am - 12:40 pm
ORD
-
EGE
3h 06mnonstop
$341American Airlines
Fri, Mar 13 - Mon, Mar 16
American Airlines Logo
4:17 pm - 12:51 am
EGE
-
ORD
7h 34m
1 stop
American Airlines Logo
5:00 am - 11:54 am
ORD
-
EGE
7h 54m
1 stop
$351American Airlines
Fri, Mar 13 - Mon, Mar 16
American Airlines Logo
10:48 am - 2:36 pm
EGE
-
ORD
2h 48mnonstop
American Airlines Logo
8:05 am - 10:06 am
ORD
-
EGE
3h 01mnonstop
$360American Airlines
Sun, Mar 22 - Sun, Mar 29
United Airlines Logo
6:11 pm - 11:52 pm
EGE
-
ORD
4h 41m
1 stop
United Airlines Logo
7:00 am - 12:28 pm
ORD
-
EGE
6h 28m
1 stop
$365United Airlines
Fri, Mar 27 - Mon, Mar 30
Delta Logo
3:31 pm - 10:31 pm
EGE
-
MDW
6h 00m
1 stop
Delta Logo
6:00 am - 2:11 pm
MDW
-
EGE
9h 11m
1 stop
$380Delta
Tue, Mar 24 - Sun, Mar 29
United Airlines Logo
8:00 am - 12:00 pm
EGE
-
ORD
3h 00mnonstop
United Airlines Logo
7:40 pm - 9:47 pm
ORD
-
EGE
3h 07mnonstop
$383United Airlines
Sat, Mar 7 - Sat, Mar 14
United Airlines Logo
6:11 pm - 11:52 pm
EGE
-
ORD
4h 41m
1 stop
United Airlines Logo
7:40 pm - 9:47 pm
ORD
-
EGE
3h 07mnonstop
$393United Airlines
Sat, Mar 7 - Sat, Mar 14
Delta Logo
3:31 pm - 10:31 pm
EGE
-
MDW
6h 00m
1 stop
Delta Logo
6:00 am - 2:11 pm
MDW
-
EGE
9h 11m
1 stop
$406Delta
Tue, Mar 24 - Fri, Mar 27
Delta Logo
3:31 pm - 10:31 pm
EGE
-
MDW
6h 00m
1 stop
Delta Logo
6:00 am - 2:11 pm
MDW
-
EGE
9h 11m
1 stop
$409Delta
Fri, Mar 27 - Sun, Mar 29

American Airlines flights from Vail to Chicago

Our best American Airlines deals on Vail to Chicago flight tickets
American Airlines
Mar 13
EGE10:48 amVail Eagle County
2h 48m
ORD2:36 pmChicago O'Hare Intl
Mar 16
ORD8:05 amChicago O'Hare Intl
3h 01m
EGE10:06 amVail Eagle County
$331
American Airlines
Mar 13
EGE4:17 pmVail Eagle County
7h 34m
1 stop
ORD12:51 amChicago O'Hare Intl
Mar 16
ORD10:34 amChicago O'Hare Intl
3h 06m
EGE12:40 pmVail Eagle County
$341
American Airlines
Mar 13
EGE4:17 pmVail Eagle County
7h 34m
1 stop
ORD12:51 amChicago O'Hare Intl
Mar 16
ORD5:00 amChicago O'Hare Intl
7h 54m
1 stop
EGE11:54 amVail Eagle County
$351

United Airlines flights from Vail to Chicago

Our best United Airlines deals on Vail to Chicago flight tickets
United Airlines
Mar 27
EGE6:11 pmVail Eagle County
4h 41m
1 stop
ORD11:52 pmChicago O'Hare Intl
Mar 30
ORD7:00 amChicago O'Hare Intl
6h 28m
1 stop
EGE12:28 pmVail Eagle County
$365
United Airlines
Mar 7
EGE8:00 amVail Eagle County
3h 00m
ORD12:00 pmChicago O'Hare Intl
Mar 14
ORD7:40 pmChicago O'Hare Intl
3h 07m
EGE9:47 pmVail Eagle County
$383
United Airlines
Mar 7
EGE6:11 pmVail Eagle County
4h 41m
1 stop
ORD11:52 pmChicago O'Hare Intl
Mar 14
ORD7:40 pmChicago O'Hare Intl
3h 07m
EGE9:47 pmVail Eagle County
$393

momondo Fare Finder

 
Customize your flight search to find flights from Vail to Chicago 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 February 9, 2026.
Use the filters below to find and compare flights from Vail to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

VailChicago

EGE - ORD

EGEORD

Vail Eagle County

Fri 3/13

10:48 am-2:36 pm

Nonstop2h 48m

Chicago O'Hare Intl

Mon 3/16

8:05 am-10:06 am

Nonstop3h 01m

$331

VailChicago

EGE - ORD

EGEORD

Vail Eagle County

Fri 3/13

4:17 pm-12:51 am

1 stop7h 34m

Chicago O'Hare Intl

Mon 3/16

10:34 am-12:40 pm

Nonstop3h 06m

$341

VailChicago

EGE - ORD

EGEORD

Vail Eagle County

Fri 3/13

4:17 pm-12:51 am

1 stop7h 34m

Chicago O'Hare Intl

Mon 3/16

5:00 am-11:54 am

1 stop7h 54m

$351

VailChicago

EGE - ORD

EGEORD

Vail Eagle County

Sun 3/22

10:48 am-2:36 pm

Nonstop2h 48m

Chicago O'Hare Intl

Sun 3/29

8:05 am-10:06 am

Nonstop3h 01m

$360

VailChicago

EGE - ORD

EGEORD

Vail Eagle County

Fri 3/27

6:11 pm-11:52 pm

1 stop4h 41m

Chicago O'Hare Intl

Mon 3/30

7:00 am-12:28 pm

1 stop6h 28m

$365

VailChicago

EGE - MDW

EGEMDW

Vail Eagle County

Tue 3/24

3:31 pm-10:31 pm

1 stop6h 00m

Chicago Midway

Sun 3/29

6:00 am-2:11 pm

1 stop9h 11m

$380

VailChicago

EGE - ORD

EGEORD

Vail Eagle County

Sat 3/7

8:00 am-12:00 pm

Nonstop3h 00m

Chicago O'Hare Intl

Sat 3/14

7:40 pm-9:47 pm

Nonstop3h 07m

$383

VailChicago

EGE - ORD

EGEORD

Vail Eagle County

Sat 3/7

6:11 pm-11:52 pm

1 stop4h 41m

Chicago O'Hare Intl

Sat 3/14

7:40 pm-9:47 pm

Nonstop3h 07m

$393

VailChicago

EGE - MDW

EGEMDW

Vail Eagle County

Tue 3/24

3:31 pm-10:31 pm

1 stop6h 00m

Chicago Midway

Fri 3/27

6:00 am-2:11 pm

1 stop9h 11m

$406

VailChicago

EGE - MDW

EGEMDW

Vail Eagle County

Fri 3/27

3:31 pm-10:31 pm

1 stop6h 00m

Chicago Midway

Sun 3/29

6:00 am-2:11 pm

1 stop9h 11m

$409

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

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 cheapest day to depart on your flight to Chicago?

The cheapest day to depart on your flight to Chicago is on a Thursday when prices can be found for as low as $295. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Vail to Chicago for around $518.

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

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from Vail to Chicago during this time can be as low as $203. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $580.

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

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

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

There are 4 cabin classes available to choose from on Vail Eagle County to Chicago 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 flights?

You could potentially save up to 36% on your flight if you consider stops on a Vail to Chicago flight.

When to book flights from Vail to Chicago

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

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

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

Best Price Found

$305

Fastest flight time

2h 53m

Direct flights

Mon, Tue, Wed, Thu, Sat and Sun

Airports in Chicago

3 airports
The best one-way flight to Chicago from Vail in the past 72 hours is $305. The best round-trip flight deal from Vail to Chicago found on momondo in the last 72 hours is $331.
The fastest flight from Vail to Chicago takes 2h 53m
Direct flights go from Vail to Chicago on Monday, Tuesday, Wednesday, Thursday, Saturday and Sunday. There are no airlines offering direct flights.
There are 3 airports in Chicago. From Vail there are direct flights to Chicago O'Hare Intl (ORD).
Search flight deals

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

    Chicago is 990.5 mi away from Vail Eagle County. A reasonable flight in good conditions will take 2h 53m.

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

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

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

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

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, 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.

  • What documentation or ID do you need to fly to Chicago?

    The travel and health documents you'll need for your trip to Chicago 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 Chicago. 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 Vail to Chicago?

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

Best airlines flying from Vail to Chicago

Compare and see reviews for airlines that fly from Vail to Chicago with momondo
Airline
Rating
Free Cancellation
Price
United AirlinesPriceFrom $191Free CancellationRating
7.4
9,257 reviews
Search United Airlines flights
American AirlinesPriceFrom $331Free CancellationRating
7.2
11,254 reviews
Search American Airlines flights

  • United Airlines Flights From Vail to Chicago

    United Airlines is one of the most popular airlines flying from Vail to Chicago, operating 10 flights/week on average for this route. A good United Airlines flight deal for Vail to Chicago starts from $191 round-trip, up to an average price of $486. Our users have rated United Airlines at 7.4/10.

  • American Airlines Flights From Vail to Chicago

    The best American Airlines deal for Vail to Chicago flight tickets found on momondo in the last 72 hours was $331, round-trip. It should be noted that an average American Airlines flight deal for this route in this time was higher, at $476 round-trip. American Airlines operates 4 flights out of Vail into Chicago in an average week, so prices vary by time and availability. 11,254 American Airlines reviews by users on momondo have scored the airline at 7.2/10.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Saint Joseph
Portage
Lansing
Schererville
Valparaiso
Munster
Crown Point
Chesterton
Monticello
Porter
Griffith
Saint John

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?

Yes. momondo enables you to select and highlight flights to Chicago from Vail with this policy.

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

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Vail to Chicago.

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

Of course. momondo tracks the price of Vail to Chicago flights. All you need is a valid email address and we will do the rest; it is that quick and easy.

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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago
Chicago Midway Airport
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport