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Cheap flights from Vail to Chicago from $141

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 2/3. 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.
United Airlines Logo
12:30 pm - 4:25 pm
EGE
-
ORD
2h 55mnonstop
United Airlines Logo
9:15 am - 11:27 am
ORD
-
EGE
3h 12mnonstop
$291United Airlines
Thu, Feb 5 - Mon, Feb 9
United Airlines Logo
3:30 pm - 11:59 pm
EGE
-
ORD
7h 29m1 stop
United Airlines Logo
12:45 pm - 2:52 pm
ORD
-
EGE
3h 07mnonstop
$301United Airlines
Fri, Feb 13 - Tue, Feb 17
United Airlines Logo
3:30 pm - 10:52 pm
EGE
-
ORD
6h 22m1 stop
United Airlines Logo
7:10 am - 12:33 pm
ORD
-
EGE
6h 23m1 stop
$311United Airlines
Fri, Feb 13 - Tue, Feb 17
American Airlines Logo
12:01 pm - 4:01 pm
EGE
-
ORD
3h 00mnonstop
American Airlines Logo
9:01 pm - 10:17 am
ORD
-
EGE
14h 16m2 stops
$329American Airlines
Wed, Dec 31 - Wed, Jan 7
American Airlines Logo
3:50 pm - 12:16 am
EGE
-
ORD
7h 26m1 stop
American Airlines Logo
9:01 pm - 10:17 am
ORD
-
EGE
14h 16m2 stops
$334American Airlines
Wed, Dec 31 - Wed, Jan 7
United Airlines Logo
8:00 am - 12:00 pm
EGE
-
ORD
3h 00mnonstop
United Airlines Logo
9:15 am - 11:25 am
ORD
-
EGE
3h 10mnonstop
$339United Airlines
Fri, Feb 13 - Tue, Feb 17
United Airlines Logo
8:25 am - 12:29 pm
EGE
-
ORD
3h 04mnonstop
United Airlines Logo
4:20 pm - 6:21 pm
ORD
-
EGE
3h 01mnonstop
$360United Airlines
Tue, Dec 30 - Thu, Jan 1
United Airlines Logo
3:30 pm - 11:59 pm
EGE
-
ORD
7h 29m1 stop
United Airlines Logo
8:15 pm - 2:24 pm
ORD
-
EGE
19h 09m2 stops
$364United Airlines
Fri, Feb 13 - Tue, Feb 17
United Airlines Logo
8:25 am - 12:29 pm
EGE
-
ORD
3h 04mnonstop
United Airlines Logo
7:35 am - 2:14 pm
ORD
-
EGE
7h 39m1 stop
$366United Airlines
Tue, Dec 30 - Sat, Jan 3
United Airlines Logo
12:20 pm - 4:15 pm
EGE
-
ORD
2h 55mnonstop
United Airlines Logo
8:45 am - 2:28 pm
ORD
-
EGE
6h 43m1 stop
$370United Airlines
Tue, Dec 30 - Fri, Jan 2

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
Feb 5
EGE12:30 pmVail Eagle County
2h 55m
ORD4:25 pmChicago O'Hare Intl
Feb 9
ORD9:15 amChicago O'Hare Intl
3h 12m
EGE11:27 amVail Eagle County
$291
Find similar
United Airlines
Feb 13
EGE3:30 pmVail Eagle County
7h 29m
1 stop
ORD11:59 pmChicago O'Hare Intl
Feb 17
ORD12:45 pmChicago O'Hare Intl
3h 07m
EGE2:52 pmVail Eagle County
$301
Find similar
United Airlines
Feb 13
EGE3:30 pmVail Eagle County
6h 22m
1 stop
ORD10:52 pmChicago O'Hare Intl
Feb 17
ORD7:10 amChicago O'Hare Intl
6h 23m
1 stop
EGE12:33 pmVail Eagle County
$311
Find similar

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
Dec 31
EGE12:01 pmVail Eagle County
3h 00m
ORD4:01 pmChicago O'Hare Intl
Jan 7
ORD9:01 pmChicago O'Hare Intl
14h 16m
2 stops
EGE10:17 amVail Eagle County
$329
Find similar
American Airlines
Dec 31
EGE3:50 pmVail Eagle County
7h 26m
1 stop
ORD12:16 amChicago O'Hare Intl
Jan 7
ORD9:01 pmChicago O'Hare Intl
14h 16m
2 stops
EGE10:17 amVail Eagle County
$334
Find similar
American Airlines
Dec 30
EGE7:46 amVail Eagle County
8h 31m
1 stop
ORD5:17 pmChicago O'Hare Intl
Jan 2
ORD11:53 amChicago O'Hare Intl
8h 14m
1 stop
EGE7:07 pmVail Eagle County
$380
Find similar

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 December 5, 2025.
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

VailChicago

EGE - ORD

EGEORD

Vail Eagle County

Thu 2/5

12:30 pm-4:25 pm

Nonstop2h 55m

Chicago O'Hare Intl

Mon 2/9

9:15 am-11:27 am

Nonstop3h 12m

$291

VailChicago

EGE - ORD

EGEORD

Vail Eagle County

Fri 2/13

3:30 pm-11:59 pm

1 stop7h 29m

Chicago O'Hare Intl

Tue 2/17

12:45 pm-2:52 pm

Nonstop3h 07m

$301

VailChicago

EGE - ORD

EGEORD

Vail Eagle County

Fri 2/13

3:30 pm-10:52 pm

1 stop6h 22m

Chicago O'Hare Intl

Tue 2/17

7:10 am-12:33 pm

1 stop6h 23m

$311

VailChicago

EGE - ORD

EGEORD

Vail Eagle County

Wed 12/31

12:01 pm-4:01 pm

Nonstop3h 00m

Chicago O'Hare Intl

Wed 1/7

9:01 pm-10:17 am

2 stops14h 16m

$329

VailChicago

EGE - ORD

EGEORD

Vail Eagle County

Wed 12/31

3:50 pm-12:16 am

1 stop7h 26m

Chicago O'Hare Intl

Wed 1/7

9:01 pm-10:17 am

2 stops14h 16m

$334

VailChicago

EGE - ORD

EGEORD

Vail Eagle County

Fri 2/13

8:00 am-12:00 pm

Nonstop3h 00m

Chicago O'Hare Intl

Tue 2/17

9:15 am-11:25 am

Nonstop3h 10m

$339

VailChicago

EGE - ORD

EGEORD

Vail Eagle County

Tue 12/30

8:25 am-12:29 pm

Nonstop3h 04m

Chicago O'Hare Intl

Thu 1/1

4:20 pm-6:21 pm

Nonstop3h 01m

$360

VailChicago

EGE - ORD

EGEORD

Vail Eagle County

Fri 2/13

3:30 pm-11:59 pm

1 stop7h 29m

Chicago O'Hare Intl

Tue 2/17

8:15 pm-2:24 pm

2 stops19h 09m

$364

VailChicago

EGE - ORD

EGEORD

Vail Eagle County

Tue 12/30

8:25 am-12:29 pm

Nonstop3h 04m

Chicago O'Hare Intl

Sat 1/3

7:35 am-2:14 pm

1 stop7h 39m

$366

VailChicago

EGE - ORD

EGEORD

Vail Eagle County

Tue 12/30

12:20 pm-4:15 pm

Nonstop2h 55m

Chicago O'Hare Intl

Fri 1/2

8:45 am-2:28 pm

1 stop6h 43m

$370

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 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 Friday when prices can be found for as low as $331. This is often the case because there is less demand to fly during this day of the week. On the other hand, Sunday 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 $571.

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 evening is the least expensive time of day to depart. momondo users have found prices as low as $208 when looking at flights departing in the evening. Try not to purchase tickets at noon because they tend to be around $686. 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?

No. A direct flight is the cheapest option for a flight between Vail to Chicago O'Hare Intl Airport.

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

As of December 2025, prices for Vail to Chicago O'Hare Intl Airport flights are approximately 18% more expensive when compared to flights at the same time last year.

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

$274

Fastest flight time

2h 55m

Direct flights

Every day
The best one-way flight to Chicago O'Hare Intl Airport from Vail in the past 72 hours is $274. The best round-trip flight deal from Vail to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is $408.
The fastest flight from Vail to Chicago O'Hare Intl Airport takes 2h 55m
Direct flights go from Vail to Chicago O'Hare Intl Airport every day.
Search flight deals

  • 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 50m, 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
9,064 reviews
Search United Airlines flights
American AirlinesPriceFrom $359Free CancellationRating
7.2
11,047 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
South Haven
Schaumburg
Rockford
Merrillville
Gurnee
Naperville
Rosemont
Kenosha
New Buffalo
Joliet
Oak Brook
Orland Park
Racine
Hammond
Tinley Park
Janesville
Aurora
Elgin
Benton Harbor

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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