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Cheap flights from Vail to Chicago from $221

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 1/16. 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

United Airlines Logo
3:20 pm - 11:59 pmEGE-ORD
7h 39m1 stop
United Airlines Logo
7:10 am - 12:28 pmORD-EGE
6h 18m1 stop
$299United Airlines
Find Deal
Fri, Sep 26 - Sat, Sep 27
United Airlines Logo
1:40 pm - 8:25 pmEGE-ORD
5h 45m1 stop
United Airlines Logo
2:53 pm - 8:08 pmORD-EGE
6h 15m1 stop
$317United Airlines
Find Deal
Tue, Oct 14 - Sat, Oct 18
United Airlines Logo
3:21 pm - 11:59 pmEGE-ORD
7h 38m1 stop
United Airlines Logo
8:51 am - 10:59 amORD-EGE
3h 08mnonstop
$339United Airlines
Find Deal
Fri, Feb 27 - Mon, Mar 2
United Airlines Logo
3:21 pm - 10:52 pmEGE-ORD
6h 31m1 stop
United Airlines Logo
7:35 am - 2:17 pmORD-EGE
7h 42m1 stop
$344United Airlines
Find Deal
Fri, Feb 27 - Mon, Mar 2
American Airlines Logo
8:00 am - 3:28 pmEGE-ORD
6h 28m1 stop
American Airlines Logo
11:46 am - 7:11 pmORD-EGE
8h 25m1 stop
$349American Airlines
Find Deal
Thu, Nov 13 - Sun, Nov 16
United Airlines Logo
1:30 pm - 8:25 pmEGE-ORD
5h 55m1 stop
United Airlines Logo
7:10 am - 12:38 pmORD-EGE
6h 28m1 stop
$364United Airlines
Find Deal
Sat, Oct 18 - Mon, Oct 20
American Airlines Logo
10:34 am - 2:34 pmEGE-ORD
3h 00mnonstop
American Airlines Logo
10:45 am - 12:51 pmORD-EGE
3h 06mnonstop
$369American Airlines
Find Deal
Fri, Feb 27 - Mon, Mar 2
United Airlines Logo
3:20 pm - 11:59 pmEGE-ORD
7h 39m1 stop
United Airlines Logo
2:53 pm - 8:08 pmORD-EGE
6h 15m1 stop
$374United Airlines
Find Deal
Mon, Oct 13 - Sat, Oct 18
American Airlines Logo
8:00 am - 5:17 pmEGE-ORD
8h 17m1 stop
American Airlines Logo
1:23 pm - 7:11 pmORD-EGE
6h 48m1 stop
$400American Airlines
Find Deal
Fri, Nov 14 - Sun, Nov 16
Delta Logo
2:56 pm - 9:46 pmEGE-MDW
5h 50m1 stop
Delta Logo
6:00 am - 1:55 pmMDW-EGE
8h 55m1 stop
$619Delta
Find Deal
Thu, Mar 5 - Mon, Mar 9

American Airlines flights from Vail to Chicago

Our best American Airlines deals on Vail to Chicago flight tickets
American Airlines
Nov 13
EGE8:00 amVail Eagle County
6h 28m
1 stop
ORD3:28 pmChicago O'Hare Intl
Nov 16
ORD11:46 amChicago O'Hare Intl
8h 25m
1 stop
EGE7:11 pmVail Eagle County
$349
Find similar
American Airlines
Feb 27
EGE10:34 amVail Eagle County
3h 00m
ORD2:34 pmChicago O'Hare Intl
Mar 2
ORD10:45 amChicago O'Hare Intl
3h 06m
EGE12:51 pmVail Eagle County
$369
Find similar
American Airlines
Nov 14
EGE8:00 amVail Eagle County
8h 17m
1 stop
ORD5:17 pmChicago O'Hare Intl
Nov 16
ORD1:23 pmChicago O'Hare Intl
6h 48m
1 stop
EGE7:11 pmVail Eagle County
$400
Find similar

United Airlines flights from Vail to Chicago

Our best United Airlines deals on Vail to Chicago flight tickets
United Airlines
Sep 26
EGE3:20 pmVail Eagle County
7h 39m
1 stop
ORD11:59 pmChicago O'Hare Intl
Sep 27
ORD7:10 amChicago O'Hare Intl
6h 18m
1 stop
EGE12:28 pmVail Eagle County
$299
Find similar
United Airlines
Oct 14
EGE1:40 pmVail Eagle County
5h 45m
1 stop
ORD8:25 pmChicago O'Hare Intl
Oct 18
ORD2:53 pmChicago O'Hare Intl
6h 15m
1 stop
EGE8:08 pmVail Eagle County
$317
Find similar
United Airlines
Feb 27
EGE3:21 pmVail Eagle County
7h 38m
1 stop
ORD11:59 pmChicago O'Hare Intl
Mar 2
ORD8:51 amChicago O'Hare Intl
3h 08m
EGE10:59 amVail Eagle County
$339
Find similar

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 September 15, 2025.
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 9/26

3:20 pm-11:59 pm

1 stop7h 39m

Chicago O'Hare Intl

Sat 9/27

7:10 am-12:28 pm

1 stop6h 18m

$299

VailChicago

EGE - ORD

EGEORD

Vail Eagle County

Tue 10/14

1:40 pm-8:25 pm

1 stop5h 45m

Chicago O'Hare Intl

Sat 10/18

2:53 pm-8:08 pm

1 stop6h 15m

$317

VailChicago

EGE - ORD

EGEORD

Vail Eagle County

Fri 2/27

3:21 pm-11:59 pm

1 stop7h 38m

Chicago O'Hare Intl

Mon 3/2

8:51 am-10:59 am

Nonstop3h 08m

$339

VailChicago

EGE - ORD

EGEORD

Vail Eagle County

Fri 2/27

3:21 pm-10:52 pm

1 stop6h 31m

Chicago O'Hare Intl

Mon 3/2

7:35 am-2:17 pm

1 stop7h 42m

$344

VailChicago

EGE - ORD

EGEORD

Vail Eagle County

Thu 11/13

8:00 am-3:28 pm

1 stop6h 28m

Chicago O'Hare Intl

Sun 11/16

11:46 am-7:11 pm

1 stop8h 25m

$349

VailChicago

EGE - ORD

EGEORD

Vail Eagle County

Sat 10/18

1:30 pm-8:25 pm

1 stop5h 55m

Chicago O'Hare Intl

Mon 10/20

7:10 am-12:38 pm

1 stop6h 28m

$364

VailChicago

EGE - ORD

EGEORD

Vail Eagle County

Fri 2/27

10:34 am-2:34 pm

Nonstop3h 00m

Chicago O'Hare Intl

Mon 3/2

10:45 am-12:51 pm

Nonstop3h 06m

$369

VailChicago

EGE - ORD

EGEORD

Vail Eagle County

Mon 10/13

3:20 pm-11:59 pm

1 stop7h 39m

Chicago O'Hare Intl

Sat 10/18

2:53 pm-8:08 pm

1 stop6h 15m

$374

VailChicago

EGE - ORD

EGEORD

Vail Eagle County

Fri 11/14

8:00 am-5:17 pm

1 stop8h 17m

Chicago O'Hare Intl

Sun 11/16

1:23 pm-7:11 pm

1 stop6h 48m

$400

VailChicago

EGE - MDW

EGEMDW

Vail Eagle County

Thu 3/5

2:56 pm-9:46 pm

1 stop5h 50m

Chicago Midway

Mon 3/9

6:00 am-1:55 pm

1 stop8h 55m

$619

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 Friday 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 $501.

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 $192. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $622.

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?

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

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

$210

Fastest flight time

2h 38m

Direct flights

Mon, Tue, Thu, Fri, Sat and Sun

Airports in Chicago

1 airport
The best one-way flight to Chicago from Vail in the past 72 hours is $210. The best round-trip flight deal from Vail to Chicago found on momondo in the last 72 hours is $343.
The fastest flight from Vail to Chicago takes 2h 38m
Direct flights go from Vail to Chicago on Monday, Tuesday, Thursday, Friday, Saturday and Sunday. There are no airlines offering direct flights.
There is 1 airport near Chicago: 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 38m.

  • 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 $329Free CancellationRating
7.4
8,929 reviews
Search United Airlines flights
American AirlinesPriceFrom $359Free CancellationRating
7.2
10,000 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 2 flights/week on average for this route. A good United Airlines flight deal for Vail to Chicago starts from $329 round-trip, up to an average price of $519. Our users have rated United Airlines at 7.4/10.

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
Lansing
Portage
Schererville
Valparaiso
Crown Point
Munster
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