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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 4/21. 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

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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
3:25 pm - 9:54 pm
EGE
-
ORD
5h 29m
1 stop
United Airlines Logo
4:00 pm - 6:05 pm
ORD
-
EGE
3h 05mnonstop
$389United Airlines
火, 6月 16 - 土, 6月 27
United Airlines Logo
1:38 pm - 9:20 pm
EGE
-
ORD
6h 42m
1 stop
United Airlines Logo
7:00 am - 12:28 pm
ORD
-
EGE
6h 28m
1 stop
$399United Airlines
木, 4月 9 - 日, 4月 12
United Airlines Logo
3:15 pm - 11:28 pm
EGE
-
ORD
7h 13m
1 stop
United Airlines Logo
2:35 pm - 8:25 pm
ORD
-
EGE
6h 50m
1 stop
$420United Airlines
木, 4月 9 - 月, 4月 13
American Airlines Logo
8:00 am - 5:44 pm
EGE
-
ORD
8h 44m
1 stop
American Airlines Logo
12:30 pm - 7:09 pm
ORD
-
EGE
7h 39m
1 stop
$439American Airlines
月, 4月 20 - 月, 4月 27
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
$445American Airlines
木, 5月 14 - 月, 5月 18
American Airlines Logo
10:35 am - 7:43 pm
EGE
-
ORD
8h 08m
1 stop
American Airlines Logo
8:19 am - 1:32 pm
ORD
-
EGE
6h 13m
1 stop
$474American Airlines
木, 7月 2 - 日, 7月 5
American Airlines Logo
2:14 pm - 12:06 am
EGE
-
ORD
8h 52m
1 stop
American Airlines Logo
5:00 am - 9:54 am
ORD
-
EGE
5h 54m
1 stop
$475American Airlines
木, 8月 13 - 火, 8月 18
American Airlines Logo
8:00 am - 8:05 pm
EGE
-
ORD
11h 05m
2 stops
American Airlines Logo
12:30 pm - 7:09 pm
ORD
-
EGE
7h 39m
1 stop
$488American Airlines
火, 5月 12 - 火, 5月 19
United Airlines Logo
1:38 pm - 9:20 pm
EGE
-
ORD
6h 42m
1 stop
United Airlines Logo
7:00 am - 12:28 pm
ORD
-
EGE
6h 28m
1 stop
$489United Airlines
水, 4月 8 - 日, 4月 12
American Airlines Logo
2:12 pm - 11:31 pm
EGE
-
ORD
8h 19m
1 stop
American Airlines Logo
6:04 am - 1:32 pm
ORD
-
EGE
8h 28m
1 stop
$490American Airlines
木, 7月 30 - 日, 8月 2

United Airlines flights from Vail to Chicago

Our best United Airlines deals on Vail to Chicago flight tickets
United Airlines
Jun 16
EGE3:25 pmVail Eagle County
5h 29m
1 stop
ORD9:54 pmChicago O'Hare Intl
Jun 27
ORD4:00 pmChicago O'Hare Intl
3h 05m
EGE6:05 pmVail Eagle County
$389
United Airlines
Apr 9
EGE1:38 pmVail Eagle County
6h 42m
1 stop
ORD9:20 pmChicago O'Hare Intl
Apr 12
ORD7:00 amChicago O'Hare Intl
6h 28m
1 stop
EGE12:28 pmVail Eagle County
$399
United Airlines
Apr 9
EGE3:15 pmVail Eagle County
7h 13m
1 stop
ORD11:28 pmChicago O'Hare Intl
Apr 13
ORD2:35 pmChicago O'Hare Intl
6h 50m
1 stop
EGE8:25 pmVail Eagle County
$420

Alaska Airlines flights from Vail to Chicago

Our best Alaska Airlines deals on Vail to Chicago flight tickets
Alaska Airlines
Mar 30
EGE1:15 pmVail Eagle County
24h 59m
3 stops
ORD3:14 pmChicago O'Hare Intl
Apr 3
ORD2:09 pmChicago O'Hare Intl
23h 25m
2 stops
EGE12:34 pmVail Eagle County
$1,233
Alaska Airlines
Mar 30
EGE1:15 pmVail Eagle County
22h 58m
3 stops
ORD1:13 pmChicago O'Hare Intl
Apr 3
ORD3:22 pmChicago O'Hare Intl
22h 12m
3 stops
EGE12:34 pmVail Eagle County
$1,245
Alaska Airlines
Apr 2
EGE1:15 pmVail Eagle County
22h 58m
3 stops
ORD1:13 pmChicago O'Hare Intl
Apr 5
ORD2:09 pmChicago O'Hare Intl
23h 25m
3 stops
EGE12:34 pmVail Eagle County
$1,411

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 3月 27, 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

Cheapest round-trip
Quickest round-trip

VailChicago

EGE - ORD

EGEORD

Vail Eagle County

火 6/16

3:25 pm-9:54 pm

1 stop5h 29m

Chicago O'Hare Intl

土 6/27

4:00 pm-6:05 pm

Nonstop3h 05m

$389

VailChicago

EGE - ORD

EGEORD

Vail Eagle County

木 4/9

1:38 pm-9:20 pm

1 stop6h 42m

Chicago O'Hare Intl

日 4/12

7:00 am-12:28 pm

1 stop6h 28m

$399

VailChicago

EGE - ORD

EGEORD

Vail Eagle County

木 4/9

3:15 pm-11:28 pm

1 stop7h 13m

Chicago O'Hare Intl

月 4/13

2:35 pm-8:25 pm

1 stop6h 50m

$420

VailChicago

EGE - ORD

EGEORD

Vail Eagle County

月 4/20

8:00 am-5:44 pm

1 stop8h 44m

Chicago O'Hare Intl

月 4/27

12:30 pm-7:09 pm

1 stop7h 39m

$439

VailChicago

EGE - ORD

EGEORD

Vail Eagle County

木 5/14

8:00 am-5:44 pm

1 stop8h 44m

Chicago O'Hare Intl

月 5/18

11:43 am-7:09 pm

1 stop8h 26m

$445

VailChicago

EGE - ORD

EGEORD

Vail Eagle County

木 7/2

10:35 am-7:43 pm

1 stop8h 08m

Chicago O'Hare Intl

日 7/5

8:19 am-1:32 pm

1 stop6h 13m

$474

VailChicago

EGE - ORD

EGEORD

Vail Eagle County

木 8/13

2:14 pm-12:06 am

1 stop8h 52m

Chicago O'Hare Intl

火 8/18

5:00 am-9:54 am

1 stop5h 54m

$475

VailChicago

EGE - ORD

EGEORD

Vail Eagle County

火 5/12

8:00 am-8:05 pm

2 stops11h 05m

Chicago O'Hare Intl

火 5/19

12:30 pm-7:09 pm

1 stop7h 39m

$488

VailChicago

EGE - ORD

EGEORD

Vail Eagle County

水 4/8

1:38 pm-9:20 pm

1 stop6h 42m

Chicago O'Hare Intl

日 4/12

7:00 am-12:28 pm

1 stop6h 28m

$489

VailChicago

EGE - ORD

EGEORD

Vail Eagle County

木 7/30

2:12 pm-11:31 pm

1 stop8h 19m

Chicago O'Hare Intl

日 8/2

6:04 am-1:32 pm

1 stop8h 28m

$490

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 Sunday when prices can be found for as low as $299. This is often the case because there is less demand to fly during this day of the week. When flying out on a Wednesday, the most expensive travel day of the week, you can expect to see flight prices from Vail to Chicago for around $654.

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 morning. Flights from Vail to Chicago during this time can be as low as $483. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $735.

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 40% 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

$268

Fastest flight time

2h 58m

Direct flights

Mon, Thu, Fri and Sun

Airports in Chicago

3 airports
The best one-way flight to Chicago from Vail in the past 72 hours is $268. The best round-trip flight deal from Vail to Chicago found on momondo in the last 72 hours is $397.
The fastest flight from Vail to Chicago takes 2h 58m
Direct flights go from Vail to Chicago on Monday, Thursday, Friday 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 58m.

  • 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
9,491 reviews
Search United Airlines flights
American AirlinesPriceFrom $265Free CancellationRating
7.1
11,506 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 3 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 $265, 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 14 flights out of Vail into Chicago in an average week, so prices vary by time and availability. 11,520 American Airlines reviews by users on momondo have scored the airline at 7.1/10.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Saint Joseph
Benton Harbor
Portage
Lansing
Valparaiso
Schererville
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