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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 7/1. 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
2:12 pm - 11:39 pm
EGE
-
ORD
8h 27m
1 stop
American Airlines Logo
7:00 am - 1:32 pm
ORD
-
EGE
7h 32m
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
5:59 am - 1:31 pm
ORD
-
EGE
8h 32m
1 stop
$442American Airlines
Fri, Jun 26 - Tue, Jun 30
American Airlines Logo
2:12 pm - 11:32 pm
EGE
-
ORD
8h 20m
1 stop
American Airlines Logo
1:25 pm - 7:04 pm
ORD
-
EGE
6h 39m
1 stop
$447American Airlines
Thu, Jun 11 - Wed, Jun 17
United Airlines Logo
8:00 am - 11:55 am
EGE
-
ORD
2h 55mnonstop
United Airlines Logo
4:00 pm - 6:05 pm
ORD
-
EGE
3h 05mnonstop
$459United Airlines
Sat, Jun 6 - Fri, Jun 12
American Airlines Logo
10:33 am - 8:11 pm
EGE
-
ORD
8h 38m
1 stop
American Airlines Logo
5:00 am - 9:53 am
ORD
-
EGE
5h 53m
1 stop
$463American Airlines
Thu, Jun 18 - Tue, Jun 23
American Airlines Logo
2:12 pm - 11:32 pm
EGE
-
ORD
8h 20m
1 stop
American Airlines Logo
11:43 am - 7:04 pm
ORD
-
EGE
8h 21m
1 stop
$464American Airlines
Thu, Jun 11 - Mon, Jun 15
United Airlines Logo
7:05 am - 1:15 pm
EGE
-
ORD
5h 10m
1 stop
United Airlines Logo
4:00 pm - 6:05 pm
ORD
-
EGE
3h 05mnonstop
$469United Airlines
Sat, Jun 6 - Fri, Jun 12
American Airlines Logo
2:12 pm - 9:15 pm
EGE
-
ORD
6h 03m
1 stop
American Airlines Logo
1:29 pm - 7:04 pm
ORD
-
EGE
6h 35m
1 stop
$479American Airlines
Sat, May 30 - Tue, Jun 2
American Airlines Logo
1:12 pm - 11:12 pm
EGE
-
ORD
9h 00m
1 stop
American Airlines Logo
10:00 pm - 12:03 pm
ORD
-
EGE
15h 03m
2 stops
$483American Airlines
Thu, Oct 1 - Fri, Oct 16
American Airlines Logo
2:12 pm - 10:10 pm
EGE
-
ORD
6h 58m
1 stop
American Airlines Logo
6:00 am - 1:31 pm
ORD
-
EGE
8h 31m
1 stop
$489American Airlines
Fri, May 29 - Mon, Jun 1

American Airlines flights from Vail to Chicago

Our best American Airlines deals on Vail to Chicago flight tickets
American Airlines
Jul 29
EGE2:12 pmVail Eagle County
8h 27m
1 stop
ORD11:39 pmChicago O'Hare Intl
Aug 4
ORD7:00 amChicago O'Hare Intl
7h 32m
1 stop
EGE1:32 pmVail Eagle County
$415
American Airlines
Jun 26
EGE2:12 pmVail Eagle County
8h 20m
1 stop
ORD11:32 pmChicago O'Hare Intl
Jun 30
ORD5:59 amChicago O'Hare Intl
8h 32m
1 stop
EGE1:31 pmVail Eagle County
$442
American Airlines
Jun 11
EGE2:12 pmVail Eagle County
8h 20m
1 stop
ORD11:32 pmChicago O'Hare Intl
Jun 17
ORD1:25 pmChicago O'Hare Intl
6h 39m
1 stop
EGE7:04 pmVail Eagle County
$447

United Airlines flights from Vail to Chicago

Our best United Airlines deals on Vail to Chicago flight tickets
United Airlines
Jun 6
EGE8:00 amVail Eagle County
2h 55m
ORD11:55 amChicago O'Hare Intl
Jun 12
ORD4:00 pmChicago O'Hare Intl
3h 05m
EGE6:05 pmVail Eagle County
$459
United Airlines
Jun 6
EGE7:05 amVail Eagle County
5h 10m
1 stop
ORD1:15 pmChicago O'Hare Intl
Jun 12
ORD4:00 pmChicago O'Hare Intl
3h 05m
EGE6:05 pmVail Eagle County
$469
United Airlines
Jul 25
EGE8:00 amVail Eagle County
2h 55m
ORD11:55 amChicago O'Hare Intl
Aug 4
ORD7:05 amChicago O'Hare Intl
5h 58m
1 stop
EGE12:03 pmVail Eagle County
$496

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 May 12, 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

VailChicago

EGE - ORD

EGEORD

Vail Eagle County

Wed 7/29

2:12 pm-11:39 pm

1 stop8h 27m

Chicago O'Hare Intl

Tue 8/4

7:00 am-1:32 pm

1 stop7h 32m

$415

VailChicago

EGE - ORD

EGEORD

Vail Eagle County

Fri 6/26

2:12 pm-11:32 pm

1 stop8h 20m

Chicago O'Hare Intl

Tue 6/30

5:59 am-1:31 pm

1 stop8h 32m

$442

VailChicago

EGE - ORD

EGEORD

Vail Eagle County

Thu 6/11

2:12 pm-11:32 pm

1 stop8h 20m

Chicago O'Hare Intl

Wed 6/17

1:25 pm-7:04 pm

1 stop6h 39m

$447
Quickest round-trip

VailChicago

EGE - ORD

EGEORD

Vail Eagle County

Sat 6/6

8:00 am-11:55 am

Nonstop2h 55m

Chicago O'Hare Intl

Fri 6/12

4:00 pm-6:05 pm

Nonstop3h 05m

$459

VailChicago

EGE - ORD

EGEORD

Vail Eagle County

Thu 6/18

10:33 am-8:11 pm

1 stop8h 38m

Chicago O'Hare Intl

Tue 6/23

5:00 am-9:53 am

1 stop5h 53m

$463

VailChicago

EGE - ORD

EGEORD

Vail Eagle County

Thu 6/11

2:12 pm-11:32 pm

1 stop8h 20m

Chicago O'Hare Intl

Mon 6/15

11:43 am-7:04 pm

1 stop8h 21m

$464

VailChicago

EGE - ORD

EGEORD

Vail Eagle County

Sat 6/6

7:05 am-1:15 pm

1 stop5h 10m

Chicago O'Hare Intl

Fri 6/12

4:00 pm-6:05 pm

Nonstop3h 05m

$469

VailChicago

EGE - ORD

EGEORD

Vail Eagle County

Sat 5/30

2:12 pm-9:15 pm

1 stop6h 03m

Chicago O'Hare Intl

Tue 6/2

1:29 pm-7:04 pm

1 stop6h 35m

$479

VailChicago

EGE - ORD

EGEORD

Vail Eagle County

Thu 10/1

1:12 pm-11:12 pm

1 stop9h 00m

Chicago O'Hare Intl

Fri 10/16

10:00 pm-12:03 pm

2 stops15h 03m

$483

VailChicago

EGE - ORD

EGEORD

Vail Eagle County

Fri 5/29

2:12 pm-10:10 pm

1 stop6h 58m

Chicago O'Hare Intl

Mon 6/1

6:00 am-1:31 pm

1 stop8h 31m

$489

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 typical price of a round-trip flight between Vail and Chicago?

What is the cheapest month to fly to Chicago?

The month of February is, on average, the cheapest month to fly to Chicago from Vail, with most prices found around $191. If you’re not able to fly to Chicago in February, then October is your next best option. Flight prices from Vail to Chicago during October average around $248.

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 $418. This is often the case because there is less demand to fly during this day of the week. When flying out on a Saturday, the most expensive travel day of the week, you can expect to see flight prices from Vail to Chicago for around $603.

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 $484. 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

Can stopping save me money on Vail to Chicago flights?

You could potentially save up to 28% 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

$560

Fastest flight time

2h 55m

Direct flights

Mon and Sun

Airports in Chicago

3 airports
The best flight deal from Vail to Chicago found on momondo in the last 72 hours is $560
The fastest flight from Vail to Chicago takes 2h 55m
Direct flights go from Vail to Chicago on Monday 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

Frequently asked questions about flying from Vail to Chicago

  • 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 55m.

  • 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
9,701 reviews
Search United Airlines flights
American AirlinesPriceFrom $331Free CancellationRating
7.1
11,661 reviews
Search American Airlines flights

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
Munster
Schererville
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