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Cheap flights from Vail to Chicago from $198

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 12/22. 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

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Vail to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
American Airlines Logo
12:58 pm - 9:09 pm
EGE
-
ORD
7h 11m
1 stop
American Airlines Logo
10:00 pm - 12:03 pm
ORD
-
EGE
15h 03m
2 stops
$410American Airlines
Fri, Oct 2 - Mon, Oct 5
American Airlines Logo
2:12 pm - 11:39 pm
EGE
-
ORD
8h 27m
1 stop
American Airlines Logo
5:00 am - 9:53 am
ORD
-
EGE
5h 53m
1 stop
$415American Airlines
Tue, Jul 28 - Sun, Aug 2
American Airlines Logo
2:12 pm - 11:39 pm
EGE
-
ORD
8h 27m
1 stop
American Airlines Logo
5:00 am - 9:53 am
ORD
-
EGE
5h 53m
1 stop
$452American Airlines
Wed, Jul 15 - Mon, Jul 27
American Airlines Logo
2:12 pm - 11:39 pm
EGE
-
ORD
8h 27m
1 stop
American Airlines Logo
1:25 pm - 6:50 pm
ORD
-
EGE
6h 25m
1 stop
$463American Airlines
Tue, Jul 28 - Fri, Jul 31
United Airlines Logo
8:00 am - 11:52 am
EGE
-
ORD
2h 52mnonstop
United Airlines Logo
4:00 pm - 6:04 pm
ORD
-
EGE
3h 04mnonstop
$469United Airlines
Sat, Jul 18 - Sat, Jul 25
United Airlines Logo
8:00 am - 11:52 am
EGE
-
ORD
2h 52mnonstop
United Airlines Logo
4:00 pm - 6:04 pm
ORD
-
EGE
3h 04mnonstop
$474United Airlines
Sat, Aug 1 - Sat, Aug 8
United Airlines Logo
8:00 am - 11:52 am
EGE
-
ORD
2h 52mnonstop
United Airlines Logo
6:59 am - 12:03 pm
ORD
-
EGE
6h 04m
1 stop
$479United Airlines
Sat, Jul 18 - Sat, Jul 25
United Airlines Logo
8:00 am - 11:52 am
EGE
-
ORD
2h 52mnonstop
United Airlines Logo
2:33 pm - 8:30 pm
ORD
-
EGE
6h 57m
1 stop
$483United Airlines
Sat, Aug 1 - Sat, Aug 8
American Airlines Logo
2:12 pm - 10:15 pm
EGE
-
ORD
7h 03m
1 stop
American Airlines Logo
12:05 pm - 6:50 pm
ORD
-
EGE
7h 45m
1 stop
$489American Airlines
Wed, Jul 15 - Sat, Jul 18
United Airlines Logo
3:31 pm - 9:18 pm
EGE
-
ORD
4h 47m
1 stop
United Airlines Logo
7:00 am - 12:42 pm
ORD
-
EGE
6h 42m
1 stop
$492United Airlines
Sat, Oct 10 - Mon, Oct 12

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American Airlines flights from Vail to Chicago

Our best American Airlines deals on Vail to Chicago flight tickets
American Airlines
Oct 2
EGE12:58 pmVail Eagle County
7h 11m
1 stop
ORD9:09 pmChicago O'Hare Intl
Oct 5
ORD10:00 pmChicago O'Hare Intl
15h 03m
2 stops
EGE12:03 pmVail Eagle County
$410
American Airlines
Jul 28
EGE2:12 pmVail Eagle County
8h 27m
1 stop
ORD11:39 pmChicago O'Hare Intl
Aug 2
ORD5:00 amChicago O'Hare Intl
5h 53m
1 stop
EGE9:53 amVail Eagle County
$415
American Airlines
Jul 15
EGE2:12 pmVail Eagle County
8h 27m
1 stop
ORD11:39 pmChicago O'Hare Intl
Jul 27
ORD5:00 amChicago O'Hare Intl
5h 53m
1 stop
EGE9:53 amVail Eagle County
$452

United Airlines flights from Vail to Chicago

Our best United Airlines deals on Vail to Chicago flight tickets
United Airlines
Aug 25
EGE3:29 pmVail Eagle County
5h 23m
1 stop
ORD9:52 pmChicago O'Hare Intl
Aug 29
ORD4:00 pmChicago O'Hare Intl
3h 02m
EGE6:02 pmVail Eagle County
$462
United Airlines
Jul 18
EGE8:00 amVail Eagle County
2h 52m
ORD11:52 amChicago O'Hare Intl
Jul 25
ORD4:00 pmChicago O'Hare Intl
3h 04m
EGE6:04 pmVail Eagle County
$469
United Airlines
Aug 1
EGE8:00 amVail Eagle County
2h 52m
ORD11:52 amChicago O'Hare Intl
Aug 8
ORD4:00 pmChicago O'Hare Intl
3h 04m
EGE6:04 pmVail Eagle County
$474

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 June 26, 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

Fri 10/2

12:58 pm-9:09 pm

1 stop7h 11m

Chicago O'Hare Intl

Mon 10/5

10:00 pm-12:03 pm

2 stops15h 03m

$410

VailChicago

EGE - ORD

EGEORD

Vail Eagle County

Tue 7/28

2:12 pm-11:39 pm

1 stop8h 27m

Chicago O'Hare Intl

Sun 8/2

5:00 am-9:53 am

1 stop5h 53m

$415

VailChicago

EGE - ORD

EGEORD

Vail Eagle County

Wed 7/15

2:12 pm-11:39 pm

1 stop8h 27m

Chicago O'Hare Intl

Mon 7/27

5:00 am-9:53 am

1 stop5h 53m

$452

VailChicago

EGE - ORD

EGEORD

Vail Eagle County

Tue 7/28

2:12 pm-11:39 pm

1 stop8h 27m

Chicago O'Hare Intl

Fri 7/31

1:25 pm-6:50 pm

1 stop6h 25m

$463
Quickest round-trip

VailChicago

EGE - ORD

EGEORD

Vail Eagle County

Sat 7/18

8:00 am-11:52 am

Nonstop2h 52m

Chicago O'Hare Intl

Sat 7/25

4:00 pm-6:04 pm

Nonstop3h 04m

$469

VailChicago

EGE - ORD

EGEORD

Vail Eagle County

Sat 8/1

8:00 am-11:52 am

Nonstop2h 52m

Chicago O'Hare Intl

Sat 8/8

4:00 pm-6:04 pm

Nonstop3h 04m

$474

VailChicago

EGE - ORD

EGEORD

Vail Eagle County

Sat 7/18

8:00 am-11:52 am

Nonstop2h 52m

Chicago O'Hare Intl

Sat 7/25

6:59 am-12:03 pm

1 stop6h 04m

$479

VailChicago

EGE - ORD

EGEORD

Vail Eagle County

Sat 8/1

8:00 am-11:52 am

Nonstop2h 52m

Chicago O'Hare Intl

Sat 8/8

2:33 pm-8:30 pm

1 stop6h 57m

$483

VailChicago

EGE - ORD

EGEORD

Vail Eagle County

Wed 7/15

2:12 pm-10:15 pm

1 stop7h 03m

Chicago O'Hare Intl

Sat 7/18

12:05 pm-6:50 pm

1 stop7h 45m

$489

VailChicago

EGE - ORD

EGEORD

Vail Eagle County

Sat 10/10

3:31 pm-9:18 pm

1 stop4h 47m

Chicago O'Hare Intl

Mon 10/12

7:00 am-12:42 pm

1 stop6h 42m

$492

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 month to fly to Chicago?

The month of October is, on average, the cheapest month to fly to Chicago from Vail, with most prices found around $0. If you’re not able to fly to Chicago in October, then February is your next best option. Flight prices from Vail to Chicago during February average around $191.

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 $310. 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 $511.

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 $239. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $533.

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 to Chicago flights?

There are 4 cabin classes available to choose from on Vail 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 23% 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

$336

Fastest flight time

2h 52m

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 $336. The best round-trip flight deal from Vail to Chicago found on momondo in the last 72 hours is $459.
The fastest flight from Vail to Chicago takes 2h 52m
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

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 52m.

  • 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
9,893 reviews
Search United Airlines flights
American AirlinesPriceFrom $265Free CancellationRating
7.1
11,768 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
Portage
Benton Harbor
Saint Joseph
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