Latest deals
Insights
When to book
FAQs
Reviews
Price Alerts

Cheap flights from Vail to Chicago from $146

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 3/20. 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

Discover deals from 900+ travel sites with momondo.

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

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
4:20 pm - 6:21 pm
ORD
-
EGE
3h 01mnonstop
$331United Airlines
Fri, Jan 30 - Sun, Feb 1
United Airlines Logo
1:22 pm - 6:46 pm
EGE
-
ORD
4h 24m1 stop
United Airlines Logo
4:20 pm - 6:21 pm
ORD
-
EGE
3h 01mnonstop
$341United Airlines
Fri, Jan 30 - Sun, Feb 1
Delta Logo
3:10 pm - 10:07 pm
EGE
-
MDW
5h 57m1 stop
Delta Logo
6:00 am - 2:05 pm
MDW
-
EGE
9h 05m1 stop
$351Delta
Tue, Jan 13 - Tue, Jan 27
United Airlines Logo
1:22 pm - 6:46 pm
EGE
-
ORD
4h 24m1 stop
United Airlines Logo
8:45 am - 2:28 pm
ORD
-
EGE
6h 43m1 stop
$351United Airlines
Fri, Jan 30 - Sun, Feb 1
American Airlines Logo
12:13 pm - 11:44 pm
EGE
-
ORD
10h 31m2 stops
American Airlines Logo
8:10 am - 2:10 pm
ORD
-
EGE
7h 00m1 stop
$356American Airlines
Tue, Jan 13 - Tue, Jan 27
American Airlines Logo
10:57 am - 2:47 pm
EGE
-
ORD
2h 50mnonstop
American Airlines Logo
8:24 am - 10:31 am
ORD
-
EGE
3h 07mnonstop
$381American Airlines
Thu, Jan 8 - Sun, Jan 11
American Airlines Logo
12:13 pm - 9:07 pm
EGE
-
ORD
7h 54m1 stop
American Airlines Logo
8:24 am - 10:31 am
ORD
-
EGE
3h 07mnonstop
$391American Airlines
Thu, Jan 8 - Sun, Jan 11
Delta Logo
3:10 pm - 11:59 pm
EGE
-
ORD
7h 49m1 stop
Delta Logo
5:30 am - 2:05 pm
ORD
-
EGE
9h 35m1 stop
$401Delta
Thu, Jan 8 - Sun, Jan 11
United Airlines Logo
8:00 am - 12:00 pm
EGE
-
ORD
3h 00mnonstop
United Airlines Logo
12:45 pm - 2:52 pm
ORD
-
EGE
3h 07mnonstop
$440United Airlines
Sat, Feb 14 - Tue, Feb 17
Alaska Airlines Logo
2:39 pm - 11:59 pm
EGE
-
ORD
8h 20m1 stop
Alaska Airlines Logo
3:07 pm - 4:56 pm
ORD
-
EGE
26h 49m1 stop
$443Alaska Airlines
Sat, Feb 14 - Tue, Feb 17

United Airlines flights from Vail to Chicago

Our best United Airlines deals on Vail to Chicago flight tickets
United Airlines
Jan 30
EGE12:30 pmVail Eagle County
2h 55m
ORD4:25 pmChicago O'Hare Intl
Feb 1
ORD4:20 pmChicago O'Hare Intl
3h 01m
EGE6:21 pmVail Eagle County
$331
Find similar
United Airlines
Jan 30
EGE12:30 pmVail Eagle County
2h 55m
ORD4:25 pmChicago O'Hare Intl
Feb 2
ORD10:40 amChicago O'Hare Intl
4h 48m
1 stop
EGE2:28 pmVail Eagle County
$341
Find similar
United Airlines
Jan 30
EGE1:22 pmVail Eagle County
4h 24m
1 stop
ORD6:46 pmChicago O'Hare Intl
Feb 1
ORD8:45 amChicago O'Hare Intl
6h 43m
1 stop
EGE2:28 pmVail Eagle County
$351
Find similar

American Airlines flights from Vail to Chicago

Our best American Airlines deals on Vail to Chicago flight tickets
American Airlines
Jan 13
EGE12:13 pmVail Eagle County
10h 31m
2 stops
ORD11:44 pmChicago O'Hare Intl
Jan 27
ORD8:10 amChicago O'Hare Intl
7h 00m
1 stop
EGE2:10 pmVail Eagle County
$356
Find similar
American Airlines
Feb 24
EGE2:35 pmVail Eagle County
6h 48m
1 stop
ORD10:23 pmChicago O'Hare Intl
Feb 26
ORD8:05 amChicago O'Hare Intl
3h 04m
EGE10:09 amVail Eagle County
$396
Find similar
American Airlines
Feb 24
EGE2:35 pmVail Eagle County
6h 48m
1 stop
ORD10:23 pmChicago O'Hare Intl
Feb 26
ORD5:00 amChicago O'Hare Intl
8h 03m
1 stop
EGE12:03 pmVail Eagle County
$406
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 December 23, 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 1/30

12:30 pm-4:25 pm

Nonstop2h 55m

Chicago O'Hare Intl

Sun 2/1

4:20 pm-6:21 pm

Nonstop3h 01m

$331

VailChicago

EGE - ORD

EGEORD

Vail Eagle County

Fri 1/30

1:22 pm-6:46 pm

1 stop4h 24m

Chicago O'Hare Intl

Sun 2/1

4:20 pm-6:21 pm

Nonstop3h 01m

$341

VailChicago

EGE - MDW

EGEMDW

Vail Eagle County

Tue 1/13

3:10 pm-10:07 pm

1 stop5h 57m

Chicago Midway

Tue 1/27

6:00 am-2:05 pm

1 stop9h 05m

$351

VailChicago

EGE - ORD

EGEORD

Vail Eagle County

Fri 1/30

1:22 pm-6:46 pm

1 stop4h 24m

Chicago O'Hare Intl

Sun 2/1

8:45 am-2:28 pm

1 stop6h 43m

$351

VailChicago

EGE - ORD

EGEORD

Vail Eagle County

Tue 1/13

12:13 pm-11:44 pm

2 stops10h 31m

Chicago O'Hare Intl

Tue 1/27

8:10 am-2:10 pm

1 stop7h 00m

$356

VailChicago

EGE - ORD

EGEORD

Vail Eagle County

Thu 1/8

10:57 am-2:47 pm

Nonstop2h 50m

Chicago O'Hare Intl

Sun 1/11

8:24 am-10:31 am

Nonstop3h 07m

$381

VailChicago

EGE - ORD

EGEORD

Vail Eagle County

Thu 1/8

12:13 pm-9:07 pm

1 stop7h 54m

Chicago O'Hare Intl

Sun 1/11

8:24 am-10:31 am

Nonstop3h 07m

$391

VailChicago

EGE - ORD

EGEORD

Vail Eagle County

Thu 1/8

3:10 pm-11:59 pm

1 stop7h 49m

Chicago O'Hare Intl

Sun 1/11

5:30 am-2:05 pm

1 stop9h 35m

$401

VailChicago

EGE - ORD

EGEORD

Vail Eagle County

Sat 2/14

8:00 am-12:00 pm

Nonstop3h 00m

Chicago O'Hare Intl

Tue 2/17

12:45 pm-2:52 pm

Nonstop3h 07m

$440

VailChicago

EGE - ORD

EGEORD

Vail Eagle County

Sat 2/14

2:39 pm-11:59 pm

1 stop8h 20m

Chicago O'Hare Intl

Tue 2/17

3:07 pm-4:56 pm

1 stop26h 49m

$443

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

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 Thursday when prices can be found for as low as $301. 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 $518.

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 $199. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $617.

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 36% 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

$260

Fastest flight time

2h 53m

Direct flights

Every day

Airports in Chicago

3 airports
The best one-way flight to Chicago from Vail in the past 72 hours is $260. The best round-trip flight deal from Vail to Chicago found on momondo in the last 72 hours is $388.
The fastest flight from Vail to Chicago takes 2h 53m
Direct flights go from Vail to Chicago every day.
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 53m.

  • 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
9,105 reviews
Search United Airlines flights
American AirlinesPriceFrom $359Free CancellationRating
7.2
11,054 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 14 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 $359, 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 11 flights out of Vail into Chicago in an average week, so prices vary by time and availability. 11,054 American Airlines reviews by users on momondo have scored the airline at 7.2/10.

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
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.

An easier way to manage your Chicago trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Thu 1/22
Thu 1/29
By creating a price alert you accept our terms of use and privacy policy.

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