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Cheap flights from Vail to Chicago from $203

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 2/4. 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.
American Airlines Logo
8:00 am - 4:00 pmEGE  Vail Eagle County-ORD Chicago O'Hare Intl
7h 00m1 stop Dallas/Fort Worth
American Airlines Logo
9:24 am - 7:01 pmORD  Chicago O'Hare Intl-EGE Vail Eagle County
10h 37m2 stops Lambert-St Louis Dallas/Fort Worth
$398American Airlines
Thu, Nov 12 - Mon, Nov 16
American Airlines Logo
12:58 pm - 10:04 pmEGE  Vail Eagle County-ORD Chicago O'Hare Intl
8h 06m1 stop Dallas/Fort Worth
American Airlines Logo
5:00 am - 12:17 pmORD  Chicago O'Hare Intl-EGE Vail Eagle County
8h 17m1 stop Dallas/Fort Worth
$425American Airlines
Tue, Sep 15 - Sun, Sep 20
American Airlines Logo
8:00 am - 4:00 pmEGE  Vail Eagle County-ORD Chicago O'Hare Intl
7h 00m1 stop Dallas/Fort Worth
American Airlines Logo
12:02 pm - 7:01 pmORD  Chicago O'Hare Intl-EGE Vail Eagle County
7h 59m1 stop Dallas/Fort Worth
$425American Airlines
Thu, Nov 12 - Mon, Nov 16
American Airlines Logo
12:58 pm - 8:29 pmEGE  Vail Eagle County-ORD Chicago O'Hare Intl
6h 31m1 stop Dallas/Fort Worth
American Airlines Logo
6:00 am - 12:17 pmORD  Chicago O'Hare Intl-EGE Vail Eagle County
7h 17m1 stop Dallas/Fort Worth
$425American Airlines
Fri, Sep 11 - Sun, Sep 13
United Airlines Logo
8:00 am - 11:59 amEGE  Vail Eagle County-ORD Chicago O'Hare Intl
2h 59mnonstop
United Airlines Logo
10:55 am - 2:27 pmORD  Chicago O'Hare Intl-EGE Vail Eagle County
4h 32m1 stop Denver Intl
$509United Airlines
Sat, Sep 5 - Tue, Sep 8
United Airlines Logo
1:31 pm - 8:05 pmEGE  Vail Eagle County-ORD Chicago O'Hare Intl
5h 34m1 stop Denver Intl
United Airlines Logo
4:20 pm - 8:31 pmORD  Chicago O'Hare Intl-EGE Vail Eagle County
5h 11m1 stop Denver Intl
$519United Airlines
Fri, Nov 13 - Tue, Nov 17
United Airlines Logo
3:29 pm - 9:30 pmEGE  Vail Eagle County-ORD Chicago O'Hare Intl
5h 01m1 stop Denver Intl
United Airlines Logo
4:00 pm - 6:02 pmORD  Chicago O'Hare Intl-EGE Vail Eagle County
3h 02mnonstop
$519United Airlines
Wed, Sep 16 - Sat, Sep 19
United Airlines Logo
3:29 pm - 9:29 pmEGE  Vail Eagle County-ORD Chicago O'Hare Intl
5h 00m1 stop Denver Intl
United Airlines Logo
4:00 pm - 6:02 pmORD  Chicago O'Hare Intl-EGE Vail Eagle County
3h 02mnonstop
$550United Airlines
Thu, Sep 3 - Sun, Sep 6
Delta Logo
11:30 am - 8:43 amEGE  Vail Eagle County-ORD Chicago O'Hare Intl
20h 13m1 stop Minneapolis St Paul
Delta Logo
5:30 am - 10:46 amORD  Chicago O'Hare Intl-EGE Vail Eagle County
6h 16m1 stop Atlanta Hartsfield-Jackson
$694Delta
Wed, Dec 23 - Mon, Dec 28
Delta Logo
11:30 am - 11:50 pmEGE  Vail Eagle County-ORD Chicago O'Hare Intl
11h 20m2 stops Minneapolis St Paul Atlanta Hartsfield-Jackson
Delta Logo
5:30 am - 10:46 amORD  Chicago O'Hare Intl-EGE Vail Eagle County
6h 16m1 stop Atlanta Hartsfield-Jackson
$872Delta
Wed, Dec 23 - Mon, Dec 28

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United Airlines flights from Vail to Chicago

Our best United Airlines deals on Vail to Chicago flight tickets
United Airlines
Sep 5
EGE8:00 amVail Eagle County
2h 59m
ORD11:59 amChicago O'Hare Intl
Sep 8
ORD10:55 amChicago O'Hare Intl
4h 32m
1 stop
EGE2:27 pmVail Eagle County
$509
United Airlines
Sep 3
EGE3:29 pmVail Eagle County
5h 00m
1 stop
ORD9:29 pmChicago O'Hare Intl
Sep 6
ORD4:00 pmChicago O'Hare Intl
3h 02m
EGE6:02 pmVail Eagle County
$550
United Airlines
Oct 9
EGE3:31 pmVail Eagle County
7h 28m
1 stop
ORD11:59 pmChicago O'Hare Intl
Oct 12
ORD4:20 pmChicago O'Hare Intl
5h 13m
1 stop
EGE8:33 pmVail Eagle County
$555

American Airlines flights from Vail to Chicago

Our best American Airlines deals on Vail to Chicago flight tickets
American Airlines
Nov 12
EGE8:00 amVail Eagle County
7h 00m
1 stop
ORD4:00 pmChicago O'Hare Intl
Nov 16
ORD9:24 amChicago O'Hare Intl
10h 37m
2 stops
EGE7:01 pmVail Eagle County
$398
American Airlines
Sep 15
EGE12:58 pmVail Eagle County
8h 06m
1 stop
ORD10:04 pmChicago O'Hare Intl
Sep 20
ORD5:00 amChicago O'Hare Intl
8h 17m
1 stop
EGE12:17 pmVail Eagle County
$425
American Airlines
Sep 16
EGE12:58 pmVail Eagle County
16h 31m
2 stops
ORD6:29 amChicago O'Hare Intl
Sep 19
ORD1:46 pmChicago O'Hare Intl
5h 57m
1 stop
EGE6:43 pmVail Eagle County
$445

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 August 8, 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 Vail Eagle County - ORD Chicago O'Hare Intl

EGEORD

Vail Eagle County

Thu 11/12

8:00 am-4:00 pm

1 stop7h 00m

Chicago O'Hare Intl

Mon 11/16

9:24 am-7:01 pm

2 stops10h 37m

$398

VailChicago

EGE Vail Eagle County - ORD Chicago O'Hare Intl

EGEORD

Vail Eagle County

Tue 9/15

12:58 pm-10:04 pm

1 stop8h 06m

Chicago O'Hare Intl

Sun 9/20

5:00 am-12:17 pm

1 stop8h 17m

$425

VailChicago

EGE Vail Eagle County - ORD Chicago O'Hare Intl

EGEORD

Vail Eagle County

Thu 11/12

8:00 am-4:00 pm

1 stop7h 00m

Chicago O'Hare Intl

Mon 11/16

12:02 pm-7:01 pm

1 stop7h 59m

$425

VailChicago

EGE Vail Eagle County - ORD Chicago O'Hare Intl

EGEORD

Vail Eagle County

Fri 9/11

12:58 pm-8:29 pm

1 stop6h 31m

Chicago O'Hare Intl

Sun 9/13

6:00 am-12:17 pm

1 stop7h 17m

$425
Quickest round-trip

VailChicago

EGE Vail Eagle County - ORD Chicago O'Hare Intl

EGEORD

Vail Eagle County

Sat 9/5

8:00 am-11:59 am

Nonstop2h 59m

Chicago O'Hare Intl

Tue 9/8

10:55 am-2:27 pm

1 stop4h 32m

$509

VailChicago

EGE Vail Eagle County - ORD Chicago O'Hare Intl

EGEORD

Vail Eagle County

Fri 11/13

1:31 pm-8:05 pm

1 stop5h 34m

Chicago O'Hare Intl

Tue 11/17

4:20 pm-8:31 pm

1 stop5h 11m

$519

VailChicago

EGE Vail Eagle County - ORD Chicago O'Hare Intl

EGEORD

Vail Eagle County

Wed 9/16

3:29 pm-9:30 pm

1 stop5h 01m

Chicago O'Hare Intl

Sat 9/19

4:00 pm-6:02 pm

Nonstop3h 02m

$519

VailChicago

EGE Vail Eagle County - ORD Chicago O'Hare Intl

EGEORD

Vail Eagle County

Thu 9/3

3:29 pm-9:29 pm

1 stop5h 00m

Chicago O'Hare Intl

Sun 9/6

4:00 pm-6:02 pm

Nonstop3h 02m

$550

VailChicago

EGE Vail Eagle County - ORD Chicago O'Hare Intl

EGEORD

Vail Eagle County

Wed 12/23

11:30 am-8:43 am

1 stop20h 13m

Chicago O'Hare Intl

Mon 12/28

5:30 am-10:46 am

1 stop6h 16m

$694

VailChicago

EGE Vail Eagle County - ORD Chicago O'Hare Intl

EGEORD

Vail Eagle County

Wed 12/23

11:30 am-11:50 pm

2 stops11h 20m

Chicago O'Hare Intl

Mon 12/28

5:30 am-10:46 am

1 stop6h 16m

$872

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 $331.

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 $566.

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 3 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 30% 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

$452

Fastest flight time

4h 55m

Direct flights

Mon, Tue, Thu, Fri and Sun

Airports in Chicago

3 airports
The best flight deal from Vail to Chicago found on momondo in the last 72 hours is $452
The fastest flight from Vail to Chicago takes 4h 55m
Direct flights go from Vail to Chicago on Monday, Tuesday, 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

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 4h 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
10,085 reviews
Search United Airlines flights
American AirlinesPriceFrom $265Free CancellationRating
7.1
11,885 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
Lansing
Saint Joseph
Valparaiso
Schererville
Munster
Chesterton
Monticello
Crown Point
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