What is the cheapest airline that flies from Vail Eagle County to Chicago?

United Airlines, Delta, and American Airlines are the most popular carriers operating from Vail Eagle County to Chicago

What airlines fly to Chicago?

United Airlines, American Airlines and Frontier are the top three most popular airlines that fly to Chicago from Vail according to our data. United Airlines is the first choice among our users, with 41% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 5 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

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?

As of November 2026, there are 2 operators available to choose from 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.

$248 Cheap Flights from Vail to Chicago in 2026/27

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Vail to Chicago

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

8:00 am - 12:00 pmEGE Vail Eagle County-ORD Chicago O'Hare Intl

3h 00mnonstop

8:40 am - 10:51 amORD Chicago O'Hare Intl-EGE Vail Eagle County

3h 11mnonstop

$497United Airlines

Sat, Jan 16 - Mon, Jan 18

8:00 am - 12:00 pmEGE Vail Eagle County-ORD Chicago O'Hare Intl

3h 00mnonstop

8:40 am - 10:51 amORD Chicago O'Hare Intl-EGE Vail Eagle County

3h 11mnonstop

$497United Airlines

Sat, Jan 16 - Mon, Jan 18

1:35 pm - 9:34 pmEGE Vail Eagle County-ORD Chicago O'Hare Intl

6h 59m1 stop Denver Intl

9:00 am - 11:07 amORD Chicago O'Hare Intl-EGE Vail Eagle County

3h 07mnonstop

$503United Airlines

Fri, Dec 11 - Sat, Dec 12

8:00 am - 12:00 pmEGE Vail Eagle County-ORD Chicago O'Hare Intl

3h 00mnonstop

2:24 pm - 8:33 pmORD Chicago O'Hare Intl-EGE Vail Eagle County

7h 09m1 stop Denver Intl

$507United Airlines

Sat, Jan 16 - Mon, Jan 18

3:26 pm - 10:20 pmEGE Vail Eagle County-ORD Chicago O'Hare Intl

5h 54m1 stop Atlanta Hartsfield-Jackson

7:10 am - 1:03 pmORD Chicago O'Hare Intl-EGE Vail Eagle County

6h 53m1 stop Atlanta Hartsfield-Jackson

$515Delta

Sat, Jan 16 - Mon, Jan 18

3:26 pm - 10:20 pmEGE Vail Eagle County-ORD Chicago O'Hare Intl

5h 54m1 stop Atlanta Hartsfield-Jackson

7:10 am - 1:03 pmORD Chicago O'Hare Intl-EGE Vail Eagle County

6h 53m1 stop Atlanta Hartsfield-Jackson

$515Delta

Sat, Jan 16 - Mon, Jan 18

11:32 am - 10:20 pmEGE Vail Eagle County-ORD Chicago O'Hare Intl

9h 48m2 stops Minneapolis St Paul Atlanta Hartsfield-Jackson

7:10 am - 1:03 pmORD Chicago O'Hare Intl-EGE Vail Eagle County

6h 53m1 stop Atlanta Hartsfield-Jackson

$520Delta

Sat, Jan 16 - Mon, Jan 18

12:34 pm - 4:29 pmEGE Vail Eagle County-ORD Chicago O'Hare Intl

2h 55mnonstop

9:40 am - 11:54 amORD Chicago O'Hare Intl-EGE Vail Eagle County

3h 14mnonstop

$572American Airlines

Sat, Jan 16 - Mon, Jan 18

2:08 pm - 10:31 pmEGE Vail Eagle County-ORD Chicago O'Hare Intl

7h 23m1 stop Dallas/Fort Worth

9:40 am - 11:54 amORD Chicago O'Hare Intl-EGE Vail Eagle County

3h 14mnonstop

$582American Airlines

Sat, Jan 16 - Mon, Jan 18

8:00 am - 8:20 pmEGE Vail Eagle County-ORD Chicago O'Hare Intl

11h 20m2 stops Dallas/Fort Worth Wichita Eisenhower National

1:43 pm - 7:15 pmORD Chicago O'Hare Intl-EGE Vail Eagle County

6h 32m1 stop Dallas/Fort Worth

$627American Airlines

Fri, Dec 11 - Sat, Dec 12

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United Airlines flights from Vail to Chicago

Our best United Airlines deals on Vail to Chicago flight tickets

United Airlines

Jan 16

EGE8:00 amVail Eagle County

3h 00m

ORD12:00 pmChicago O'Hare Intl

Jan 18

ORD8:40 amChicago O'Hare Intl

3h 11m

EGE10:51 amVail Eagle County

$497

United Airlines

Jan 16

EGE8:00 amVail Eagle County

3h 00m

ORD12:00 pmChicago O'Hare Intl

Jan 18

ORD2:24 pmChicago O'Hare Intl

7h 09m

1 stop

EGE8:33 pmVail Eagle County

$507

United Airlines

Nov 19

EGE1:31 pmVail Eagle County

5h 34m

1 stop

ORD8:05 pmChicago O'Hare Intl

Nov 22

ORD7:00 amChicago O'Hare Intl

6h 26m

1 stop

EGE12:26 pmVail Eagle County

$595

Delta flights from Vail to Chicago

Our best Delta deals on Vail to Chicago flight tickets

Delta

Jan 16

EGE3:26 pmVail Eagle County

5h 54m

1 stop

ORD10:20 pmChicago O'Hare Intl

Jan 18

ORD7:10 amChicago O'Hare Intl

6h 53m

1 stop

EGE1:03 pmVail Eagle County

$515

Delta

Jan 16

EGE11:32 amVail Eagle County

9h 48m

2 stops

ORD10:20 pmChicago O'Hare Intl

Jan 18

ORD7:10 amChicago O'Hare Intl

6h 53m

1 stop

EGE1:03 pmVail Eagle County

$520

Delta

Jan 16

EGE11:32 amVail Eagle County

9h 48m

2 stops

ORD10:20 pmChicago O'Hare Intl

Jan 18

ORD7:10 amChicago O'Hare Intl

6h 53m

1 stop

EGE1:03 pmVail Eagle County

$552

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

Sat 1/16

8:00 am-12:00 pm

Nonstop3h 00m

Chicago O'Hare Intl

Mon 1/18

8:40 am-10:51 am

Nonstop3h 11m

$497

VailChicago

EGE Vail Eagle County - ORD Chicago O'Hare Intl

EGEORD

Vail Eagle County

Sat 1/16

8:00 am-12:00 pm

Nonstop3h 00m

Chicago O'Hare Intl

Mon 1/18

8:40 am-10:51 am

Nonstop3h 11m

$497

VailChicago

EGE Vail Eagle County - ORD Chicago O'Hare Intl

EGEORD

Vail Eagle County

Fri 12/11

1:35 pm-9:34 pm

1 stop6h 59m

Chicago O'Hare Intl

Sat 12/12

9:00 am-11:07 am

Nonstop3h 07m

$503

VailChicago

EGE Vail Eagle County - ORD Chicago O'Hare Intl

EGEORD

Vail Eagle County

Sat 1/16

8:00 am-12:00 pm

Nonstop3h 00m

Chicago O'Hare Intl

Mon 1/18

2:24 pm-8:33 pm

1 stop7h 09m

$507

VailChicago

EGE Vail Eagle County - ORD Chicago O'Hare Intl

EGEORD

Vail Eagle County

Sat 1/16

3:26 pm-10:20 pm

1 stop5h 54m

Chicago O'Hare Intl

Mon 1/18

7:10 am-1:03 pm

1 stop6h 53m

$515

VailChicago

EGE Vail Eagle County - ORD Chicago O'Hare Intl

EGEORD

Vail Eagle County

Sat 1/16

3:26 pm-10:20 pm

1 stop5h 54m

Chicago O'Hare Intl

Mon 1/18

7:10 am-1:03 pm

1 stop6h 53m

$515

VailChicago

EGE Vail Eagle County - ORD Chicago O'Hare Intl

EGEORD

Vail Eagle County

Sat 1/16

11:32 am-10:20 pm

2 stops9h 48m

Chicago O'Hare Intl

Mon 1/18

7:10 am-1:03 pm

1 stop6h 53m

$520

Quickest round-trip

VailChicago

EGE Vail Eagle County - ORD Chicago O'Hare Intl

EGEORD

Vail Eagle County

Sat 1/16

12:34 pm-4:29 pm

Nonstop2h 55m

Chicago O'Hare Intl

Mon 1/18

9:40 am-11:54 am

Nonstop3h 14m

$572

VailChicago

EGE Vail Eagle County - ORD Chicago O'Hare Intl

EGEORD

Vail Eagle County

Sat 1/16

2:08 pm-10:31 pm

1 stop7h 23m

Chicago O'Hare Intl

Mon 1/18

9:40 am-11:54 am

Nonstop3h 14m

$582

VailChicago

EGE Vail Eagle County - ORD Chicago O'Hare Intl

EGEORD

Vail Eagle County

Fri 12/11

8:00 am-8:20 pm

2 stops11h 20m

Chicago O'Hare Intl

Sat 12/12

1:43 pm-7:15 pm

1 stop6h 32m

$627

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

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

Prices

Airlines

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 $360.

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 $411. 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 $560.

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 5% 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	$248
Fastest flight time	2h 57m
Direct flights	Mon, Tue, Wed and Sun
Airports in Chicago	3 airports

The best one-way flight to Chicago from Vail in the past 72 hours is $248. The best round-trip flight deal from Vail to Chicago found on momondo in the last 72 hours is $497.

The fastest flight from Vail to Chicago takes 2h 57m

Direct flights go from Vail to Chicago on Monday, Tuesday, Wednesday 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 57m.
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?
As of November 2026, there are 2 operators available to choose from 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?
momondo data reveals that the most frequently booked plane model on the route from Vail to Chicago is Airbus A319, representing 22.22% of all bookings. The subsequent popular models are Boeing 757-200 at 22.22%, Embraer 175 (Enhanced Winglets) at 11.11%, and Airbus A220-300 at 11.11%.
What is the most popular airline from Vail to Chicago?
momondo data reveals that the most frequently booked airline on the route from Vail to Chicago is United Airlines, representing 100% of all bookings.

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
American Airlines	PriceFrom $265	Free Cancellation	Rating 7.0 12,224 reviews		Search American Airlines flights
United Airlines	PriceFrom $374	Free Cancellation	Rating 7.3 10,471 reviews		Search United Airlines flights

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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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Cheap flights from Vail to Chicago from $248

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 1/15. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

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United Airlines flights from Vail to Chicago

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How to get the cheapest flight ticket from Vail to Chicago

What is the cheapest month to fly to Chicago?

What is the cheapest day to depart on your flight to Chicago?

What is the cheapest Vail Eagle County to Chicago flight route?

What cabin class options are available on Vail to Chicago flights?

Can stopping save me money on Vail to Chicago flights?

What is the cheapest airline that flies from Vail Eagle County to Chicago?

What airlines fly to Chicago?

When to book flights from Vail to Chicago

Cheap Vail to Chicago (EGE to CHI) flight deals and tips

Best Price Found

Fastest flight time

Direct flights

Airports in Chicago

Frequently asked questions about flying 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

Traveling to a place near Chicago?

Why use momondo?

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.

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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

Fly your favorite airline to Chicago

Airlines are sorted and displayed according to clicks in the past 7 days on momondo

Cabin classes currently available on flights to Chicago

List of cabin classes available on flights landing in Chicago. Availability may vary depending on flight origin and airline.

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