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Vail

$131+ Cheap flights from Chicago (CHI) to Vail (EGE)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11/18. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — EGE
août 25 — sept. 11
lun. 8/25
lun. 9/1
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Vail Eagle County are usually found in April or January, booked 23 days in advance, depart on a Wednesday or Friday and return on a Tuesday

Cheap flight deals from Chicago to Vail

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Vail (EGE). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated août 20, 2025.

Round-trip from

$229
(United Airlines)

One-way from

$131
(American Airlines)

Popular in

July

Cheapest in

April

Average price

$551

Good round-trip deal

$449 or less
From Chicago (CHI) to Vail Eagle County
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One-way flight from Chicago (CHI) to Vail Eagle County
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Highest demand for flights based on searches. 10% potential increase in price ($66 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($10 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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Price to beat on a round-trip flight from Chicago (CHI) to Vail Eagle County.
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Find flight deals from Chicago to Vail

Cheapest flights from Chicago to Vail
Explore the most affordable flight options available from Chicago to Vail. Find the lowest fares from popular airlines and budget airlines, with prices last updated on août 20, 2025.

This United Airlines deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sam. 9/134:10 pmORD - EGE
Nonstop2h 53mUnited Airlines
sam. 9/208:50 amEGE - ORD
Nonstop2h 51mUnited Airlines
Deal found 8/20$229
This United Airlines deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 9/297:10 amORD - EGE
1 stop6h 28mUnited Airlines
sam. 10/41:30 pmEGE - ORD
1 stop7h 00mUnited Airlines
Deal found 8/18$271
This American Airlines deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mer. 11/191:21 pmORD - EGE
1 stop6h 50mAmerican Airlines
lun. 11/248:00 amEGE - ORD
1 stop8h 15mAmerican Airlines
Deal found 8/18$289
This United Airlines deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ven. 9/124:10 pmORD - EGE
Nonstop2h 53mUnited Airlines
dim. 9/141:40 pmEGE - ORD
1 stop6h 01mUnited Airlines
Deal found 8/18$294
This United Airlines deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jeu. 10/22:17 pmORD - EGE
1 stop6h 51mUnited Airlines
sam. 10/41:30 pmEGE - ORD
1 stop5h 48mUnited Airlines
Deal found 8/18$305
This American Airlines deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jeu. 12/258:00 amORD - EGE
Nonstop3h 05mAmerican Airlines
lun. 12/2910:45 amEGE - ORD
Nonstop2h 30mAmerican Airlines
Deal found 8/17$309
This United Airlines deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ven. 9/124:10 pmORD - EGE
Nonstop2h 53mUnited Airlines
lun. 9/153:15 pmEGE - ORD
1 stop7h 44mUnited Airlines
Deal found 8/17$319
This American Airlines deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jeu. 12/188:00 amORD - EGE
Nonstop3h 05mAmerican Airlines
lun. 12/2210:45 amEGE - ORD
Nonstop2h 30mAmerican Airlines
Deal found 8/18$325

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to Vail 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, Cheapflights users made 2,558,603 searches. Data last updated août 20, 2025.
Use the filters below to find and compare flights from Chicago to Vail that are best for you.

Fly from

Chicago

Fly to

Vail

Route

Depart

Return

Price

ChicagoVail

ORD - EGE

ORDEGE

Chicago O'Hare Intl

sam. 9/13

4:10 pm-6:03 pm

Nonstop2h 53m

Vail Eagle County

sam. 9/20

8:50 am-12:41 pm

Nonstop2h 51m

$229

ChicagoVail

ORD - EGE

ORDEGE

Chicago O'Hare Intl

mer. 10/15

1:22 pm-6:54 pm

1 stop6h 32m

Vail Eagle County

sam. 10/18

8:08 am-5:10 pm

1 stop8h 02m

$249

ChicagoVail

ORD - EGE

ORDEGE

Chicago O'Hare Intl

mer. 10/1

11:54 am-6:37 pm

1 stop7h 43m

Vail Eagle County

sam. 10/4

8:12 am-5:18 pm

1 stop8h 06m

$249

ChicagoVail

ORD - EGE

ORDEGE

Chicago O'Hare Intl

mar. 9/30

11:54 am-6:37 pm

1 stop7h 43m

Vail Eagle County

sam. 10/4

8:12 am-5:18 pm

1 stop8h 06m

$249

ChicagoVail

ORD - EGE

ORDEGE

Chicago O'Hare Intl

lun. 9/29

7:10 am-12:38 pm

1 stop6h 28m

Vail Eagle County

sam. 10/4

1:30 pm-9:30 pm

1 stop7h 00m

$271

ChicagoVail

ORD - EGE

ORDEGE

Chicago O'Hare Intl

ven. 9/12

4:10 pm-6:03 pm

Nonstop2h 53m

Vail Eagle County

dim. 9/14

1:40 pm-8:41 pm

1 stop6h 01m

$294

ChicagoVail

ORD - EGE

ORDEGE

Chicago O'Hare Intl

jeu. 10/2

2:17 pm-8:08 pm

1 stop6h 51m

Vail Eagle County

sam. 10/4

1:30 pm-8:18 pm

1 stop5h 48m

$305

ChicagoVail

ORD - EGE

ORDEGE

Chicago O'Hare Intl

ven. 9/12

4:10 pm-6:03 pm

Nonstop2h 53m

Vail Eagle County

lun. 9/15

3:15 pm-11:59 pm

1 stop7h 44m

$319

ChicagoVail

ORD - EGE

ORDEGE

Chicago O'Hare Intl

mar. 11/18

1:21 pm-7:11 pm

1 stop6h 50m

$131

ChicagoVail

ORD - EGE

ORDEGE

Chicago O'Hare Intl

ven. 10/17

1:26 pm-6:56 pm

1 stop6h 30m

$221

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/19

Showing 1-10 of 18 results
1
2

Best time to book a flight from Chicago to Vail

Have a flexible travel schedule? Discover the best time to fly to Vail from Chicago with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Chicago to Vail

How far ahead should I book a flight from Chicago to Vail?

Use this chart to determine the optimal time to book a round-trip flight from Chicago to Vail. Price data was last updated on August 8, 2025.

The price you pay for your flight from Chicago to Vail may vary depending on when you book. For the best chance of a lower fare, look to book 23 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

What is the cheapest month to book a flight from Chicago to Vail?

Currently, October is the cheapest month in which you can book a flight from Chicago to Vail (average of $448). Flying from Chicago to Vail in December is currently the most expensive (average of $621). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from CHI to EGE?

Find hourly flight availability from Chicago to Vail. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated août 20, 2025.

A simple way to save on the total cost of your ticket is to fly from Chicago to Vail in the afternoon. If you’re flexible enough to do this you can expect to save up to 15% on your trip compared to booking a flight in the evening.

Reviews of airlines servicing Vail

Get insights into the airlines that provide service to Vail. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Vail. Reviews last updated août 20, 2025.
Get a feel of what it's like to fly with United Airlines, American Airlines, and Frontier from Chicago to Vail by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
8,928 reviews

Comfort

7.3

Overall

7.4

Boarding

7.7

Crew

8.1

Food

6.6

Entertainment

7.1

Reviews

1 / 20
8.0
Excellent

Ruth,Dec 2024

ORD - AMS

United Airlines flights seem to always use a bus to/from the boarding gate to the plane. Can they not get their own gate? This time there was no lift when leaving the plane and people in wheelchairs somehow had to climb down the steps to the ground to get to the bus. I udon’t know how some managed that!
United Airlines
7.4
Good
8,928 reviews
United Airlines
7.4
Good
8,928 reviews

Comfort

7.3

Overall

7.4

Boarding

7.7

Crew

8.1

Food

6.6

Entertainment

7.1

Reviews

1 / 20
8.0
Excellent

Ruth,Dec 2024

ORD - AMS

United Airlines flights seem to always use a bus to/from the boarding gate to the plane. Can they not get their own gate? This time there was no lift when leaving the plane and people in wheelchairs somehow had to climb down the steps to the ground to get to the bus. I udon’t know how some managed that!
American Airlines
7.2
Good
10,000 reviews
United Airlines
7.4
Good
8,928 reviews

Comfort

7.3

Overall

7.4

Boarding

7.7

Crew

8.1

Food

6.6

Entertainment

7.1

Reviews

1 / 20
8.0
Excellent

Ruth,Dec 2024

ORD - AMS

United Airlines flights seem to always use a bus to/from the boarding gate to the plane. Can they not get their own gate? This time there was no lift when leaving the plane and people in wheelchairs somehow had to climb down the steps to the ground to get to the bus. I udon’t know how some managed that!
Frontier
5.8
Fair
3,207 reviews
United Airlines
7.4
Good
8,928 reviews

Comfort

7.3

Overall

7.4

Boarding

7.7

Crew

8.1

Food

6.6

Entertainment

7.1

Reviews

1 / 20
8.0
Excellent

Ruth,Dec 2024

ORD - AMS

United Airlines flights seem to always use a bus to/from the boarding gate to the plane. Can they not get their own gate? This time there was no lift when leaving the plane and people in wheelchairs somehow had to climb down the steps to the ground to get to the bus. I udon’t know how some managed that!

Related info for your journey

Find useful and relevant information for your journey from Chicago to Vail. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to Vail from Chicago?

    Vail Eagle County (EGE) is the airport you will fly into if you book a flight from Chicago to Vail. You should not have trouble finding flights to Eagle County from Chicago; the airport handles an average of 0 inbound flights from Chicago per day. You should also have plenty of airline options to choose from since 2 airlines have flights to the Vail airport from Chicago. It is only a 28.9 mi journey from Eagle County (EGE) to Vail’s city center.

  • How long is the flight from Chicago to Vail?

    There are many flights that can get you from Chicago to Vail in 2h 53m. Fly via United Airlines or American Airlines to get the fastest option. The distance between Chicago and Vail is about 1004 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the cheapest airlines flying from Chicago to Vail round-trip?

    Flying on American Airlines is currently your cheapest option to Vail, with prices starting at $324. Another option worth looking into is United Airlines, starting at $380 round trip. American Airlines is priced at 42% lower than the current average price of a flight leaving 3 months from now.

  • What are the cheapest flights from Chicago to Vail?

    The cheapest flight price from Chicago to Vail is $289. On average you can expect to pay $529. The most popular route, (Chicago O'Hare Intl - Vail Eagle County), can usually be booked for $229.

  • Can I find deals for flights from Chicago to Vail that include hotel bookings?

    Yes. In addition to deals on Chicago to Vail flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Vail?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Vail.

  • Can I find deals for business class flights from Chicago to Vail?

    Yes. Cheapflights offers flight deals from Chicago to Vail by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago to Vail?

    Currently, October is the cheapest month in which you can book a flight from Chicago to Vail (average of $448). Flying from Chicago to Vail in December is currently the most expensive (average of $621). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Vail?

Book flights to Vail if you plan to visit one of these locations
Eagle
Beaver Creek
Avon
Rifle

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Alternative routes for Chicago to Vail

See prices for flight routes from nearby airports that may be better suited for you.
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Top 2 airlines flying from Chicago to Vail

Discover the top 2 airlines that operate flights from Chicago to Vail. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated août 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$324Average$505FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$380Average$586FlexibilityNo cancel feeOn-time69%

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