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Vail

$221+ 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 2/6. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — EGE
Nov 29 — Dec 61
Sat 11/29
Sat 12/6
1 adult, Economy
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1. Tell us where you want to go

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Cheapflights Tip: The best prices from Chicago to Vail Eagle County are usually found in April or December, booked 31 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 October 30, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$331
(American Airlines)

One-way from

$221
(American Airlines)

Popular in

July

Cheapest in

April

Average price

$661

Good round-trip deal

$349 or less
Provider with most accurate pricing for Chicago (CHI)-Vail Eagle County flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Vail Eagle County flights.
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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. 7% potential increase in price ($47 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 October 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 October 30, 2025.

This American Airlines deal was found by Cheapflights users on 10/28. 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.
Wed 11/191:23 pmORD - EGE
1 stop6h 48mAmerican Airlines
Mon 11/248:00 amEGE - ORD
1 stop8h 15mAmerican Airlines
Deal found 10/28$341
This United Airlines deal was found by Cheapflights users on 10/29. 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.
Thu 12/189:00 amORD - EGE
Nonstop3h 04mUnited Airlines
Sat 12/2712:20 pmEGE - ORD
Nonstop2h 55mUnited Airlines
Deal found 10/29$349
This American Airlines deal was found by Cheapflights users on 10/30. 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.
Thu 12/185:00 amORD - EGE
1 stop8h 11mAmerican Airlines
Mon 12/2210:12 amEGE - ORD
1 stop8h 25mAmerican Airlines
Deal found 10/30$369
This United Airlines deal was found by Cheapflights users on 10/28. 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.
Sun 11/168:47 amORD - EGE
1 stop4h 37mUnited Airlines
Tue 11/183:15 pmEGE - ORD
1 stop7h 44mUnited Airlines
Deal found 10/28$372
This United Airlines deal was found by Cheapflights users on 10/30. 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.
Sat 12/204:20 pmORD - EGE
Nonstop3h 01mUnited Airlines
Wed 12/243:30 pmEGE - ORD
1 stop4h 49mUnited Airlines
Deal found 10/30$379
This American Airlines deal was found by Cheapflights users on 10/29. 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.
Thu 11/1311:46 amORD - EGE
1 stop8h 25mAmerican Airlines
Mon 11/178:00 amEGE - ORD
1 stop8h 17mAmerican Airlines
Deal found 10/29$388
This United Airlines deal was found by Cheapflights users on 10/29. 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.
Thu 11/202:40 pmORD - EGE
1 stop6h 51mUnited Airlines
Sun 11/233:15 pmEGE - ORD
1 stop7h 44mUnited Airlines
Deal found 10/29$393
This American Airlines deal was found by Cheapflights users on 10/28. 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.
Thu 12/1810:45 amORD - EGE
Nonstop3h 06mAmerican Airlines
Sat 12/2710:34 amEGE - ORD
Nonstop3h 00mAmerican Airlines
Deal found 10/28$395
This United Airlines deal was found by Cheapflights users on 10/28. 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.
Mon 12/224:20 pmORD - EGE
Nonstop3h 01mUnited Airlines
Fri 12/268:25 amEGE - ORD
Nonstop3h 04mUnited Airlines
Deal found 10/28$411
This United Airlines deal was found by Cheapflights users on 10/28. 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.
Sat 11/87:10 amORD - EGE
1 stop6h 14mUnited Airlines
Mon 11/101:30 pmEGE - ORD
1 stop5h 10mUnited Airlines
Deal found 10/28$413

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 October 30, 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

Tue 1/6

9:15 am-11:27 am

Nonstop3h 12m

Vail Eagle County

Sat 1/10

8:30 am-12:34 pm

Nonstop3h 04m

$340

ChicagoVail

ORD - EGE

ORDEGE

Chicago O'Hare Intl

Mon 1/5

5:00 am-10:49 am

1 stop6h 49m

Vail Eagle County

Fri 1/9

10:57 am-2:47 pm

Nonstop2h 50m

$341

ChicagoVail

ORD - EGE

ORDEGE

Chicago O'Hare Intl

Tue 1/6

9:15 am-11:27 am

Nonstop3h 12m

Vail Eagle County

Tue 1/13

3:31 pm-9:15 pm

1 stop4h 44m

$341

ChicagoVail

ORD - EGE

ORDEGE

Chicago O'Hare Intl

Thu 12/18

9:00 am-11:04 am

Nonstop3h 04m

Vail Eagle County

Sat 12/27

12:20 pm-4:15 pm

Nonstop2h 55m

$349

ChicagoVail

ORD - EGE

ORDEGE

Chicago O'Hare Intl

Fri 1/2

9:00 am-11:04 am

Nonstop3h 04m

Vail Eagle County

Wed 1/7

1:42 pm-7:51 pm

1 stop5h 09m

$350

ChicagoVail

ORD - EGE

ORDEGE

Chicago O'Hare Intl

Mon 1/5

6:12 am-10:57 am

1 stop5h 45m

Vail Eagle County

Fri 1/9

3:10 pm-11:57 pm

1 stop7h 47m

$351

ChicagoVail

ORD - EGE

ORDEGE

Chicago O'Hare Intl

Sun 1/11

7:05 am-2:05 pm

1 stop8h 00m

Vail Eagle County

Sat 1/17

11:37 am-11:57 pm

2 stops11h 20m

$365

ChicagoVail

ORD - EGE

ORDEGE

Chicago O'Hare Intl

Sat 12/20

4:20 pm-6:21 pm

Nonstop3h 01m

Vail Eagle County

Mon 12/29

8:25 am-12:29 pm

Nonstop3h 04m

$369

ChicagoVail

ORD - EGE

ORDEGE

Chicago O'Hare Intl

Fri 2/6

9:15 am-11:27 am

Nonstop3h 12m

$221

ChicagoVail

ORD - EGE

ORDEGE

Chicago O'Hare Intl

Thu 12/18

10:45 am-12:51 pm

Nonstop3h 06m

$221

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/29

Showing 1-10 of 19 results
1
2

Compare providers for flights from Chicago to Vail

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Chicago to Vail in October.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Chicago-Vail flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Chicago-Vail flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Chicago-Vail flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago-Vail flights, Cheapflights users trust eDreams the most. eDreams has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago-Vail flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

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 October 24, 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 30 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, March is the cheapest month in which you can book a flight from Chicago to Vail (average of $52). Flying from Chicago to Vail in July is currently the most expensive (average of $114). 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 October 30, 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 13% on your trip compared to booking a flight in the evening.

How much does it cost to fly round-trip from Chicago to Vail?

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 October 30, 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
8,998 reviews

Food

6.6

Comfort

7.3

Entertainment

7.1

Crew

8.1

Overall

7.4

Boarding

7.7

Reviews

1 / 20
10.0
Excellent

Julia,Sep 2025

BUF - DEN

The staff were amazing, from check in to boarding and on the flight. The range of entertainment options were really good as well.
United Airlines
7.4
Good
8,998 reviews
United Airlines
7.4
Good
8,998 reviews

Food

6.6

Comfort

7.3

Entertainment

7.1

Crew

8.1

Overall

7.4

Boarding

7.7

Reviews

1 / 20
10.0
Excellent

Julia,Sep 2025

BUF - DEN

The staff were amazing, from check in to boarding and on the flight. The range of entertainment options were really good as well.
American Airlines
7.2
Good
11,030 reviews
United Airlines
7.4
Good
8,998 reviews

Food

6.6

Comfort

7.3

Entertainment

7.1

Crew

8.1

Overall

7.4

Boarding

7.7

Reviews

1 / 20
10.0
Excellent

Julia,Sep 2025

BUF - DEN

The staff were amazing, from check in to boarding and on the flight. The range of entertainment options were really good as well.
Frontier
5.8
Fair
3,123 reviews
United Airlines
7.4
Good
8,998 reviews

Food

6.6

Comfort

7.3

Entertainment

7.1

Crew

8.1

Overall

7.4

Boarding

7.7

Reviews

1 / 20
10.0
Excellent

Julia,Sep 2025

BUF - DEN

The staff were amazing, from check in to boarding and on the flight. The range of entertainment options were really good as well.

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 3h 12m. 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 $289. Another option worth looking into is United Airlines, starting at $311 round trip. American Airlines is priced at 48% 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 $250. On average you can expect to pay $475. The most popular route, (Chicago O'Hare Intl - Vail Eagle County), can usually be booked for $340.

  • 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, March is the cheapest month in which you can book a flight from Chicago to Vail (average of $52). Flying from Chicago to Vail in July is currently the most expensive (average of $114). 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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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 October 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$289Average$478FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$311Average$573FlexibilityNo cancel feeOn-time69%

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