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Vail

$208+ 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 5/17. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — EGE
May 3 — May 101
Sun 5/3
Sun 5/10
1 adult, Economy
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Cheap 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 April 3, 2026.

This United Airlines deal was found by Cheapflights users on 3/29. 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.
Tue 6/26:00 am
ORD
-
EGE
1 stop7h 23m
United Airlines
Sun 6/78:00 am
EGE
-
ORD
Nonstop2h 40m
United Airlines
Deal found 3/29$389
This United Airlines deal was found by Cheapflights users on 3/31. 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.
Tue 4/212:35 pm
ORD
-
EGE
1 stop6h 47m
United Airlines
Tue 4/281:38 pm
EGE
-
ORD
1 stop5h 36m
United Airlines
Deal found 3/31$399
This United Airlines deal was found by Cheapflights users on 4/2. 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.
Fri 6/264:00 pm
ORD
-
EGE
Nonstop3h 05m
United Airlines
Mon 6/293:25 pm
EGE
-
ORD
1 stop6h 24m
United Airlines
Deal found 4/2$417
This United Airlines deal was found by Cheapflights users on 3/30. 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.
Mon 4/277:00 am
ORD
-
EGE
1 stop6h 28m
United Airlines
Mon 5/41:45 pm
EGE
-
ORD
1 stop6h 38m
United Airlines
Deal found 3/30$421
This American Airlines deal was found by Cheapflights users on 4/2. 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.
Fri 6/58:19 am
ORD
-
EGE
1 stop6h 12m
American Airlines
Mon 6/82:12 pm
EGE
-
ORD
1 stop6h 00m
American Airlines
Deal found 4/2$424
This American Airlines deal was found by Cheapflights users on 4/3. 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.
Fri 8/216:00 am
ORD
-
EGE
1 stop8h 36m
American Airlines
Fri 8/287:50 am
EGE
-
ORD
1 stop7h 10m
American Airlines
Deal found 4/3$432
This American Airlines deal was found by Cheapflights users on 3/31. 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.
Fri 4/1711:43 am
ORD
-
EGE
1 stop8h 26m
American Airlines
Fri 4/248:00 am
EGE
-
ORD
1 stop8h 44m
American Airlines
Deal found 3/31$439
This American Airlines deal was found by Cheapflights users on 3/31. 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 6/41:25 pm
ORD
-
EGE
1 stop6h 39m
American Airlines
Sun 6/72:12 pm
EGE
-
ORD
1 stop8h 25m
American Airlines
Deal found 3/31$444
This American Airlines deal was found by Cheapflights users on 4/2. 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.
Sat 4/1111:43 am
ORD
-
EGE
1 stop8h 26m
American Airlines
Sat 4/258:00 am
EGE
-
ORD
1 stop6h 18m
American Airlines
Deal found 4/2$449
This United Airlines deal was found by Cheapflights users on 4/2. 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 8/237:00 am
ORD
-
EGE
1 stop6h 21m
United Airlines
Thu 9/33:21 pm
EGE
-
ORD
1 stop5h 21m
United Airlines
Deal found 4/2$456

Find 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 April 3, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$389
(United Airlines)

One-way from

$208
(American Airlines)

Popular in

October

Cheapest in

January

Average price

$398

Good round-trip deal

$344 or less

Good one-way deal

$284 or less
Provider with most accurate pricing for Chicago (CHI)-Vail Eagle County flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Vail Eagle County flights.
Search Deals
From Chicago (CHI) to Vail Eagle County
Search Deals
One-way flight from Chicago (CHI) to Vail Eagle County
Search Deals
Highest demand for flights based on searches. 14% potential increase in price ($82 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($16 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 2026
Search Deals
Price to beat on a round-trip flight from Chicago (CHI) to Vail Eagle County.
Search Deals
Price to beat on a one-way flight from Chicago (CHI) to Vail Eagle County.
Search Deals

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 April 3, 2026.
Use the filters below to find and compare flights from Chicago to Vail that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoVail

ORD - EGE

ORDEGE

Chicago O'Hare Intl

Tue 6/2

6:00 am-12:23 pm

1 stop7h 23m

Vail Eagle County

Sun 6/7

8:00 am-11:40 am

Nonstop2h 40m

$389

ChicagoVail

ORD - EGE

ORDEGE

Chicago O'Hare Intl

Thu 4/16

2:35 pm-8:25 pm

1 stop6h 50m

Vail Eagle County

Mon 4/20

3:15 pm-11:28 pm

1 stop7h 13m

$399

ChicagoVail

ORD - EGE

ORDEGE

Chicago O'Hare Intl

Tue 5/5

10:49 am-2:32 pm

1 stop4h 43m

Vail Eagle County

Wed 5/13

1:45 pm-9:23 pm

1 stop6h 38m

$399

ChicagoVail

ORD - EGE

ORDEGE

Chicago O'Hare Intl

Fri 6/26

4:00 pm-6:05 pm

Nonstop3h 05m

Vail Eagle County

Mon 6/29

3:25 pm-10:49 pm

1 stop6h 24m

$417

ChicagoVail

ORD - EGE

ORDEGE

Chicago O'Hare Intl

Thu 6/18

5:00 am-9:53 am

1 stop5h 53m

Vail Eagle County

Mon 6/22

2:12 pm-9:12 pm

1 stop6h 00m

$444

ChicagoVail

ORD - EGE

ORDEGE

Chicago O'Hare Intl

Fri 5/22

1:25 pm-7:04 pm

1 stop6h 39m

Vail Eagle County

Mon 5/25

2:12 pm-11:37 pm

1 stop8h 25m

$479

ChicagoVail

ORD - EGE

ORDEGE

Chicago O'Hare Intl

Mon 4/20

2:05 pm-8:25 pm

1 stop7h 20m

Vail Eagle County

Sun 4/26

3:15 pm-10:54 pm

1 stop6h 39m

$489

ChicagoVail

ORD - EGE

ORDEGE

Chicago O'Hare Intl

Tue 4/7

2:35 pm-8:22 pm

1 stop6h 47m

Vail Eagle County

Wed 4/8

1:38 pm-8:14 pm

1 stop5h 36m

$491

ChicagoVail

ORD - EGE

ORDEGE

Chicago O'Hare Intl

Mon 4/27

8:40 am-12:28 pm

1 stop4h 48m

Vail Eagle County

Fri 5/1

1:45 pm-9:23 pm

1 stop6h 38m

$493
Quickest round-trip

ChicagoVail

ORD - EGE

ORDEGE

Chicago O'Hare Intl

Thu 6/4

10:54 am-2:23 pm

1 stop4h 29m

Vail Eagle County

Sun 6/7

8:00 am-11:40 am

Nonstop2h 40m

$529

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/1

Showing 1-10 of 22 resultsSorted by cheapest first
1
2
3

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 April.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice 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 FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-Vail flight deals on Cheapflights vs. FlightHub >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 FlightHub the most. FlightHub 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

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

Currently, November is the cheapest month in which you can book a flight from Chicago to Vail (average of $77). Flying from Chicago to Vail in July is currently the most expensive (average of $116). 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 April 3, 2026.

When flying from Chicago to Vail, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

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 April 3, 2026.
Get a feel of what it's like to fly with United Airlines and American Airlines 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
9,538 reviews

Crew

8.1

Overall

7.4

Food

6.6

Boarding

7.7

Comfort

7.3

Entertainment

7.1

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
9,538 reviews
United Airlines
7.4
Good
9,538 reviews

Crew

8.1

Overall

7.4

Food

6.6

Boarding

7.7

Comfort

7.3

Entertainment

7.1

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
7.1
Good
11,550 reviews
United Airlines
7.4
Good
9,538 reviews

Crew

8.1

Overall

7.4

Food

6.6

Boarding

7.7

Comfort

7.3

Entertainment

7.1

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 2 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 5h 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 $259. Another option worth looking into is United Airlines, starting at $287 round trip. American Airlines is priced at 46% 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 $158. On average you can expect to pay $368. The most popular route, (Chicago O'Hare Intl - Vail Eagle County), can usually be booked for $399.

  • 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, November is the cheapest month in which you can book a flight from Chicago to Vail (average of $77). Flying from Chicago to Vail in July is currently the most expensive (average of $116). 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
Beaver Creek
Eagle
Avon
Rifle

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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 April 3, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$259Average$421FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$287Average$465FlexibilityNo cancel feeOn-time69%

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