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$221+ Cheap flights from Vail (EGE) to Chicago (CHI)

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 12/21. Fares are subject to change and may not be available on all flights or dates of travel.
EGE — CHI
Dec 2 — Dec 91
Tue 12/2
Tue 12/9
1 adult, Economy
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Cheap flight deals from Vail to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Vail (EGE) to Chicago (CHI). 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 November 2, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

Expedia
3 stars

Round-trip from

$314
(United Airlines)

One-way from

$221
(American Airlines)

Popular in

March

Cheapest in

January

Average price

$193

Good round-trip deal

$398 or less

Good one-way deal

$345 or less
Provider with most accurate pricing for Vail Eagle County-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Vail Eagle County-Chicago (CHI) flights.
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From Vail Eagle County to Chicago (CHI)
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One-way flight from Vail Eagle County to Chicago (CHI)
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Highest demand for flights based on searches. 30% potential increase in price ($195 potential increase over avg. RT price).
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Cheapest flight prices on average. 13% potential price decrease ($53 potential savings vs. average RT price).
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Average for round-trip flights in November 2025
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Price to beat on a round-trip flight from Vail Eagle County to Chicago (CHI).
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Price to beat on a one-way flight from Vail Eagle County to Chicago (CHI).
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Find flight deals from Vail to Chicago

Cheapest flights from Vail to Chicago
Explore the most affordable flight options available from Vail to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 2, 2025.

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.
Thu 11/131:30 pmEGE - ORD
1 stop6h 28mUnited Airlines
Sun 11/167:10 amORD - EGE
1 stop6h 14mUnited Airlines
Deal found 10/30$314
This United Airlines deal was found by Cheapflights users on 11/1. 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 11/143:15 pmEGE - ORD
1 stop7h 44mUnited Airlines
Sun 11/167:10 amORD - EGE
1 stop6h 14mUnited Airlines
Deal found 11/1$363
This United Airlines deal was found by Cheapflights users on 11/2. 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.
Tue 12/308:25 amEGE - ORD
Nonstop3h 04mUnited Airlines
Wed 12/314:20 pmORD - EGE
Nonstop3h 01mUnited Airlines
Deal found 11/2$386
This United Airlines deal was found by Cheapflights users on 10/31. 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.
Fri 11/73:15 pmEGE - ORD
1 stop7h 44mUnited Airlines
Mon 11/108:47 amORD - EGE
1 stop4h 37mUnited Airlines
Deal found 10/31$413
This United Airlines deal was found by Cheapflights users on 11/1. 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 11/153:15 pmEGE - ORD
2 stops14h 15mUnited Airlines
Sun 11/168:47 amORD - EGE
1 stop4h 37mUnited Airlines
Deal found 11/1$444
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.
Sat 11/18:08 amEGE - ORD
1 stop5h 58mAmerican Airlines
Tue 11/41:23 pmORD - EGE
1 stop6h 48mAmerican Airlines
Deal found 10/30$529
This Delta deal was found by Cheapflights users on 11/2. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/3011:20 amEGE - MDW
1 stop4h 59mDelta
Wed 12/316:00 amMDW - EGE
1 stop9h 30mDelta
Deal found 11/2$859

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

Fly from

Vail

Fly to

Chicago

Route

Depart

Return

Price

VailChicago

EGE - ORD

EGEORD

Vail Eagle County

Fri 2/27

11:50 am-6:57 pm

1 stop6h 07m

Chicago O'Hare Intl

Mon 3/2

5:50 am-1:55 pm

1 stop9h 05m

$309

VailChicago

EGE - ORD

EGEORD

Vail Eagle County

Sat 11/15

3:15 pm-11:59 pm

1 stop7h 44m

Chicago O'Hare Intl

Sun 11/16

7:10 am-12:24 pm

1 stop6h 14m

$314

VailChicago

EGE - ORD

EGEORD

Vail Eagle County

Thu 11/13

1:30 pm-8:58 pm

1 stop6h 28m

Chicago O'Hare Intl

Sun 11/16

7:10 am-12:24 pm

1 stop6h 14m

$314

VailChicago

EGE - ORD

EGEORD

Vail Eagle County

Fri 11/14

1:30 pm-7:40 pm

1 stop5h 10m

Chicago O'Hare Intl

Sun 11/16

7:10 am-12:24 pm

1 stop6h 14m

$314

VailChicago

EGE - ORD

EGEORD

Vail Eagle County

Fri 2/27

11:18 am-7:40 pm

1 stop7h 22m

Chicago O'Hare Intl

Mon 3/2

7:35 pm-9:42 pm

Nonstop3h 07m

$379

VailChicago

EGE - ORD

EGEORD

Vail Eagle County

Tue 12/30

8:25 am-12:29 pm

Nonstop3h 04m

Chicago O'Hare Intl

Wed 12/31

4:20 pm-6:21 pm

Nonstop3h 01m

$386

VailChicago

EGE - ORD

EGEORD

Vail Eagle County

Fri 2/27

10:49 am-2:35 pm

Nonstop2h 46m

Chicago O'Hare Intl

Mon 3/2

8:05 am-10:09 am

Nonstop3h 04m

$390

VailChicago

EGE - MDW

EGEMDW

Vail Eagle County

Thu 3/5

2:56 pm-9:46 pm

1 stop5h 50m

Chicago Midway

Mon 3/9

6:00 am-1:55 pm

1 stop8h 55m

$519

VailChicago

EGE - MDW

EGEMDW

Vail Eagle County

Tue 12/30

11:20 am-5:19 pm

1 stop4h 59m

Chicago Midway

Wed 12/31

6:00 am-2:30 pm

1 stop9h 30m

$859

VailChicago

EGE - ORD

EGEORD

Vail Eagle County

Wed 12/31

12:01 pm-4:01 pm

Nonstop3h 00m

$221

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/1

Showing 1-10 of 19 results
1
2

Compare providers for flights from Vail to Chicago

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 Vail to Chicago in November.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star

*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 Vail-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Vail-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Vail-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Vail-Chicago flights, Cheapflights users trust Expedia the most. Expedia 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 Vail-Chicago 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 Vail to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Vail 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 Vail to Chicago

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

Currently, January is the cheapest month in which you can book a flight from Vail to Chicago (average of $58). Flying from Vail to Chicago in June is currently the most expensive (average of $122). 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.

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated November 2, 2025.
Read reviews from past customers who have flown United Airlines and American Airlines from Vail to Chicago. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
8,997 reviews

Food

6.6

Comfort

7.3

Crew

8.1

Entertainment

7.1

Boarding

7.7

Overall

7.4

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
United Airlines
7.4
Good
8,997 reviews
United Airlines
7.4
Good
8,997 reviews

Food

6.6

Comfort

7.3

Crew

8.1

Entertainment

7.1

Boarding

7.7

Overall

7.4

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
American Airlines
7.2
Good
11,034 reviews
United Airlines
7.4
Good
8,997 reviews

Food

6.6

Comfort

7.3

Crew

8.1

Entertainment

7.1

Boarding

7.7

Overall

7.4

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.

Related info for your journey

Find useful and relevant information for your journey from Vail to Chicago. 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 from for flights from Vail to Chicago?

    Most people fly from Vail Eagle County (EGE) if they book a flight from Vail to Chicago. On average, Eagle County has 0 outbound flights to Chicago per day from 2 airlines. Vail Eagle County is conveniently located just 28.9 mi from Vail’s city center.

  • How long is the flight from Vail to Chicago?

    Departing from Vail to Chicago will take you 6h 07m. The distance between Vail and Chicago 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 Vail to Chicago round-trip?

    Currently priced at $191, United Airlines will fly you from Vail to Chicago and back. In addition to United Airlines, many other airlines offer competitively priced options for your trip. Check Cheapflights for deals on American Airlines for as low as $359. Users have found that United Airlines is 56% cheaper than the other options available to this destination.

  • What are the cheapest flights from Vail to Chicago?

    Looking at all options, your cheapest flight can be booked for $139. While the most popular route (Vail Eagle County - Chicago O'Hare Intl) can be booked for $314 on average, our data indicates $621 when flying from Vail to Chicago.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Vail to Chicago 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 Vail to Chicago?

    Currently, January is the cheapest month in which you can book a flight from Vail to Chicago (average of $58). Flying from Vail to Chicago in June is currently the most expensive (average of $122). 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 Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Porter
Benton Harbor

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Top 2 airlines flying from Vail to Chicago

Discover the top 2 airlines that operate flights from Vail to Chicago. 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 November 2, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$191Average$508FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$359Average$478FlexibilityNo cancel feeOn-time71%

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