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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 3/16. Fares are subject to change and may not be available on all flights or dates of travel.
EGE — CHI
Oct 17 — Oct 241
Fri 10/17
Fri 10/24
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 September 17, 2025.

Round-trip from

$269
(United Airlines)

One-way from

$221
(American Airlines)

Popular in

March

Cheapest in

January

Average price

$422

Good round-trip deal

$343 or less

Good one-way deal

$210 or less
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 ($191 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 September 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 September 17, 2025.

This American Airlines deal was found by Cheapflights users on 9/17. 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.
Thu 11/138:00 amEGE - ORD
1 stop6h 28mAmerican Airlines
Sun 11/1611:46 amORD - EGE
1 stop8h 25mAmerican Airlines
Deal found 9/17$309
This United Airlines deal was found by Cheapflights users on 9/14. 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 10/141:40 pmEGE - ORD
1 stop5h 45mUnited Airlines
Sat 10/182:53 pmORD - EGE
1 stop6h 15mUnited Airlines
Deal found 9/14$317
This United Airlines deal was found by Cheapflights users on 9/15. 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.
Wed 10/153:20 pmEGE - ORD
1 stop7h 39mUnited Airlines
Wed 10/227:10 amORD - EGE
1 stop6h 28mUnited Airlines
Deal found 9/15$328
This United Airlines deal was found by Cheapflights users on 9/16. 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 11/141:30 pmEGE - ORD
1 stop5h 10mUnited Airlines
Sun 11/167:10 amORD - EGE
1 stop6h 14mUnited Airlines
Deal found 9/16$349
This United Airlines deal was found by Cheapflights users on 9/14. 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 10/133:20 pmEGE - ORD
1 stop7h 39mUnited Airlines
Sat 10/182:53 pmORD - EGE
1 stop6h 15mUnited Airlines
Deal found 9/14$374
This United Airlines deal was found by Cheapflights users on 9/17. 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.
Sat 10/181:30 pmEGE - ORD
1 stop5h 25mUnited Airlines
Mon 10/202:53 pmORD - EGE
1 stop6h 15mUnited Airlines
Deal found 9/17$409
This United Airlines deal was found by Cheapflights users on 9/17. 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.
Thu 11/131:30 pmEGE - ORD
1 stop5h 10mUnited Airlines
Sun 11/166:10 pmORD - EGE
2 stops19h 14mUnited Airlines
Deal found 9/17$425
This United Airlines deal was found by Cheapflights users on 9/15. 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 10/161:40 pmEGE - ORD
1 stop5h 15mUnited Airlines
Sun 10/197:10 amORD - EGE
1 stop6h 28mUnited Airlines
Deal found 9/15$432
This United Airlines deal was found by Cheapflights users on 9/15. 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 10/171:40 pmEGE - ORD
1 stop5h 45mUnited Airlines
Sun 10/195:01 amORD - EGE
1 stop10h 31mUnited Airlines
Deal found 9/15$447

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 September 17, 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

Thu 11/13

8:00 am-3:28 pm

1 stop6h 28m

Chicago O'Hare Intl

Sun 11/16

11:46 am-7:11 pm

1 stop8h 25m

$309

VailChicago

EGE - ORD

EGEORD

Vail Eagle County

Tue 10/14

1:40 pm-8:25 pm

1 stop5h 45m

Chicago O'Hare Intl

Sat 10/18

2:53 pm-8:08 pm

1 stop6h 15m

$317

VailChicago

EGE - ORD

EGEORD

Vail Eagle County

Wed 10/15

3:20 pm-11:59 pm

1 stop7h 39m

Chicago O'Hare Intl

Wed 10/22

7:10 am-12:38 pm

1 stop6h 28m

$328

VailChicago

EGE - ORD

EGEORD

Vail Eagle County

Fri 11/14

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

$349

VailChicago

EGE - ORD

EGEORD

Vail Eagle County

Mon 10/13

3:20 pm-11:59 pm

1 stop7h 39m

Chicago O'Hare Intl

Sat 10/18

2:53 pm-8:08 pm

1 stop6h 15m

$374

VailChicago

EGE - ORD

EGEORD

Vail Eagle County

Sat 10/18

1:30 pm-9:30 pm

1 stop7h 00m

Chicago O'Hare Intl

Mon 10/20

2:53 pm-8:08 pm

1 stop6h 15m

$409

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

$619

VailChicago

EGE - MDW

EGEMDW

Vail Eagle County

Thu 3/5

2:56 pm-9:46 pm

1 stop5h 50m

Chicago Midway

Sun 3/8

6:00 am-1:55 pm

1 stop8h 55m

$788

VailChicago

EGE - ORD

EGEORD

Vail Eagle County

Mon 3/16

10:34 am-2:34 pm

Nonstop3h 00m

$221

VailChicago

EGE - ORD

EGEORD

Vail Eagle County

Tue 12/9

8:00 am-3:19 pm

1 stop6h 19m

$231

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/16

Showing 1-10 of 21 results
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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, August is the cheapest month in which you can book a flight from Vail to Chicago (average of $245). Flying from Vail to Chicago in March is currently the most expensive (average of $321). 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 EGE to CHI?

Find hourly flight availability from Vail to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 17, 2025.

A simple way to save on the total cost of your ticket is to fly from Vail to Chicago in the morning. If you’re flexible enough to do this you can expect to save up to 9% on your trip compared to booking a flight at noon.

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

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 September 17, 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
8,926 reviews

Entertainment

7.1

Comfort

7.3

Overall

7.4

Crew

8.1

Boarding

7.7

Food

6.6

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!
United Airlines
7.4
Good
8,926 reviews
United Airlines
7.4
Good
8,926 reviews

Entertainment

7.1

Comfort

7.3

Overall

7.4

Crew

8.1

Boarding

7.7

Food

6.6

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!
American Airlines
7.2
Good
10,000 reviews
United Airlines
7.4
Good
8,926 reviews

Entertainment

7.1

Comfort

7.3

Overall

7.4

Crew

8.1

Boarding

7.7

Food

6.6

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!

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 5h 45m. 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 $329, 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 26% 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 $209. While the most popular route (Vail Eagle County - Chicago O'Hare Intl) can be booked for $328 on average, our data indicates $534 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, August is the cheapest month in which you can book a flight from Vail to Chicago (average of $245). Flying from Vail to Chicago in March is currently the most expensive (average of $321). 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
Benton Harbor
Porter
Chesterton

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Alternative routes for Vail to Chicago

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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 September 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$329Average$519FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$359Average$484FlexibilityNo cancel feeOn-time71%

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