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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 3/2. Fares are subject to change and may not be available on all flights or dates of travel.
EGE — CHI
Feb 28 — Mar 71
Sat 2/28
Sat 3/7
1 adult, Economy
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Cheap 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 January 29, 2026.

This United Airlines deal was found by Cheapflights users on 1/26. 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 3/512:27 pm
EGE
-
ORD
Nonstop2h 53m
United Airlines
Sun 3/87:40 pm
ORD
-
EGE
Nonstop3h 07m
United Airlines
Deal found 1/26$331
This United Airlines deal was found by Cheapflights users on 1/27. 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 3/266:11 pm
EGE
-
ORD
1 stop4h 41m
United Airlines
Sun 3/297:00 am
ORD
-
EGE
1 stop6h 28m
United Airlines
Deal found 1/27$401
This United Airlines deal was found by Cheapflights users on 1/28. 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.
Thu 4/97:05 am
EGE
-
ORD
1 stop6h 47m
United Airlines
Sun 4/127:00 am
ORD
-
EGE
1 stop6h 28m
United Airlines
Deal found 1/28$427
This American Airlines deal was found by Cheapflights users on 1/28. 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 2/1210:48 am
EGE
-
ORD
Nonstop2h 47m
American Airlines
Mon 2/168:05 am
ORD
-
EGE
Nonstop3h 01m
American Airlines
Deal found 1/28$431
This United Airlines deal was found by Cheapflights users on 1/28. 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.
Wed 2/118:30 am
EGE
-
ORD
Nonstop3h 04m
United Airlines
Sat 2/147:40 pm
ORD
-
EGE
Nonstop3h 07m
United Airlines
Deal found 1/28$435
This United Airlines deal was found by Cheapflights users on 1/28. 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.
Thu 2/128:00 am
EGE
-
ORD
Nonstop3h 00m
United Airlines
Mon 2/162:02 pm
ORD
-
EGE
1 stop7h 10m
United Airlines
Deal found 1/28$441
This American Airlines deal was found by Cheapflights users on 1/28. 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 6/42:14 pm
EGE
-
ORD
1 stop6h 45m
American Airlines
Mon 6/86:00 am
ORD
-
EGE
1 stop8h 34m
American Airlines
Deal found 1/28$451
This Delta deal was found by Cheapflights users on 1/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/303:10 pm
EGE
-
MDW
1 stop6h 12m
Delta
Mon 2/26:00 am
MDW
-
EGE
1 stop9h 05m
Delta
Deal found 1/29$551
This Delta deal was found by Cheapflights users on 1/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/313:16 pm
EGE
-
MDW
1 stop6h 06m
Delta
Mon 2/26:00 am
MDW
-
EGE
1 stop9h 05m
Delta
Deal found 1/28$610
This Delta deal was found by Cheapflights users on 1/26. 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.
Thu 3/53:10 pm
EGE
-
MDW
1 stop6h 21m
Delta
Sun 3/86:00 am
MDW
-
EGE
1 stop9h 11m
Delta
Deal found 1/26$675
This Delta deal was found by Cheapflights users on 1/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/303:10 pm
EGE
-
MDW
1 stop6h 12m
Delta
Sun 2/16:00 am
MDW
-
EGE
1 stop9h 05m
Delta
Deal found 1/29$775
This Delta deal was found by Cheapflights users on 1/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/313:16 pm
EGE
-
MDW
1 stop6h 06m
Delta
Sun 2/16:00 am
MDW
-
EGE
1 stop9h 05m
Delta
Deal found 1/28$834

Find 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 January 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$331
(United Airlines)

One-way from

$221
(American Airlines)

Popular in

March

Cheapest in

October

Average price

$371

Good round-trip deal

$338 or less

Good one-way deal

$306 or less
Provider with most accurate pricing for Vail Eagle County-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Vail Eagle County-Chicago (CHI) flights.
Search Deals
From Vail Eagle County to Chicago (CHI)
Search Deals
One-way flight from Vail Eagle County to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 19% potential increase in price ($106 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 8% potential price decrease ($35 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals
Price to beat on a round-trip flight from Vail Eagle County to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Vail Eagle County to Chicago (CHI).
Search Deals

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 January 29, 2026.
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 3/5

12:27 pm-4:20 pm

Nonstop2h 53m

Chicago O'Hare Intl

Sun 3/8

7:40 pm-9:47 pm

Nonstop3h 07m

$331

VailChicago

EGE - ORD

EGEORD

Vail Eagle County

Thu 3/26

8:00 am-12:00 pm

Nonstop3h 00m

Chicago O'Hare Intl

Sun 3/29

9:10 am-11:16 am

Nonstop3h 06m

$331

VailChicago

EGE - ORD

EGEORD

Vail Eagle County

Thu 4/9

7:05 am-2:52 pm

1 stop6h 47m

Chicago O'Hare Intl

Sun 4/12

7:00 am-12:28 pm

1 stop6h 28m

$427

VailChicago

EGE - ORD

EGEORD

Vail Eagle County

Thu 2/12

8:00 am-12:00 pm

Nonstop3h 00m

Chicago O'Hare Intl

Mon 2/16

2:02 pm-8:12 pm

1 stop7h 10m

$441

VailChicago

EGE - ORD

EGEORD

Vail Eagle County

Thu 6/4

2:14 pm-9:59 pm

1 stop6h 45m

Chicago O'Hare Intl

Mon 6/8

1:25 pm-6:52 pm

1 stop6h 27m

$451

VailChicago

EGE - ORD

EGEORD

Vail Eagle County

Tue 4/21

1:38 pm-9:17 pm

1 stop6h 39m

Chicago O'Hare Intl

Sat 4/25

2:10 pm-8:22 pm

1 stop7h 12m

$460

VailChicago

EGE - MDW

EGEMDW

Vail Eagle County

Thu 3/5

3:10 pm-10:31 pm

1 stop6h 21m

Chicago Midway

Sun 3/8

6:00 am-2:11 pm

1 stop9h 11m

$675

VailChicago

EGE - MDW

EGEMDW

Vail Eagle County

Thu 3/26

3:31 pm-10:31 pm

1 stop6h 00m

Chicago Midway

Sun 3/29

6:00 am-2:11 pm

1 stop9h 11m

$969

VailChicago

EGE - MDW

EGEMDW

Vail Eagle County

Wed 2/11

3:10 pm-10:22 pm

1 stop6h 12m

Chicago Midway

Sun 2/15

6:00 am-2:05 pm

1 stop9h 05m

$2,000

VailChicago

EGE - MDW

EGEMDW

Vail Eagle County

Wed 2/11

3:10 pm-10:22 pm

1 stop6h 12m

Chicago Midway

Sat 2/14

6:00 am-2:05 pm

1 stop9h 05m

$2,020

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/28

Showing 1-10 of 27 results
1
2
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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 January.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*3 stars
ExpediaPrice Accuracy1 starTrust 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 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 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 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, February is the cheapest month in which you can book a flight from Vail to Chicago (average of $60). Flying from Vail to Chicago in June is currently the most expensive (average of $125). 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 January 29, 2026.

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

Weekly flight availability from Vail to Chicago

Explore weekly flight availability from Vail to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated January 29, 2026.

The most flights from EGE to CHI are scheduled on a Monday (4 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (1 on average).

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 January 29, 2026.
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
9,214 reviews

Comfort

7.3

Overall

7.4

Boarding

7.7

Crew

8.1

Food

6.6

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Michelle,Dec 2025

DEN - MKE

I liked that the plane waited 5 minutes for a family whose incoming plane was late. This was the last flight of the day to MKE. Flight attendants actually checked in throughout the flight. Although, not really friendly. Happy to see screens on seat backs again. This is my first time not flying first class in over 10 years. It was economy plus.
United Airlines
7.4
Good
9,214 reviews
United Airlines
7.4
Good
9,214 reviews

Comfort

7.3

Overall

7.4

Boarding

7.7

Crew

8.1

Food

6.6

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Michelle,Dec 2025

DEN - MKE

I liked that the plane waited 5 minutes for a family whose incoming plane was late. This was the last flight of the day to MKE. Flight attendants actually checked in throughout the flight. Although, not really friendly. Happy to see screens on seat backs again. This is my first time not flying first class in over 10 years. It was economy plus.
American Airlines
7.2
Good
11,205 reviews
United Airlines
7.4
Good
9,214 reviews

Comfort

7.3

Overall

7.4

Boarding

7.7

Crew

8.1

Food

6.6

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Michelle,Dec 2025

DEN - MKE

I liked that the plane waited 5 minutes for a family whose incoming plane was late. This was the last flight of the day to MKE. Flight attendants actually checked in throughout the flight. Although, not really friendly. Happy to see screens on seat backs again. This is my first time not flying first class in over 10 years. It was economy plus.

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 2 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 2h 53m. 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 $331. Users have found that United Airlines is 57% cheaper than the other options available to this destination.

  • What are the most reliable airlines from Vail to Chicago?

    Consider United Airlines (72%), American Airlines (63%) or Qatar Airways (63%) when booking your flight. These represent the most reliable airlines when flying from Vail to Chicago.

  • What are the cheapest flights from Vail to Chicago?

    Looking at all options, your cheapest flight can be booked for $214. While the most popular route (Vail Eagle County - Chicago O'Hare Intl) can be booked for $331 on average, our data indicates $469 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, February is the cheapest month in which you can book a flight from Vail to Chicago (average of $60). Flying from Vail to Chicago in June is currently the most expensive (average of $125). 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
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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Alternative routes for Vail to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
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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 January 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$191Average$486FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$331Average$476FlexibilityNo cancel feeOn-time71%

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