HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chicago

$125+ 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 4/7. Fares are subject to change and may not be available on all flights or dates of travel.
EGE — CHI
Apr 2 — Apr 91
Wed 4/2
Wed 4/9
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Vail to Chicago with Cheapflights

1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”
2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.
3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 March 28, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$429
(American Airlines)

One-way from

$125
(Frontier)

Good round-trip deal

$387 or less

Good one-way deal

$318 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
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

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 March 28, 2025.

This Frontier deal was found by Cheapflights users on 3/26. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/102:58 pmEGE - ORD
1 stop8h 12mFrontier
Mon 4/145:01 amORD - EGE
1 stop6h 57mFrontier
Deal found 3/26$238
This United Airlines deal was found by Cheapflights users on 3/25. 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 4/231:45 pmEGE - ORD
1 stop6h 35mUnited Airlines
Wed 4/307:10 amORD - EGE
1 stop6h 31mUnited Airlines
Deal found 3/25$349
This American Airlines deal was found by Cheapflights users on 3/26. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/178:00 amEGE - ORD
2 stops11h 50mAmerican Airlines
Sun 5/251:58 pmORD - EGE
1 stop5h 54mAmerican Airlines
Deal found 3/26$392

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 March 28, 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 4/10

2:58 pm-12:10 am

1 stop8h 12m

Chicago O'Hare Intl

Mon 4/14

5:01 am-10:58 am

1 stop6h 57m

$238

VailChicago

EGE - ORD

EGEORD

Vail Eagle County

Wed 4/23

1:45 pm-9:20 pm

1 stop6h 35m

Chicago O'Hare Intl

Wed 4/30

7:10 am-12:41 pm

1 stop6h 31m

$349

VailChicago

EGE - ORD

EGEORD

Vail Eagle County

Sat 5/17

8:00 am-8:50 pm

2 stops11h 50m

Chicago O'Hare Intl

Sun 5/25

1:58 pm-6:52 pm

1 stop5h 54m

$392

VailChicago

EGE - ORD

EGEORD

Vail Eagle County

Thu 4/17

2:58 pm-12:10 am

1 stop8h 12m

$125

VailChicago

EGE - MDW

EGEMDW

Vail Eagle County

Mon 4/7

11:48 am-10:41 pm

1 stop9h 53m

$125

VailChicago

EGE - ORD

EGEORD

Vail Eagle County

Wed 4/23

3:20 pm-7:37 am

2 stops15h 17m

$276

VailChicago

EGE - ORD

EGEORD

Vail Eagle County

Fri 8/8

2:39 pm-11:34 pm

1 stop7h 55m

$335

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/26

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 March.
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 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, 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 $323). 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 March 28, 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 6% on your trip compared to booking a flight at noon.

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 March 28, 2025.
United Airlines
7.4
Good
8,603 reviews

Comfort

7.3

Crew

8.1

Food

6.6

Boarding

7.7

Entertainment

7.0

Overall

7.4

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
8,603 reviews
United Airlines
7.4
Good
8,603 reviews

Comfort

7.3

Crew

8.1

Food

6.6

Boarding

7.7

Entertainment

7.0

Overall

7.4

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
8,603 reviews

Comfort

7.3

Crew

8.1

Food

6.6

Boarding

7.7

Entertainment

7.0

Overall

7.4

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!
Frontier
6.0
Okay
3,271 reviews
United Airlines
7.4
Good
8,603 reviews

Comfort

7.3

Crew

8.1

Food

6.6

Boarding

7.7

Entertainment

7.0

Overall

7.4

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 1 outbound flight to Chicago per day from 2 airlines. Vail Eagle County is conveniently located just 28.9 mi from Vail’s city center.

  • What are the cheapest airlines flying from Vail to Chicago round-trip?

    Currently priced at $429, American Airlines will fly you from Vail to Chicago and back. In addition to American Airlines, many other airlines offer competitively priced options for your trip. Check Cheapflights for deals on United Airlines for as low as $459.

  • What are the cheapest airlines to fly from Vail to Chicago one-way?

    $125 is the cheapest one-way deal found within the past few days, from Frontier. You may also be able to find cheap deals on American Airlines and United Airlines, with prices starting from $335 and $414, respectively.

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

    Consider Qatar Airways (86%), American Airlines (74%) or United Airlines (66%) 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 $196. While the most popular route (Vail Eagle County - Chicago O'Hare Intl) can be booked for $418 on average our data indicates $1,062 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 $323). 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
Merrillville
New Buffalo
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Vail to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
Denver to O'Hare Intl flights
Denver to Midway flights
Denver to St. Louis flights
Colorado Springs to O'Hare Intl flights
Colorado Springs to Midway flights
Denver to Moline flights
Durango to O'Hare Intl flights
Aspen to O'Hare Intl flights
Denver to Peoria flights
Vail to O'Hare Intl flights
Grand Junction to O'Hare Intl flights
Montrose to O'Hare Intl flights
Colorado Springs to St. Louis flights
Denver to Bloomington flights
Montrose to St. Louis flights
Grand Junction to St. Louis flights
Grand Junction to Midway flights
Denver to Decatur flights
Gunnison to O'Hare Intl flights
Montrose to Midway flights
Hayden to O'Hare Intl flights
Denver to Evansville flights
Denver to Champaign flights
Aspen to Midway flights
Hayden to St. Louis flights
Denver to Rockford flights
Colorado Springs to Moline flights
Denver to Dubuque flights
Denver to Springfield flights
Colorado Springs to Peoria flights
Grand Junction to Peoria flights
Colorado Springs to Springfield flights
Durango to St. Louis flights
Hayden to Moline flights
Gunnison to St. Louis flights
Colorado Springs to Evansville flights
Montrose to Springfield flights
Durango to Moline flights
Colorado Springs to Bloomington flights
Grand Junction to Bloomington flights
Vail to St. Louis flights
Vail to Midway flights
Durango to Midway flights
Aspen to St. Louis flights
Montrose to Peoria flights
Colorado Springs to Champaign flights

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 March 28, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$359Average$501FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$368Average$529FlexibilityNo cancel feeOn-time69%
100% Free
Cheapflights is completely free to use, so you can start saving the moment you arrive.
Book with Flexibility
Our users can plan ahead with confidence and find flights with no change fees
Travel Smart
Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.