HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chicago

$275+ 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 7/22. Fares are subject to change and may not be available on all flights or dates of travel.
EGE — CHI
Jul 8 — Jul 151
Tue 7/8
Tue 7/15
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 July 3, 2025.

Round-trip from

$309
(United Airlines)

One-way from

$275
(United Airlines)

Popular in

May

Cheapest in

September

Average price

$205

Good round-trip deal

$549 or less

Good one-way deal

$273 or less
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. 12% potential increase in price ($27 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2025
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 July 3, 2025.

This United Airlines deal was found by Cheapflights users on 7/2. 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.
Thu 12/41:30 pmEGE - ORD
1 stop6h 28mUnited Airlines
Mon 12/82:30 pmORD - EGE
1 stop6h 29mUnited Airlines
Deal found 7/2$309
This American Airlines deal was found by Cheapflights users on 7/3. 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.
Tue 7/228:15 amEGE - ORD
1 stop8h 05mAmerican Airlines
Sat 7/265:00 amORD - EGE
1 stop5h 42mAmerican Airlines
Deal found 7/3$324

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 July 3, 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 12/4

1:30 pm-8:58 pm

1 stop6h 28m

Chicago O'Hare Intl

Mon 12/8

2:30 pm-7:59 pm

1 stop6h 29m

$309

VailChicago

EGE - ORD

EGEORD

Vail Eagle County

Tue 7/22

8:15 am-5:20 pm

1 stop8h 05m

Chicago O'Hare Intl

Sat 7/26

5:00 am-9:42 am

1 stop5h 42m

$324

VailChicago

EGE - ORD

EGEORD

Vail Eagle County

Tue 7/22

7:25 am-3:05 pm

1 stop6h 40m

$275

VailChicago

EGE - ORD

EGEORD

Vail Eagle County

Fri 8/8

8:15 am-5:10 pm

1 stop7h 55m

$315

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/1

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 July 3, 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.

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 July 3, 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
8,861 reviews

Boarding

7.7

Entertainment

7.0

Comfort

7.3

Food

6.6

Overall

7.4

Crew

8.1

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
8,861 reviews
United Airlines
7.4
Good
8,861 reviews

Boarding

7.7

Entertainment

7.0

Comfort

7.3

Food

6.6

Overall

7.4

Crew

8.1

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
8,861 reviews

Boarding

7.7

Entertainment

7.0

Comfort

7.3

Food

6.6

Overall

7.4

Crew

8.1

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.

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

    Currently priced at $309, 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 $324.

  • What are the cheapest flights from Vail to Chicago?

    Looking at all options, your cheapest flight can be booked for $249. While the most popular route (Vail Eagle County - Chicago O'Hare Intl) can be booked for $309 on average our data indicates $458 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 Vail?

Book flights to Vail if you plan to visit one of these locations
Merrillville
Lansing
Benton Harbor
Porter
Hammond
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
Denver to Moline flights
Durango to O'Hare Intl flights
Grand Junction to O'Hare Intl flights
Denver to Peoria flights
Aspen to O'Hare Intl flights
Denver to Bloomington flights
Colorado Springs to St. Louis flights
Colorado Springs to Midway flights
Montrose to O'Hare Intl flights
Denver to Evansville flights
Durango to St. Louis flights
Vail to O'Hare Intl flights
Grand Junction to Midway flights
Denver to Rockford flights
Denver to Springfield flights
Montrose to St. Louis flights
Gunnison to O'Hare Intl flights
Hayden to O'Hare Intl flights
Colorado Springs to Peoria flights
Montrose to Midway flights
Aspen to St. Louis flights
Aspen to Midway flights
Hayden to St. Louis flights
Colorado Springs to Moline flights
Vail to St. Louis flights
Denver to Dubuque flights
Grand Junction to Peoria flights
Grand Junction to Bloomington flights
Colorado Springs to Evansville flights
Grand Junction to St. Louis flights
Montrose to Peoria flights
Denver to Champaign flights
Colorado Springs to Springfield flights
Denver to Decatur flights
Montrose to Springfield flights
Colorado Springs to Champaign flights
Hayden to Moline flights
Colorado Springs to Bloomington flights
Gunnison to St. Louis flights
Durango to Moline flights
Durango to Midway flights
Vail to Midway 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 July 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$348Average$549FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$359Average$484FlexibilityNo cancel feeOn-time71%

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.