$110 Cheap Flights from Vail (EGE) to Chicago (ORD)

View $110 flight on Fri, Dec 19, 2025Opens in a new window

Popular airlines from Vail/Eagle Airport (EGE) to Chicago O'Hare Intl. Airport (ORD)

  • Plan, book, fly with confidence

  • trending down icon

    Be in the know

    Get alerts if flight prices drop or rise*
  • bex rewards loyalty icon

    Book smarter

    Save up to 30% on select hotels after you book a flight*
  • one key icon

    Earn twice

    Earn your airline miles on top of our OneKeyCash
    Learn about One Key

Cheap Flights from Vail to Chicago (EGE-ORD)

Prices were available within the past 7 days and start at $110 for one-way flights and $229 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

American Airlines
Thu, Feb 26 - Mon, Mar 2
EGE
Vail
ORD
Chicago
$229 Roundtrip, found 14 hours ago
$229
Roundtrip
found 14 hours ago
Select American Airlines flight, departing Thu, Feb 26 from Vail to Chicago, returning Mon, Mar 2, priced at $229 found 14 hours ago
American Airlines
Thu, Feb 26 - Mon, Mar 2
EGE
Vail
ORD
Chicago
$239 Roundtrip, found 14 hours ago
$239
Roundtrip
found 14 hours ago
Select American Airlines flight, departing Thu, Feb 26 from Vail to Chicago, returning Mon, Mar 2, priced at $239 found 14 hours ago
American Airlines
Fri, Jan 16 - Wed, Jan 21
EGE
Vail
ORD
Chicago
$249 Roundtrip, found 23 hours ago
$249
Roundtrip
found 23 hours ago
Select American Airlines flight, departing Fri, Jan 16 from Vail to Chicago, returning Wed, Jan 21, priced at $249 found 23 hours ago
United
Sat, Dec 27 - Wed, Dec 31
EGE
Vail
ORD
Chicago
$259 Roundtrip, found 18 hours ago
$259
Roundtrip
found 18 hours ago
Select United flight, departing Sat, Dec 27 from Vail to Chicago, returning Wed, Dec 31, priced at $259 found 18 hours ago
United
Fri, Jan 16 - Wed, Jan 21
EGE
Vail
ORD
Chicago
$268 Roundtrip, found 23 hours ago
$268
Roundtrip
found 23 hours ago
Select United flight, departing Fri, Jan 16 from Vail to Chicago, returning Wed, Jan 21, priced at $268 found 23 hours ago
American Airlines
Thu, Feb 26 - Mon, Mar 2
EGE
Vail
ORD
Chicago
$279 Roundtrip, found 14 hours ago
$279
Roundtrip
found 14 hours ago
Select American Airlines flight, departing Thu, Feb 26 from Vail to Chicago, returning Mon, Mar 2, priced at $279 found 14 hours ago
United
Fri, Jan 16 - Wed, Jan 21
EGE
Vail
ORD
Chicago
$287 Roundtrip, found 23 hours ago
$287
Roundtrip
found 23 hours ago
Select United flight, departing Fri, Jan 16 from Vail to Chicago, returning Wed, Jan 21, priced at $287 found 23 hours ago
United
Sat, Dec 27 - Wed, Dec 31
EGE
Vail
ORD
Chicago
$288 Roundtrip, found 18 hours ago
$288
Roundtrip
found 18 hours ago
Select United flight, departing Sat, Dec 27 from Vail to Chicago, returning Wed, Dec 31, priced at $288 found 18 hours ago
American Airlines
Thu, Feb 26 - Mon, Mar 2
EGE
Vail
ORD
Chicago
$289 Roundtrip, found 14 hours ago
$289
Roundtrip
found 14 hours ago
Select American Airlines flight, departing Thu, Feb 26 from Vail to Chicago, returning Mon, Mar 2, priced at $289 found 14 hours ago
Delta
Thu, Feb 26 - Mon, Mar 2
EGE
Vail
ORD
Chicago
$394 Roundtrip, found 14 hours ago
$394
Roundtrip
found 14 hours ago
Select Delta flight, departing Thu, Feb 26 from Vail to Chicago, returning Mon, Mar 2, priced at $394 found 14 hours ago

Find the cheapest month to fly from Vail (EGE) to Chicago (ORD)

March is typically the cheapest month to fly

From $93 - $793 per traveler.

Graph displaying average flight prices per month

Alternative airports near Chicago

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to O'Hare Intl. ORD. Cheapest option available. Average driving time to city center is 23 minutes. Flights from $748
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from $748
Flights from Vail (EGE) to Chicago (ORD)
Origin airport
Eagle County Regional
Destination airport
O'Hare Intl.
Airlines serving
American Airlines, Delta, United
Roundtrip price
$229
Distance
1004 mi

Vail to Chicago Flights

The cheapest times to fly from Vail to Chicago

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Vail to Chicago are during the month of February. You can find some of the cheapest flights from Vail to Chicago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Vail to Chicago

Sunday is one of the best days to book for cheap flights from Vail to Chicago: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Vail to Chicago

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Vail to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from $110 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Vail to Chicago flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Vail to Chicago airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Frequently asked questions

How much does a flight from Eagle County Regional Airport (EGE) to O'Hare Intl. Airport (ORD) cost?
You can score cheap return tickets from Eagle County Regional Airport (EGE) to O'Hare Intl. Airport (ORD) starting at $885. Book your seat and get ready for takeoff. This information is based on the cheapest price found on Expedia for this return journey departing within the next three months. This airfare is for a United flight leaving EGE on July 27 2025 and touching down at ORD. The price was last updated on July 23 2025 and has not changed since.
What is the cheapest month to fly from EGE to ORD?
The cheapest flights from EGE to ORD are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
Which airlines fly direct from Eagle County Regional Airport (EGE) to O'Hare Intl. Airport (ORD)?
Board a direct flight with United Airlines and go straight from Eagle County Regional Airport (EGE) to O'Hare Intl. Airport (ORD).
What is the cheapest airline that flies from EGE to ORD?
Jet off from EGE to ORD with United. This airline currently offers the lowest one-way fare for this route, starting at $580. This fare is based on the lowest price found on Expedia departing within the next three months. The flight takes off from EGE on July 27 2025. Prices were last updated on July 23 2025 and have not changed since.
How many flights per day from Eagle County Regional Airport (EGE) to O'Hare Intl. Airport (ORD)?
Every day, an average of 2 direct flights operate from Eagle County Regional Airport (EGE) to O'Hare Intl. Airport (ORD). Choose the departure date that fits your schedule best.
What are the most popular departure times for flights from Eagle County Regional Airport (EGE) to O'Hare Intl. Airport (ORD)?
The 12 PM departures from EGE to ORD are the busiest. Prices can be higher for these popular slots. If you're looking to save, pick a less crowded time to fly.
What day of the week has the most flights from EGE to ORD?
Friday offers the most flights from Eagle County Regional Airport (EGE) to O'Hare Intl. Airport (ORD). Consider leaving on this day and you'll have the best chance of finding a departure that fits your itinerary.
What is the earliest flight from Eagle County Regional Airport (EGE) to O'Hare Intl. Airport (ORD)?
Catch the earliest flight at around 8:45AM UTC-7, leaving from Eagle County Regional Airport (EGE). You'll be in the air for around 2h 54m, reaching O'Hare Intl. Airport (ORD) at approximately 12:39PM UTC-6.
How long does it take to fly from Eagle County Regional Airport (EGE) to O'Hare Intl. Airport (ORD)?
Flights from EGE to ORD have an average travel time of 2 hours and 53 minutes. The total distance between these two airports is 1,000 mi.
What is the best time to fly from Eagle County Regional Airport (EGE) to O'Hare Intl. Airport (ORD)?
To land at O'Hare Intl. Airport (ORD) on schedule, book a flight that takes off from Eagle County Regional Airport (EGE) before 3 PM. The chance of cancellations is 22% higher, on average, for departures after this time.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
What airports do you fly into for Chicago from Eagle County Regional Airport (EGE)?
Check out your flight options from Eagle County Regional Airport (EGE) to O'Hare Intl. Airport (ORD). This is the only Chicago airport you can jet into if you're taking a direct flight.
Is it cheaper to buy a plane ticket from Eagle County Regional Airport (EGE) to O'Hare Intl. Airport (ORD) last-minute?
Last-minute fares from EGE to ORD are typically more expensive. To lock in the best rates, start looking for flights well ahead of time. That said, if you're flexible with your travel dates, you may score a cheap fare just before your departure.
Is it cheaper to book an EGE to ORD flight and hotel package?
Securing an EGE to ORD flight and hotel package is generally cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your travels all in one place. Pick from our extensive range of stays and then add car rentals, flights and activities to your booking. Bundle everything together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Eagle County Regional Airport (EGE) to O'Hare Intl. Airport (ORD)?
You can usually cancel or reschedule your EGE to ORD flight. However, for bookings made more than 24 hours ago, additional fees may apply. Refer to your airline's policies in your itinerary to see what changes are possible and if any costs are involved. You'll also find more details on our Customer Service portal.

Explore a world of travel with Expedia

*Available to One Key members.