$182 Cheap Flights from Vail (EGE) to Chicago (ORD)

View $182 flight on Mon, Nov 17, 2025Opens in a new window

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

Cheap Flights from Vail to Chicago (EGE-ORD)

Prices were available within the past 7 days and start at $182 for one-way flights and $289 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

United
Fri, Jan 16 - Tue, Jan 20
EGE
Vail
ORD
Chicago
$289 Roundtrip, found 10 hours ago
$289
Roundtrip
found 10 hours ago
Select United flight, departing Fri, Jan 16 from Vail to Chicago, returning Tue, Jan 20, priced at $289 found 10 hours ago
American Airlines
Tue, Dec 30 - Sat, Jan 3
EGE
Vail
ORD
Chicago
$299 Roundtrip, found 7 hours ago
$299
Roundtrip
found 7 hours ago
Select American Airlines flight, departing Tue, Dec 30 from Vail to Chicago, returning Sat, Jan 3, priced at $299 found 7 hours ago
Delta
Fri, Jan 16 - Tue, Jan 20
EGE
Vail
ORD
Chicago
$309 Roundtrip, found 10 hours ago
$309
Roundtrip
found 10 hours ago
Select Delta flight, departing Fri, Jan 16 from Vail to Chicago, returning Tue, Jan 20, priced at $309 found 10 hours ago
American Airlines
Tue, Dec 30 - Sat, Jan 3
EGE
Vail
ORD
Chicago
$310 Roundtrip, found 7 hours ago
$310
Roundtrip
found 7 hours ago
Select American Airlines flight, departing Tue, Dec 30 from Vail to Chicago, returning Sat, Jan 3, priced at $310 found 7 hours ago
United
Thu, Feb 26 - Sun, Mar 1
EGE
Vail
ORD
Chicago
$315 Roundtrip, found 2 days ago
$315
Roundtrip
found 2 days ago
Select United flight, departing Thu, Feb 26 from Vail to Chicago, returning Sun, Mar 1, priced at $315 found 2 days ago
United
Sat, Dec 27 - Wed, Dec 31
EGE
Vail
ORD
Chicago
$316 Roundtrip, found 4 days ago
$316
Roundtrip
found 4 days ago
Select United flight, departing Sat, Dec 27 from Vail to Chicago, returning Wed, Dec 31, priced at $316 found 4 days ago
United
Sat, Dec 27 - Wed, Dec 31
EGE
Vail
ORD
Chicago
$319 Roundtrip, found 4 days ago
$319
Roundtrip
found 4 days ago
Select United flight, departing Sat, Dec 27 from Vail to Chicago, returning Wed, Dec 31, priced at $319 found 4 days ago
United
Thu, Feb 26 - Sun, Mar 1
EGE
Vail
ORD
Chicago
$319 Roundtrip, found 2 days ago
$319
Roundtrip
found 2 days ago
Select United flight, departing Thu, Feb 26 from Vail to Chicago, returning Sun, Mar 1, priced at $319 found 2 days ago
American Airlines
Tue, Dec 30 - Sat, Jan 3
EGE
Vail
ORD
Chicago
$320 Roundtrip, found 7 hours ago
$320
Roundtrip
found 7 hours ago
Select American Airlines flight, departing Tue, Dec 30 from Vail to Chicago, returning Sat, Jan 3, priced at $320 found 7 hours ago
Alaska Airlines
Wed, Feb 4 - Sun, Feb 8
EGE
Vail
ORD
Chicago
$613 Roundtrip, found 2 days ago
$613
Roundtrip
found 2 days ago
Select Alaska Airlines flight, departing Wed, Feb 4 from Vail to Chicago, returning Sun, Feb 8, priced at $613 found 2 days 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.

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 $391
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from $391
Flights from Vail (EGE) to Chicago (ORD)
Origin airport
Eagle County Regional
Destination airport
O'Hare Intl.
Airlines serving
Alaska Airlines, American Airlines, Delta, United
Roundtrip price
$289
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 January. 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 $182 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?
Snag a cheap one-way flight from $182 or cheap return flight from $289 from Eagle County Regional Airport (EGE) to O'Hare Intl. Airport (ORD) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight offers on this route.
What is the cheapest month to fly from Eagle County Regional Airport (EGE) to O'Hare Intl. Airport (ORD)?
The cheapest month to fly from EGE to ORD is January, when there's less demand. Off-peak season is typically when you'll find cheap fares for travel between these airports.
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 Eagle County Regional Airport (EGE) to O'Hare Intl. Airport (ORD)?
American Airlines and United Airlines are some well-known airlines offering competitive fares. Remember that flight prices from Eagle County Regional Airport (EGE) to O'Hare Intl. Airport (ORD) can change based on travel dates, demand and how early you book. With Expedia's search tool, you can easily find an EGE to ORD flight that suits your plans and budget.
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.

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*Available to One Key members.