$231 Cheap Flights from Chicago (MDW) to Vail (EGE)

View $231 flight on Sun, Feb 8, 2026Opens in a new window

Popular airlines from Chicago Midway Airport (MDW) to Vail/Eagle Airport (EGE)

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Cheap Flights from Chicago to Vail (MDW-EGE)

Prices were available within the past 7 days and start at $231 for one-way flights and $309 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Thu, Jan 8 - Thu, Jan 15
MDW
Chicago
EGE
Vail
$309 Roundtrip, found 1 day ago
$309
Roundtrip
found 1 day ago
Select Delta flight, departing Thu, Jan 8 from Chicago to Vail, returning Thu, Jan 15, priced at $309 found 1 day ago
Delta
Thu, Jan 1 - Tue, Jan 13
MDW
Chicago
EGE
Vail
$337 Roundtrip, found 1 day ago
$337
Roundtrip
found 1 day ago
Select Delta flight, departing Thu, Jan 1 from Chicago to Vail, returning Tue, Jan 13, priced at $337 found 1 day ago
Delta
Mon, Jan 12 - Thu, Jan 29
MDW
Chicago
EGE
Vail
$339 Roundtrip, found 1 day ago
$339
Roundtrip
found 1 day ago
Select Delta flight, departing Mon, Jan 12 from Chicago to Vail, returning Thu, Jan 29, priced at $339 found 1 day ago
Delta
Mon, Jan 5 - Fri, Jan 9
MDW
Chicago
EGE
Vail
$351 Roundtrip, found 3 days ago
$351
Roundtrip
found 3 days ago
Select Delta flight, departing Mon, Jan 5 from Chicago to Vail, returning Fri, Jan 9, priced at $351 found 3 days ago
Delta
Wed, Dec 31 - Tue, Jan 13
MDW
Chicago
EGE
Vail
$357 Roundtrip, found 1 day ago
$357
Roundtrip
found 1 day ago
Select Delta flight, departing Wed, Dec 31 from Chicago to Vail, returning Tue, Jan 13, priced at $357 found 1 day ago
Delta
Tue, Jan 13 - Sun, Jan 18
MDW
Chicago
EGE
Vail
$360 Roundtrip, found 2 days ago
$360
Roundtrip
found 2 days ago
Select Delta flight, departing Tue, Jan 13 from Chicago to Vail, returning Sun, Jan 18, priced at $360 found 2 days ago
Delta
Tue, Feb 10 - Thu, Feb 19
MDW
Chicago
EGE
Vail
$369 Roundtrip, found 1 day ago
$369
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Feb 10 from Chicago to Vail, returning Thu, Feb 19, priced at $369 found 1 day ago
Delta
Mon, Jan 5 - Sun, Jan 25
MDW
Chicago
EGE
Vail
$384 Roundtrip, found 1 day ago
$384
Roundtrip
found 1 day ago
Select Delta flight, departing Mon, Jan 5 from Chicago to Vail, returning Sun, Jan 25, priced at $384 found 1 day ago
Delta
Mon, Jan 26 - Thu, Jan 29
MDW
Chicago
EGE
Vail
$385 Roundtrip, found 2 days ago
$385
Roundtrip
found 2 days ago
Select Delta flight, departing Mon, Jan 26 from Chicago to Vail, returning Thu, Jan 29, priced at $385 found 2 days ago
Delta
Thu, Jan 8 - Thu, Jan 15
MDW
Chicago
EGE
Vail
$389 Roundtrip, found 1 day ago
$389
Roundtrip
found 1 day ago
Select Delta flight, departing Thu, Jan 8 from Chicago to Vail, returning Thu, Jan 15, priced at $389 found 1 day ago

Frequently asked questions

How much does a flight from Midway Intl. Airport (MDW) to Eagle County Regional Airport (EGE) cost?
Secure a cheap one-way flight from $231 or cheap return flight from $309 from Midway Intl. Airport (MDW) to Eagle County Regional Airport (EGE) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight deals on this route.
What is the cheapest month to fly from Midway Intl. Airport (MDW) to Eagle County Regional Airport (EGE)?
The cheapest month to fly from MDW to EGE is January, when demand is low. Off-peak season is usually when airlines offer lower prices between these airports.
Which airlines fly direct from Midway Intl. Airport (MDW) to Eagle County Regional Airport (EGE)?
You can't fly nonstop to Eagle County Regional Airport (EGE) from Chicago, IL (MDW-Midway Intl.). However, you can seamlessly travel to Vail without any layovers by leaving from O'Hare Intl. Airport (ORD).
What is the cheapest airline that flies from Midway Intl. Airport (MDW) to Eagle County Regional Airport (EGE)?
Expedia's filter tool lets you easily compare different airlines, flight durations and fares all in one place. Select your preferences, then sort by "Price (lowest to highest)" to find out which carrier offers the cheapest MDW to EGE flight.
How many flights per day from Midway Intl. Airport (MDW) to Eagle County Regional Airport (EGE)?
You'll need to hop on a flight with a layover when traveling from Midway Intl. Airport (MDW) to Eagle County Regional Airport (EGE). There are no daily direct flights on this route. However, just filter your search to include one or more stops to find an option that works for you.
What day of the week has the most flights from MDW to EGE?
Friday is generally the busiest day for flights, while Tuesday is often the quietest.* Just remember that flight schedules can vary based on a range of factors, including the airline and season.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Midway Intl. Airport (MDW) to Eagle County Regional Airport (EGE)?
To reach Eagle County Regional Airport (EGE) on time, opt for a flight that takes off from Midway Intl. Airport (MDW) before 3 PM. The likelihood 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.
Is it cheaper to buy a plane ticket from Midway Intl. Airport (MDW) to Eagle County Regional Airport (EGE) last-minute?
Holding off until just before your departure to book your flight from MDW to EGE often results in higher prices. While you may come across some last-minute discounts, they aren't always guaranteed. Be flexible with your itinerary for the best chance of landing a bargain.
Is it cheaper to book a MDW to EGE flight and hotel package?
Securing a MDW to EGE flight and hotel package tends to be cheaper than booking separately. With Expedia, you can enjoy the convenience of organizing your trip all in one place. Pick from our impressive range of stays and then add flights, car rentals 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 Midway Intl. Airport (MDW) to Eagle County Regional Airport (EGE)?
It's usually possible to cancel or reschedule your MDW to EGE flight. However, if it's been more than 24 hours since booking, additional charges may apply. Refer to your airline's policies in your itinerary to see what changes are possible and whether any costs are involved. You'll also find further details on our Customer Service portal.

Travel information

Origin airport
Midway Intl.
Destination airport
Eagle County Regional
Airlines serving
Delta
Roundtrip price
$308
Distance
1012 mi

Book with confidence

Chicago to Vail Flights

The cheapest times to fly from Chicago to Vail

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 Chicago to Vail are during the month of January. You can find some of the cheapest flights from Chicago to Vail with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Chicago to Vail

Sunday is one of the best days to book for cheap flights from Chicago to Vail: 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 Chicago to Vail

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 Chicago to Vail in 2025. You can also book with separate airlines for your outbound and return journeys, from $231 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 Chicago to Vail 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 Chicago to Vail 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.

 

Chicago to Vail Flights

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*Available to One Key members.