$137 Cheap Flights from Vail (EGE) to Chicago (MDW)

View $137 flight on Fri, Jan 9, 2026Opens in a new window

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

Cheap Flights from Vail to Chicago (EGE-MDW)

Prices were available within the past 7 days and start at $137 for one-way flights and $419 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Fri, Feb 6 - Sun, Feb 8
EGE
Vail
MDW
Chicago
$419 Roundtrip, found 2 days ago
$419
Roundtrip
found 2 days ago
Select Delta flight, departing Fri, Feb 6 from Vail to Chicago, returning Sun, Feb 8, priced at $419 found 2 days ago
Delta
Wed, Feb 25 - Mon, Mar 2
EGE
Vail
MDW
Chicago
$448 Roundtrip, found 2 days ago
$448
Roundtrip
found 2 days ago
Select Delta flight, departing Wed, Feb 25 from Vail to Chicago, returning Mon, Mar 2, priced at $448 found 2 days ago
Delta
Mon, Dec 22 - Mon, Jan 12
EGE
Vail
MDW
Chicago
$476 Roundtrip, found 5 days ago
$476
Roundtrip
found 5 days ago
Select Delta flight, departing Mon, Dec 22 from Vail to Chicago, returning Mon, Jan 12, priced at $476 found 5 days ago
Delta
Tue, Dec 30 - Mon, Jan 5
EGE
Vail
MDW
Chicago
$494 Roundtrip, found 16 hours ago
$494
Roundtrip
found 16 hours ago
Select Delta flight, departing Tue, Dec 30 from Vail to Chicago, returning Mon, Jan 5, priced at $494 found 16 hours ago
Delta
Wed, Feb 25 - Mon, Mar 2
EGE
Vail
MDW
Chicago
$509 Roundtrip, found 2 days ago
$509
Roundtrip
found 2 days ago
Select Delta flight, departing Wed, Feb 25 from Vail to Chicago, returning Mon, Mar 2, priced at $509 found 2 days ago
Delta
Tue, Dec 30 - Mon, Jan 5
EGE
Vail
MDW
Chicago
$514 Roundtrip, found 1 day ago
$514
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Dec 30 from Vail to Chicago, returning Mon, Jan 5, priced at $514 found 1 day ago
Delta
Fri, Feb 6 - Sun, Feb 8
EGE
Vail
MDW
Chicago
$519 Roundtrip, found 2 days ago
$519
Roundtrip
found 2 days ago
Select Delta flight, departing Fri, Feb 6 from Vail to Chicago, returning Sun, Feb 8, priced at $519 found 2 days ago
Delta
Sun, Jan 18 - Fri, Jan 23
EGE
Vail
MDW
Chicago
$530 Roundtrip, found 3 hours ago
$530
Roundtrip
found 3 hours ago
Select Delta flight, departing Sun, Jan 18 from Vail to Chicago, returning Fri, Jan 23, priced at $530 found 3 hours ago
Delta
Wed, Feb 25 - Mon, Mar 2
EGE
Vail
MDW
Chicago
$576 Roundtrip, found 2 days ago
$576
Roundtrip
found 2 days ago
Select Delta flight, departing Wed, Feb 25 from Vail to Chicago, returning Mon, Mar 2, priced at $576 found 2 days ago
United
Tue, Nov 25 - Mon, Dec 1
EGE
Vail
MDW
Chicago
$1,733 Roundtrip, found 4 days ago
$1,733
Roundtrip
found 4 days ago
Select United flight, departing Tue, Nov 25 from Vail to Chicago, returning Mon, Dec 1, priced at $1,733 found 4 days ago

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 $399
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from $399

Frequently asked questions

How much does a flight from Eagle County Regional Airport (EGE) to Midway Intl. Airport (MDW) cost?
Snag a cheap one-way flight from $137 or cheap return flight from $419 from Eagle County Regional Airport (EGE) to Midway Intl. Airport (MDW) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to see our cheapest flight deals on this route.
What is the cheapest month to fly from Eagle County Regional Airport (EGE) to Midway Intl. Airport (MDW)?
February is the least expensive month to fly from EGE to MDW. Planning your trip for the off-season is often the key to better flight prices.
What is the cheapest airline that flies from Eagle County Regional Airport (EGE) to Midway Intl. Airport (MDW)?
To find the cheapest airline that'll fly you from EGE to MDW, use Expedia's filter tool. Customize your search based on your travel style, such as preferred carriers and flight duration. You can then sort your results by "Price (lowest to highest)" to see the most affordable options first.
How many flights per day from Eagle County Regional Airport (EGE) to Midway Intl. Airport (MDW)?
There are no daily direct flights departing from Eagle County Regional Airport (EGE) to Midway Intl. Airport (MDW). But you can book flights with layovers. Filter your search on Expedia to include one or two stops, and you'll be on your way before you know it.
What day of the week has the most flights from EGE to MDW?
You'll generally find Tuesday the quietest day for flights, while Fridays are often the busiest.* However this can change from season to season and during peak travel times or public holidays.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Eagle County Regional Airport (EGE) to Midway Intl. Airport (MDW)?
To arrive at Midway Intl. Airport (MDW) on schedule, select 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 hour.**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)?
If you're on a direct flight from Eagle County Regional Airport (EGE) to Chicago, O'Hare Intl. Airport (ORD) is the only airport you can land at.
Is it cheaper to buy a plane ticket from Eagle County Regional Airport (EGE) to Midway Intl. Airport (MDW) last-minute?
Booking your ticket from EGE to MDW just before your trip is usually more expensive. However, if you're flexible with your travel dates and times, you could grab a cheap last-minute fare.
Is it cheaper to book an EGE to MDW flight and hotel package?
Compared with arranging hotels and flights separately, booking an EGE to MDW flight and hotel package with Expedia could result in significant savings. Better still, having everything in one place takes the hassle out of travel planning. Simply pick your flights and select from our extensive range of stays, then customize your trip with other add-ons like car rentals and activities.
Can I cancel or change the date of my flight from Eagle County Regional Airport (EGE) to Midway Intl. Airport (MDW)?
In most cases, you're able to cancel or reschedule your EGE to MDW flight. However, there may be additional fees, especially if your booking was made more than 24 hours ago. Double-check your itinerary for the airline's policies and fees on flight changes, or if you want more details, head to our Customer Service portal.

Travel information

Travel information

Origin airport
Eagle County Regional
Destination airport
Midway Intl.
Airlines serving
Delta
Roundtrip price
$418
Distance
1012 mi

Book with confidence

Book with confidence

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 $137 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.

 

Vail to Chicago Flights

Explore a world of travel with Expedia

Explore a world of travel with Expedia

*Available to One Key members.