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$266+ Cheap flights from Vail (EGE) to Midway (MDW)

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 2/6. Fares are subject to change and may not be available on all flights or dates of travel.
EGE — MDW
Feb 25 — Mar 41
Wed 2/25
Wed 3/4
1 adult, Economy
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Cheap flight deals from Vail to Midway

Cheapest flights from Vail to Midway
Explore the most affordable flight options available from Vail to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 26, 2026.

This Delta deal was found by Cheapflights users on 1/24. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 1/273:10 pm
EGE
-
MDW
1 stop6h 12m
Delta
Fri 1/306:00 am
MDW
-
EGE
1 stop9h 05m
Delta
Deal found 1/24$591
This Delta deal was found by Cheapflights users on 1/25. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/53:10 pm
EGE
-
MDW
1 stop6h 12m
Delta
Sun 2/86:00 am
MDW
-
EGE
1 stop9h 05m
Delta
Deal found 1/25$620
This Delta deal was found by Cheapflights users on 1/25. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/73:16 pm
EGE
-
MDW
1 stop6h 06m
Delta
Wed 2/116:00 am
MDW
-
EGE
1 stop9h 05m
Delta
Deal found 1/25$819
This Delta deal was found by Cheapflights users on 1/25. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/263:10 pm
EGE
-
MDW
1 stop6h 21m
Delta
Sat 2/286:00 am
MDW
-
EGE
1 stop9h 05m
Delta
Deal found 1/25$1,416

Find flight deals from Vail to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Vail (EGE) to Midway (MDW). 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 January 26, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$620
(Delta)

One-way from

$266
(Delta)

Popular in

November

Cheapest in

February

Average price

$212
Provider with most accurate pricing for Denver Intl-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Denver Intl-Chicago (CHI) flights.
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From Vail Eagle County to Chicago Midway
Search Deals
One-way flight from Vail Eagle County to Chicago Midway
Search Deals
Highest demand for flights based on searches. 8% potential increase in price ($20 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
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Average for round-trip flights in January 2026
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Cheapflights Fare Finder

 
Customize your flight search to find flights from Vail to Midway 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 January 26, 2026.
Use the filters below to find and compare flights from Vail to Chicago Midway Airport that are best for you.

Fly from

Vail

Fly to

Midway

Route

Depart

Return

Price

VailChicago

EGE - MDW

EGEMDW

Vail Eagle County

Thu 2/5

3:10 pm-10:22 pm

1 stop6h 12m

Chicago Midway

Sun 2/8

6:00 am-2:05 pm

1 stop9h 05m

$620

VailChicago

EGE - MDW

EGEMDW

Vail Eagle County

Sat 2/7

3:16 pm-10:22 pm

1 stop6h 06m

Chicago Midway

Wed 2/11

6:00 am-2:05 pm

1 stop9h 05m

$819

VailChicago

EGE - MDW

EGEMDW

Vail Eagle County

Thu 2/26

3:10 pm-10:31 pm

1 stop6h 21m

Chicago Midway

Sat 2/28

6:00 am-2:05 pm

1 stop9h 05m

$1,416

VailChicago

EGE - MDW

EGEMDW

Vail Eagle County

Fri 2/6

3:10 pm-10:22 pm

1 stop6h 12m

$266

VailChicago

EGE - MDW

EGEMDW

Vail Eagle County

Sat 2/28

4:23 pm-10:05 am

2 stops40h 42m

$426

VailChicago

EGE - MDW

EGEMDW

Vail Eagle County

Sun 2/8

3:10 pm-10:22 pm

1 stop6h 12m

$640

VailChicago

EGE - MDW

EGEMDW

Vail Eagle County

Sat 2/28

3:10 pm-10:31 pm

1 stop6h 21m

$640

VailChicago

EGE - MDW

EGEMDW

Vail Eagle County

Fri 2/6

1:36 pm-11:45 am

3 stops45h 09m

$654

VailChicago

EGE - MDW

EGEMDW

Vail Eagle County

Wed 3/25

3:31 pm-10:31 pm

1 stop6h 00m

$1,537

VailChicago

EGE - MDW

EGEMDW

Vail Eagle County

Tue 2/17

3:10 pm-10:33 pm

1 stop6h 23m

$1,837

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/23

Best time to book a flight from Vail to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway 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 Midway Airport

What is the cheapest month to book a flight from Vail to Chicago Midway Airport?

Currently, February is the cheapest month in which you can book a flight from Vail to Chicago Midway Airport (average of $60). Flying from Vail to Chicago Midway Airport in July is currently the most expensive (average of $156). 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.

Related info for your journey

Find useful and relevant information for your journey from Vail to Midway. 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 Midway?

    For a flight from Vail to Chicago Midway, you will be flying from Eagle County. Vail Eagle County (EGE) is just 28.9 mi from the center of the city. Eagle County is the only Vail airport and it handles 0 outbound flights to Chicago Midway per day. 0 airlines have flights to Chicago Midway from Vail Eagle County on a regular basis.

  • How long is the flight from Vail to Chicago Midway Airport?

    There are many flights that can get you from Vail to Chicago Midway Airport in 6h 12m. Fly via Delta to get the fastest option. There are 1012 mi between Vail and Chicago Midway Airport.

  • Can I find deals for flights from Vail to Midway that include hotel bookings?

    Yes. In addition to deals on Vail to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Vail to Midway?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Vail to Midway.

  • Can I find deals for business class flights from Vail to Midway?

    Yes. Cheapflights offers flight deals from Vail to Midway 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 Midway Airport?

    Currently, February is the cheapest month in which you can book a flight from Vail to Chicago Midway Airport (average of $60). Flying from Vail to Chicago Midway Airport in July is currently the most expensive (average of $156). 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 Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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