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$141+ 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 1/23. Fares are subject to change and may not be available on all flights or dates of travel.
EGE — MDW
Jan 11 — Jan 181
Sun 1/11
Sun 1/18
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 December 12, 2025.

This Delta deal was found by Cheapflights users on 12/9. 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.
Wed 12/3111:20 amEGE - MDW
1 stop4h 59mDelta
Sat 1/36:00 amMDW - EGE
1 stop9h 30mDelta
Deal found 12/9$674
This Delta deal was found by Cheapflights users on 12/10. 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.
Sun 12/2111:20 amEGE - MDW
1 stop4h 59mDelta
Mon 12/226:00 amMDW - EGE
1 stop9h 30mDelta
Deal found 12/10$810

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 December 12, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$351
(Delta)

One-way from

$141
(Delta)

Popular in

November

Cheapest in

January

Average price

$241
Provider with most accurate pricing for Vail Eagle County-Chicago Midway flight deals.
Search Deals
Provider most trusted by Cheapflights users for Vail Eagle County-Chicago Midway flights.
Search Deals
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. 11% potential increase in price ($28 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 December 2025
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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 December 12, 2025.
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

Wed 1/14

3:10 pm-10:07 pm

1 stop5h 57m

Chicago Midway

Mon 1/19

6:00 am-2:05 pm

1 stop9h 05m

$351

VailChicago

EGE - MDW

EGEMDW

Vail Eagle County

Wed 1/14

3:10 pm-10:07 pm

1 stop5h 57m

Chicago Midway

Tue 1/20

6:00 am-2:05 pm

1 stop9h 05m

$351

VailChicago

EGE - MDW

EGEMDW

Vail Eagle County

Wed 12/31

11:20 am-5:19 pm

1 stop4h 59m

Chicago Midway

Sat 1/3

6:00 am-2:30 pm

1 stop9h 30m

$674

VailChicago

EGE - MDW

EGEMDW

Vail Eagle County

Sun 12/21

11:20 am-5:19 pm

1 stop4h 59m

Chicago Midway

Mon 12/22

6:00 am-2:30 pm

1 stop9h 30m

$810

VailChicago

EGE - MDW

EGEMDW

Vail Eagle County

Fri 1/23

3:10 pm-10:22 pm

1 stop6h 12m

$141

VailChicago

EGE - MDW

EGEMDW

Vail Eagle County

Sat 1/24

3:16 pm-10:22 pm

1 stop6h 06m

$164

VailChicago

EGE - MDW

EGEMDW

Vail Eagle County

Tue 2/10

3:10 pm-10:22 pm

1 stop6h 12m

$290

VailChicago

EGE - MDW

EGEMDW

Vail Eagle County

Sun 12/21

11:20 am-5:19 pm

1 stop4h 59m

$356

VailChicago

EGE - MDW

EGEMDW

Vail Eagle County

Sat 1/24

6:21 pm-10:19 pm

3 stops50h 58m

$449

VailChicago

EGE - MDW

EGEMDW

Vail Eagle County

Fri 1/2

11:20 am-5:19 pm

1 stop4h 59m

$1,241

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/9

Showing 1-10 of 11 results
1
2
  • Most accurate provider: When it comes to deals on Vail-Chicago Midway Airport flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Vail-Chicago Midway Airport flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Vail-Chicago Midway Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Vail-Chicago Midway Airport flights, Cheapflights users trust eDreams the most. eDreams has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Vail-Chicago Midway Airport flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

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, January is the cheapest month in which you can book a flight from Vail to Chicago Midway Airport (average of $57). Flying from Vail to Chicago Midway Airport in October 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 5h 57m. 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, January is the cheapest month in which you can book a flight from Vail to Chicago Midway Airport (average of $57). Flying from Vail to Chicago Midway Airport in October 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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