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Cheap flights from Vail to Chicago from $351

This is the cheapest round-trip flight price found by a momondo user in the last 72 hours by searching for a flight from Vail to Chicago departing on 2/18. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

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Find the cheapest flights from Vail to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
3:10 pm - 10:31 pm
EGE
-
MDW
6h 21m
1 stop
Delta Logo
6:00 am - 2:05 pm
MDW
-
EGE
9h 05m
1 stop
$351Delta
Wed, Feb 18 - Sun, Feb 22
Delta Logo
3:10 pm - 10:31 pm
EGE
-
MDW
6h 21m
1 stop
Delta Logo
6:00 am - 2:05 pm
MDW
-
EGE
9h 05m
1 stop
$446Delta
Mon, Mar 2 - Tue, Mar 3
Delta Logo
3:31 pm - 10:31 pm
EGE
-
MDW
6h 00m
1 stop
Delta Logo
6:00 am - 2:11 pm
MDW
-
EGE
9h 11m
1 stop
$868Delta
Mon, Mar 9 - Sat, Mar 14
Delta Logo
3:10 pm - 10:31 pm
EGE
-
MDW
6h 21m
1 stop
Delta Logo
6:00 am - 2:05 pm
MDW
-
EGE
9h 05m
1 stop
$1,416Delta
Sun, Feb 22 - Mon, Feb 23
Delta Logo
3:10 pm - 10:31 pm
EGE
-
MDW
6h 21m
1 stop
Delta Logo
6:00 am - 2:05 pm
MDW
-
EGE
9h 05m
1 stop
$1,439Delta
Sun, Feb 22 - Wed, Feb 25

Delta flights from Vail to Chicago Midway Airport

Our best Delta deals on Vail to Chicago Midway Airport flight tickets
Delta
Feb 18
EGE3:10 pmVail Eagle County
6h 21m
1 stop
MDW10:31 pmChicago Midway
Feb 22
MDW6:00 amChicago Midway
9h 05m
1 stop
EGE2:05 pmVail Eagle County
$351
Delta
Mar 2
EGE3:10 pmVail Eagle County
6h 21m
1 stop
MDW10:31 pmChicago Midway
Mar 3
MDW6:00 amChicago Midway
9h 05m
1 stop
EGE2:05 pmVail Eagle County
$446
Delta
Mar 9
EGE3:31 pmVail Eagle County
6h 00m
1 stop
MDW10:31 pmChicago Midway
Mar 14
MDW6:00 amChicago Midway
9h 11m
1 stop
EGE2:11 pmVail Eagle County
$868

momondo Fare Finder

 
Customize your flight search to find flights from Vail to Chicago Midway Airport 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, momondo users made 832,500 searches. Data last updated February 3, 2026.
Use the filters below to find and compare flights from Vail to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

VailChicago

EGE - MDW

EGEMDW

Vail Eagle County

Wed 2/18

3:10 pm-10:31 pm

1 stop6h 21m

Chicago Midway

Sun 2/22

6:00 am-2:05 pm

1 stop9h 05m

$351

VailChicago

EGE - MDW

EGEMDW

Vail Eagle County

Mon 3/2

3:10 pm-10:31 pm

1 stop6h 21m

Chicago Midway

Tue 3/3

6:00 am-2:05 pm

1 stop9h 05m

$446

VailChicago

EGE - MDW

EGEMDW

Vail Eagle County

Mon 3/9

3:31 pm-10:31 pm

1 stop6h 00m

Chicago Midway

Sat 3/14

6:00 am-2:11 pm

1 stop9h 11m

$868

VailChicago

EGE - MDW

EGEMDW

Vail Eagle County

Sun 2/22

3:10 pm-10:31 pm

1 stop6h 21m

Chicago Midway

Mon 2/23

6:00 am-2:05 pm

1 stop9h 05m

$1,416

VailChicago

EGE - MDW

EGEMDW

Vail Eagle County

Sun 2/22

3:10 pm-10:31 pm

1 stop6h 21m

Chicago Midway

Wed 2/25

6:00 am-2:05 pm

1 stop9h 05m

$1,439

VailChicago

EGE - MDW

EGEMDW

Vail Eagle County

Sun 2/15

3:10 pm-10:31 pm

1 stop6h 21m

$356

VailChicago

EGE - MDW

EGEMDW

Vail Eagle County

Sat 3/14

11:20 am-6:40 pm

1 stop6h 20m

$630

VailChicago

EGE - MDW

EGEMDW

Vail Eagle County

Sun 3/1

7:00 pm-8:27 pm

3 stops24h 27m

$698

VailChicago

EGE - MDW

EGEMDW

Vail Eagle County

Sat 3/14

11:20 am-6:40 pm

1 stop6h 20m

$765

VailChicago

EGE - MDW

EGEMDW

Vail Eagle County

Sat 3/14

2:39 pm-10:05 am

3 stops42h 26m

$1,137

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 12 resultsSorted by cheapest first
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See travel insights to Chicago from

How to get the cheapest flight ticket from Vail to Chicago Midway Airport

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest day to depart on your flight to Chicago Midway Airport?

According to our data, Monday is the cheapest day to fly to Chicago Midway Airport from Vail. The lowest ticket price found for a Monday departure recently was $225. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Sunday is the most expensive day to depart from Vail because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $294.

What is the cheapest time of day to depart on your flight to Chicago Midway Airport?

Flying to Chicago Midway Airport from Vail in the evening is the least expensive time of day to depart. momondo users have found prices as low as $190 when looking at flights departing in the evening. Try not to purchase tickets at noon because they tend to be around $327. Of course, these prices can vary depending on the time of year and what airport you fly to.

When to book flights from Vail to Chicago Midway Airport

Are you open to changing your travel dates? Check out the ideal times to fly from Vail to Chicago Midway Airport according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Vail to Chicago Midway Airport (EGE to MDW) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Vail to Chicago Midway Airport

Fastest flight time

6h 00m

Direct flights

None
The fastest flight from Vail to Chicago Midway Airport takes 6h 00m
There are no direct flights from Vail to Chicago Midway Airport. There are no popular flight routes from Vail to Chicago Midway Airport.
Search flight deals

  • How far is Vail Eagle County to Chicago Midway by plane?

    Vail Eagle County and Chicago Midway are 984.1 mi apart from one another. A reasonable flight in good conditions will take 6h 00m.

  • When did momondo last update prices for flights from Vail Eagle County Airport to Chicago Midway Airport?

    Prices for flights from Vail Eagle County Airport to Chicago Midway Airport were last updated today.

  • How old do you have to be to fly from Vail Eagle County Airport to Chicago Midway Airport?

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Vail Eagle County Airport to Chicago Midway Airport.

  • What documentation or ID do you need to fly to Chicago Midway Airport?

    The travel and health documents required for your trip to Chicago Midway Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago Midway Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
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Why use momondo?

Why should I use momondo to find a flight deal from Vail to Chicago?

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Vail to Chicago for you.

Can I find flights from Vail to Chicago with flexible booking policies on momondo?

Yes. momondo allows you to filter the results for Vail to Chicago flights to just show those with flexible booking policies.

How can momondo help me find flights from Vail to Chicago?

Once all potential Vail to Chicago flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

I’m not ready to book a flight from Vail to Chicago right now. Can momondo alert me if prices change?

If you are not ready to book a flight from Vail to Chicago now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Chicago and let you know when they change.

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