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Cheap flights from Vail to Chicago from $231

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Vail to Chicago departing on 12/21. 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
3:05 pm - 10:44 pmEGE-MDW
6h 39m1 stop
Delta Logo
6:00 am - 1:55 pmMDW-EGE
8h 55m1 stop
$414Delta
Find Deal
Thu, Mar 5 - Mon, Mar 9
Delta Logo
3:05 pm - 10:44 pmEGE-MDW
6h 39m1 stop
Delta Logo
9:30 am - 10:54 amMDW-EGE
26h 24m2 stops
$436Delta
Find Deal
Thu, Mar 5 - Mon, Mar 9
Delta Logo
3:05 pm - 10:44 pmEGE-MDW
6h 39m1 stop
Delta Logo
6:00 am - 1:55 pmMDW-EGE
8h 55m1 stop
$444Delta
Find Deal
Thu, Mar 5 - Mon, Mar 9
Delta Logo
3:05 pm - 10:44 pmEGE-MDW
6h 39m1 stop
Delta Logo
9:30 am - 10:54 amMDW-EGE
26h 24m2 stops
$453Delta
Find Deal
Thu, Mar 5 - Mon, Mar 9
Delta Logo
3:05 pm - 10:44 pmEGE-MDW
6h 39m1 stop
Delta Logo
6:00 am - 1:55 pmMDW-EGE
8h 55m1 stop
$519Delta
Find Deal
Thu, Mar 5 - Mon, Mar 9
Delta Logo
11:20 am - 5:19 pmEGE-MDW
4h 59m1 stop
Delta Logo
6:00 am - 2:30 pmMDW-EGE
9h 30m1 stop
$859Delta
Find Deal
Tue, Dec 30 - Wed, Dec 31
Delta Logo
11:20 am - 5:19 pmEGE-MDW
4h 59m1 stop
Delta Logo
6:00 am - 2:30 pmMDW-EGE
9h 30m1 stop
$984Delta
Find Deal
Wed, Dec 24 - Fri, Dec 26
Delta Logo
11:20 am - 10:22 pmEGE-MDW
10h 02m2 stops
Delta Logo
6:00 am - 2:30 pmMDW-EGE
9h 30m1 stop
$1,244Delta
Find Deal
Wed, Dec 24 - Fri, Dec 26
Delta Logo
11:20 am - 10:22 pmEGE-MDW
10h 02m2 stops
Delta Logo
6:00 am - 2:30 pmMDW-EGE
9h 30m1 stop
$1,585Delta
Find Deal
Tue, Dec 30 - Wed, Dec 31

Delta flights from Vail to Chicago Midway Airport

Our best Delta deals on Vail to Chicago Midway Airport flight tickets
Delta
Mar 5
EGE3:05 pmVail Eagle County
6h 39m
1 stop
MDW10:44 pmChicago Midway
Mar 9
MDW6:00 amChicago Midway
8h 55m
1 stop
EGE1:55 pmVail Eagle County
$414
Find similar
Delta
Mar 5
EGE3:05 pmVail Eagle County
6h 39m
1 stop
MDW10:44 pmChicago Midway
Mar 9
MDW9:30 amChicago Midway
26h 24m
2 stops
EGE10:54 amVail Eagle County
$436
Find similar
Delta
Mar 5
EGE3:05 pmVail Eagle County
6h 39m
1 stop
MDW10:44 pmChicago Midway
Mar 9
MDW6:00 amChicago Midway
8h 55m
1 stop
EGE1:55 pmVail Eagle County
$444
Find similar

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 November 4, 2025.
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

Thu 3/5

3:05 pm-10:44 pm

1 stop6h 39m

Chicago Midway

Mon 3/9

6:00 am-1:55 pm

1 stop8h 55m

$414

VailChicago

EGE - MDW

EGEMDW

Vail Eagle County

Thu 3/5

3:05 pm-10:44 pm

1 stop6h 39m

Chicago Midway

Mon 3/9

9:30 am-10:54 am

2 stops26h 24m

$436

VailChicago

EGE - MDW

EGEMDW

Vail Eagle County

Thu 3/5

3:05 pm-10:44 pm

1 stop6h 39m

Chicago Midway

Mon 3/9

6:00 am-1:55 pm

1 stop8h 55m

$444

VailChicago

EGE - MDW

EGEMDW

Vail Eagle County

Thu 3/5

3:05 pm-10:44 pm

1 stop6h 39m

Chicago Midway

Mon 3/9

9:30 am-10:54 am

2 stops26h 24m

$453

VailChicago

EGE - MDW

EGEMDW

Vail Eagle County

Thu 3/5

3:05 pm-10:44 pm

1 stop6h 39m

Chicago Midway

Mon 3/9

6:00 am-1:55 pm

1 stop8h 55m

$519

VailChicago

EGE - MDW

EGEMDW

Vail Eagle County

Tue 12/30

11:20 am-5:19 pm

1 stop4h 59m

Chicago Midway

Wed 12/31

6:00 am-2:30 pm

1 stop9h 30m

$859

VailChicago

EGE - MDW

EGEMDW

Vail Eagle County

Wed 12/24

11:20 am-5:19 pm

1 stop4h 59m

Chicago Midway

Fri 12/26

6:00 am-2:30 pm

1 stop9h 30m

$984

VailChicago

EGE - MDW

EGEMDW

Vail Eagle County

Wed 12/24

11:20 am-10:22 pm

2 stops10h 02m

Chicago Midway

Fri 12/26

6:00 am-2:30 pm

1 stop9h 30m

$1,244

VailChicago

EGE - MDW

EGEMDW

Vail Eagle County

Tue 12/30

11:20 am-10:22 pm

2 stops10h 02m

Chicago Midway

Wed 12/31

6:00 am-2:30 pm

1 stop9h 30m

$1,585

VailChicago

EGE - MDW

EGEMDW

Vail Eagle County

Sun 12/21

11:20 am-5:19 pm

1 stop4h 59m

$231

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 14 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, Friday is the cheapest day to fly to Chicago Midway Airport from Vail. The lowest ticket price found for a Friday departure recently was $224. 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 $290.

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 $173 when looking at flights departing in the evening. Try not to purchase tickets at noon because they tend to be around $313. 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

Direct flights

None
There are no direct flights from Vail to Chicago Midway Airport. There are no popular flight routes from Vail to Chicago Midway Airport.
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  • 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 4h 59m.

  • 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
Merrillville
New Buffalo
Hammond
Benton Harbor
Saint Joseph
Portage
Lansing
Schererville
Valparaiso
Crown Point
Munster
Chesterton
Monticello
Porter
Griffith
Saint John

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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