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Cheap flights from Aspen to Chicago from $253

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Aspen to Chicago departing on 8/22. 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

Find the cheapest flights from Aspen to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
8:05 am - 4:27 pm
ASE
-
MDW
7h 22m
1 stop
Delta Logo
6:00 am - 11:21 am
MDW
-
ASE
6h 21m
1 stop
$444Delta
Wed, Aug 26 - Sat, Aug 29
Delta Logo
8:05 am - 4:27 pm
ASE
-
MDW
7h 22m
1 stop
Delta Logo
6:00 am - 11:21 am
MDW
-
ASE
6h 21m
1 stop
$469Delta
Wed, Aug 26 - Sat, Aug 29
Delta Logo
8:05 am - 4:27 pm
ASE
-
MDW
7h 22m
1 stop
Delta Logo
6:00 am - 11:21 am
MDW
-
ASE
6h 21m
1 stop
$504Delta
Wed, Aug 26 - Sat, Aug 29
Delta Logo
8:05 am - 6:31 pm
ASE
-
MDW
9h 26m
2 stops
Delta Logo
6:00 am - 11:21 am
MDW
-
ASE
6h 21m
1 stop
$611Delta
Fri, Sep 25 - Sun, Oct 4
Delta Logo
8:05 am - 4:12 pm
ASE
-
MDW
7h 07m
1 stop
Delta Logo
6:00 am - 11:23 am
MDW
-
ASE
6h 23m
1 stop
$634Delta
Sun, May 31 - Sun, Jun 7
Delta Logo
8:05 am - 6:31 pm
ASE
-
MDW
9h 26m
2 stops
Delta Logo
6:00 am - 11:21 am
MDW
-
ASE
6h 21m
1 stop
$654Delta
Wed, Aug 26 - Sat, Aug 29
Delta Logo
8:05 am - 6:31 pm
ASE
-
MDW
9h 26m
2 stops
Delta Logo
6:00 am - 11:21 am
MDW
-
ASE
6h 21m
1 stop
$664Delta
Wed, Aug 26 - Sat, Aug 29
Delta Logo
8:05 am - 4:27 pm
ASE
-
MDW
7h 22m
1 stop
Delta Logo
6:00 am - 11:21 am
MDW
-
ASE
6h 21m
1 stop
$686Delta
Fri, Sep 25 - Sun, Oct 4
Delta Logo
8:05 am - 6:31 pm
ASE
-
MDW
9h 26m
2 stops
Delta Logo
6:00 am - 11:21 am
MDW
-
ASE
6h 21m
1 stop
$744Delta
Wed, Aug 26 - Sat, Aug 29
Delta Logo
7:36 am - 4:16 pm
ASE
-
MDW
7h 40m
1 stop
Delta Logo
6:00 am - 11:23 am
MDW
-
ASE
6h 23m
1 stop
$829Delta
Tue, Jun 16 - Fri, Jun 19

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Delta flights from Aspen to Chicago Midway Airport

Our best Delta deals on Aspen to Chicago Midway Airport flight tickets
Delta
Aug 26
ASE8:05 amAspen Pitkin County
7h 22m
1 stop
MDW4:27 pmChicago Midway
Aug 29
MDW6:00 amChicago Midway
6h 21m
1 stop
ASE11:21 amAspen Pitkin County
$444
Delta
Aug 26
ASE8:05 amAspen Pitkin County
7h 22m
1 stop
MDW4:27 pmChicago Midway
Aug 29
MDW6:00 amChicago Midway
6h 21m
1 stop
ASE11:21 amAspen Pitkin County
$469
Delta
Aug 26
ASE8:05 amAspen Pitkin County
7h 22m
1 stop
MDW4:27 pmChicago Midway
Aug 29
MDW6:00 amChicago Midway
6h 21m
1 stop
ASE11:21 amAspen Pitkin County
$504

momondo Fare Finder

 
Customize your flight search to find flights from Aspen 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 May 2, 2026.
Use the filters below to find and compare flights from Aspen to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

AspenChicago

ASE - MDW

ASEMDW

Aspen Pitkin County

Wed 8/26

8:05 am-4:27 pm

1 stop7h 22m

Chicago Midway

Sat 8/29

6:00 am-11:21 am

1 stop6h 21m

$444

AspenChicago

ASE - MDW

ASEMDW

Aspen Pitkin County

Wed 8/26

8:05 am-4:27 pm

1 stop7h 22m

Chicago Midway

Sat 8/29

6:00 am-11:21 am

1 stop6h 21m

$469

AspenChicago

ASE - MDW

ASEMDW

Aspen Pitkin County

Wed 8/26

8:05 am-4:27 pm

1 stop7h 22m

Chicago Midway

Sat 8/29

6:00 am-11:21 am

1 stop6h 21m

$504

AspenChicago

ASE - MDW

ASEMDW

Aspen Pitkin County

Fri 9/25

8:05 am-6:31 pm

2 stops9h 26m

Chicago Midway

Sun 10/4

6:00 am-11:21 am

1 stop6h 21m

$611
Quickest round-trip

AspenChicago

ASE - MDW

ASEMDW

Aspen Pitkin County

Sun 5/31

8:05 am-4:12 pm

1 stop7h 07m

Chicago Midway

Sun 6/7

6:00 am-11:23 am

1 stop6h 23m

$634

AspenChicago

ASE - MDW

ASEMDW

Aspen Pitkin County

Wed 8/26

8:05 am-6:31 pm

2 stops9h 26m

Chicago Midway

Sat 8/29

6:00 am-11:21 am

1 stop6h 21m

$654

AspenChicago

ASE - MDW

ASEMDW

Aspen Pitkin County

Wed 8/26

8:05 am-6:31 pm

2 stops9h 26m

Chicago Midway

Sat 8/29

6:00 am-11:21 am

1 stop6h 21m

$664

AspenChicago

ASE - MDW

ASEMDW

Aspen Pitkin County

Fri 9/25

8:05 am-4:27 pm

1 stop7h 22m

Chicago Midway

Sun 10/4

6:00 am-11:21 am

1 stop6h 21m

$686

AspenChicago

ASE - MDW

ASEMDW

Aspen Pitkin County

Wed 8/26

8:05 am-6:31 pm

2 stops9h 26m

Chicago Midway

Sat 8/29

6:00 am-11:21 am

1 stop6h 21m

$744

AspenChicago

ASE - MDW

ASEMDW

Aspen Pitkin County

Tue 6/16

7:36 am-4:16 pm

1 stop7h 40m

Chicago Midway

Fri 6/19

6:00 am-11:23 am

1 stop6h 23m

$829

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 16 resultsSorted by cheapest first
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See travel insights to Chicago from

How to get the cheapest flight ticket from Aspen 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 airline that flies from Aspen Pitkin County to Chicago Midway?

Delta is the most popular carrier operating from Aspen Pitkin County to Chicago Midway

When to book flights from Aspen to Chicago Midway Airport

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

Cheap Aspen to Chicago Midway Airport (ASE to MDW) flight deals and tips

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

Fastest flight time

7h 07m

Direct flights

None
The fastest flight from Aspen to Chicago Midway Airport takes 7h 07m
There are no direct flights from Aspen to Chicago Midway Airport. There are no popular flight routes from Aspen to Chicago Midway Airport.
Search flight deals

Frequently asked questions about flying from Aspen to Chicago Midway Airport

  • How far is Aspen Pitkin County to Chicago Midway by plane?

    Aspen Pitkin County and Chicago Midway are 1015.2 mi apart from one another. In terms of flight time, this usually takes a little over 7h 07m.

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

    Prices for flights from Aspen Pitkin County Airport to Chicago Midway Airport refresh daily.

  • How old do you have to be to fly from Aspen Pitkin 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 Aspen Pitkin 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
Saint Joseph
Benton Harbor
Portage
Lansing
Valparaiso
Munster
Schererville
Crown Point
Monticello
Chesterton
Porter
Griffith
Saint John

Why use momondo?

Why should I use momondo to find a flight deal from Aspen 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 Aspen to Chicago for you.

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

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

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

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Chicago from Aspen.

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

Yes momondo offers price alerts on flights to Chicago from Aspen. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.

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