Latest deals
Insights
When to book
FAQs
Price Alerts

Cheap flights from Aspen to Chicago from $210

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 10/23. 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

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

Find the cheapest flights from Aspen to Chicago

Cheap round-trip flights

Delta Logo
7:16 am - 6:37 pmASE-MDW
10h 21m2 stops
Delta Logo
6:00 am - 11:21 amMDW-ASE
6h 21m1 stop
$483Delta
Find Deal
Fri, Sep 5 - Sun, Sep 7
Delta Logo
7:21 am - 4:09 pmASE-MDW
7h 48m1 stop
Delta Logo
6:00 am - 11:29 amMDW-ASE
6h 29m1 stop
$689Delta
Find Deal
Thu, Oct 16 - Mon, Oct 20
Delta Logo
7:21 am - 6:25 pmASE-MDW
10h 04m2 stops
Delta Logo
6:00 am - 11:29 amMDW-ASE
6h 29m1 stop
$814Delta
Find Deal
Thu, Oct 16 - Mon, Oct 20

Delta flights from Aspen to Chicago Midway Airport

Our best Delta deals on Aspen to Chicago Midway Airport flight tickets
Delta
Sep 5
ASE7:16 amAspen Pitkin County
10h 21m
2 stops
MDW6:37 pmChicago Midway
Sep 7
MDW6:00 amChicago Midway
6h 21m
1 stop
ASE11:21 amAspen Pitkin County
$483
Find similar
Delta
Oct 16
ASE7:21 amAspen Pitkin County
7h 48m
1 stop
MDW4:09 pmChicago Midway
Oct 20
MDW6:00 amChicago Midway
6h 29m
1 stop
ASE11:29 amAspen Pitkin County
$689
Find similar
Delta
Oct 16
ASE7:21 amAspen Pitkin County
10h 04m
2 stops
MDW6:25 pmChicago Midway
Oct 20
MDW6:00 amChicago Midway
6h 29m
1 stop
ASE11:29 amAspen Pitkin County
$814
Find similar

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 July 31, 2025.
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

AspenChicago

ASE - MDW

ASEMDW

Aspen Pitkin County

Fri 9/5

7:16 am-6:37 pm

2 stops10h 21m

Chicago Midway

Sun 9/7

6:00 am-11:21 am

1 stop6h 21m

$483

AspenChicago

ASE - MDW

ASEMDW

Aspen Pitkin County

Thu 10/16

7:21 am-4:09 pm

1 stop7h 48m

Chicago Midway

Mon 10/20

6:00 am-11:29 am

1 stop6h 29m

$689

AspenChicago

ASE - MDW

ASEMDW

Aspen Pitkin County

Thu 10/16

7:21 am-6:25 pm

2 stops10h 04m

Chicago Midway

Mon 10/20

6:00 am-11:29 am

1 stop6h 29m

$814

AspenChicago

ASE - MDW

ASEMDW

Aspen Pitkin County

Thu 10/23

7:21 am-4:09 pm

1 stop7h 48m

$210

AspenChicago

ASE - MDW

ASEMDW

Aspen Pitkin County

Thu 10/23

7:21 am-4:09 pm

1 stop7h 48m

$260

AspenChicago

ASE - MDW

ASEMDW

Aspen Pitkin County

Sat 9/27

7:16 am-6:35 pm

2 stops10h 19m

$275

AspenChicago

ASE - MDW

ASEMDW

Aspen Pitkin County

Sat 9/27

7:16 am-3:26 pm

1 stop7h 10m

$330

AspenChicago

ASE - MDW

ASEMDW

Aspen Pitkin County

Thu 10/23

7:21 am-6:25 pm

2 stops10h 04m

$485

AspenChicago

ASE - MDW

ASEMDW

Aspen Pitkin County

Wed 8/6

8:05 am-4:20 pm

1 stop7h 15m

$1,201

AspenChicago

ASE - MDW

ASEMDW

Aspen Pitkin County

Fri 8/15

7:16 am-5:37 pm

2 stops9h 21m

$1,206

Flights are sorted by cheapest round-trip flights first.

Sorted by cheapest first

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

Best Price Found

$210

Fastest flight time

7h 10m

Direct flights

None
The best one-way flight to Chicago Midway Airport from Aspen in the past 72 hours is $210. The best round-trip flight deal from Aspen to Chicago Midway Airport found on momondo in the last 72 hours is $483.
The fastest flight from Aspen to Chicago Midway Airport takes 7h 10m
There are no direct flights from Aspen to Chicago Midway Airport. Popular non-direct route for this connection is Aspen Pitkin County Airport - Chicago Midway Airport.
Search flight deals

  • 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 48m.

  • 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
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 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.

An easier way to manage your Chicago Midway Airport trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Tue 8/5
Tue 8/12
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Chicago