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$221+ Cheap flights from Midway (MDW) to Aspen (ASE)

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 3/11. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — ASE
Feb 20 — Feb 271
Fri 2/20
Fri 2/27
1 adult, Economy
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Cheap flight deals from Midway to Aspen

Cheapest flights from Midway to Aspen
Explore the most affordable flight options available from Midway to Aspen. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 21, 2026.

This Delta deal was found by Cheapflights users on 1/20. 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 1/256:00 am
MDW
-
ASE
1 stop9h 16m
Delta
Tue 1/273:04 pm
ASE
-
MDW
1 stop6h 18m
Delta
Deal found 1/20$526
This Delta deal was found by Cheapflights users on 1/19. 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 1/216:00 am
MDW
-
ASE
1 stop9h 16m
Delta
Thu 1/223:04 pm
ASE
-
MDW
1 stop6h 18m
Delta
Deal found 1/19$551
This Delta deal was found by Cheapflights users on 1/20. 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 1/286:00 am
MDW
-
ASE
1 stop6h 43m
Delta
Sat 1/313:04 pm
ASE
-
MDW
1 stop6h 18m
Delta
Deal found 1/20$591
This Delta deal was found by Cheapflights users on 1/19. 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 8/266:00 am
MDW
-
ASE
1 stop6h 21m
Delta
Sun 8/308:05 am
ASE
-
MDW
1 stop7h 22m
Delta
Deal found 1/19$625
This Delta deal was found by Cheapflights users on 1/19. 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 2/226:00 am
MDW
-
ASE
1 stop9h 14m
Delta
Fri 2/273:00 pm
ASE
-
MDW
1 stop6h 31m
Delta
Deal found 1/19$711
This Delta deal was found by Cheapflights users on 1/19. 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.
Mon 6/226:00 am
MDW
-
ASE
1 stop6h 29m
Delta
Wed 7/18:05 am
ASE
-
MDW
1 stop7h 20m
Delta
Deal found 1/19$830

Find flight deals from Midway to Aspen

Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to Aspen (ASE). 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 January 21, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

Expedia
3 stars

Round-trip from

$711
(Delta)

One-way from

$221
(Delta)

Popular in

April

Cheapest in

September

Average price

$641
Provider with most accurate pricing for Chicago Midway-Aspen Pitkin County flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago Midway-Aspen Pitkin County flights.
Search Deals
From Chicago Midway to Aspen Pitkin County
Search Deals
One-way flight from Chicago Midway to Aspen Pitkin County
Search Deals
Highest demand for flights based on searches. 6% potential increase in price ($38 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($12 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Midway to Aspen 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 January 21, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Aspen that are best for you.

Fly from

Midway

Fly to

Aspen

Route

Depart

Return

Price

ChicagoAspen

MDW - ASE

MDWASE

Chicago Midway

Sun 1/25

6:00 am-2:16 pm

1 stop9h 16m

Aspen Pitkin County

Tue 1/27

3:04 pm-10:22 pm

1 stop6h 18m

$526

ChicagoAspen

MDW - ASE

MDWASE

Chicago Midway

Wed 1/28

6:00 am-11:43 am

1 stop6h 43m

Aspen Pitkin County

Sat 1/31

3:04 pm-10:22 pm

1 stop6h 18m

$591

ChicagoAspen

MDW - ASE

MDWASE

Chicago Midway

Sun 2/22

6:00 am-2:14 pm

1 stop9h 14m

Aspen Pitkin County

Fri 2/27

3:00 pm-10:31 pm

1 stop6h 31m

$711

ChicagoAspen

MDW - ASE

MDWASE

Chicago Midway

Sat 4/11

6:00 am-11:40 am

1 stop6h 40m

Aspen Pitkin County

Mon 4/13

1:33 pm-10:29 pm

1 stop7h 56m

$914

ChicagoAspen

MDW - ASE

MDWASE

Chicago Midway

Sun 3/1

6:00 am-2:14 pm

1 stop9h 14m

Aspen Pitkin County

Tue 3/3

3:00 pm-10:33 pm

1 stop6h 33m

$915

ChicagoAspen

MDW - ASE

MDWASE

Chicago Midway

Fri 1/30

6:00 am-11:43 am

1 stop6h 43m

Aspen Pitkin County

Mon 3/2

3:00 pm-10:31 pm

1 stop6h 31m

$989

ChicagoAspen

MDW - ASE

MDWASE

Chicago Midway

Sat 4/4

6:00 am-11:40 am

1 stop6h 40m

Aspen Pitkin County

Mon 4/6

3:00 pm-10:31 pm

1 stop6h 31m

$1,085

ChicagoAspen

MDW - ASE

MDWASE

Chicago Midway

Fri 2/6

6:00 am-11:43 am

1 stop6h 43m

Aspen Pitkin County

Mon 2/9

1:34 pm-10:22 pm

1 stop7h 48m

$1,179

ChicagoAspen

MDW - ASE

MDWASE

Chicago Midway

Sat 2/28

6:00 am-2:14 pm

1 stop9h 14m

Aspen Pitkin County

Tue 3/3

3:00 pm-10:33 pm

1 stop6h 33m

$1,179

ChicagoAspen

MDW - ASE

MDWASE

Chicago Midway

Thu 2/5

6:00 am-11:43 am

1 stop6h 43m

Aspen Pitkin County

Tue 2/10

3:04 pm-10:22 pm

1 stop6h 18m

$1,215

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/19

Showing 1-10 of 18 results
1
2

Compare providers for flights from Midway to Aspen

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Midway to Aspen in January.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Chicago Midway Airport-Aspen flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago Midway Airport-Aspen flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago Midway Airport-Aspen flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago Midway Airport-Aspen flights, Cheapflights users trust Expedia the most. Expedia 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 Chicago Midway Airport-Aspen 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 Midway to Aspen

Have a flexible travel schedule? Discover the best time to fly to Aspen from Midway 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.

Related info for your journey

Find useful and relevant information for your journey from Midway to Aspen. 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 into for flights to Aspen from Chicago Midway?

    Located just 3.5 mi from the city center, Aspen Pitkin County is the airport most travelers will use when flying to Aspen from Chicago Midway. Booking flights from Chicago Midway to Pitkin County (ASE) should be relatively easy as there are 0 daily inbound flights from Chicago Midway from 0 different airlines.

  • How long is the flight from Chicago Midway Airport to Aspen?

    Delta can get you from Chicago Midway Airport to Aspen in just under 9h 16m. Your travel time can differ by up to . The distance from Chicago Midway Airport to Aspen is about 1017 mi.

  • Can I find deals for flights from Midway to Aspen that include hotel bookings?

    Yes. In addition to deals on Midway to Aspen flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Midway to Aspen?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Midway to Aspen.

  • Can I find deals for business class flights from Midway to Aspen?

    Yes. Cheapflights offers flight deals from Midway to Aspen by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

See more FAQs

Traveling to a place near Aspen?

Book flights to Aspen if you plan to visit one of these locations
Snowmass Village
Buena Vista
Snowmass

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