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$182+ 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 7/21. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — ASE
Jul 11 — Jul 181
Sat 7/11
Sat 7/18
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 June 11, 2026.

This Delta deal was found by Cheapflights users on 6/9. 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 8/106:05 am
MDW
-
ASE
1 stop6h 18m
Delta
Thu 8/137:20 am
ASE
-
MDW
1 stop7h 55m
Delta
Deal found 6/9$363
This Delta deal was found by Cheapflights users on 6/8. 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.
Sat 11/76:00 am
MDW
-
ASE
1 stop6h 35m
Delta
Tue 11/101:50 pm
ASE
-
MDW
1 stop7h 20m
Delta
Deal found 6/8$421
This Delta deal was found by Cheapflights users on 6/9. 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.
Fri 10/306:00 am
MDW
-
ASE
1 stop6h 35m
Delta
Tue 11/38:05 am
ASE
-
MDW
2 stops9h 32m
Delta
Deal found 6/9$426
This Delta deal was found by Cheapflights users on 6/9. 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 11/46:00 am
MDW
-
ASE
1 stop6h 35m
Delta
Sun 11/88:05 am
ASE
-
MDW
1 stop7h 20m
Delta
Deal found 6/9$479
This Delta deal was found by Cheapflights users on 6/7. 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.
Fri 9/116:00 am
MDW
-
ASE
1 stop6h 21m
Delta
Mon 9/147:30 am
ASE
-
MDW
1 stop7h 41m
Delta
Deal found 6/7$549
This Delta deal was found by Cheapflights users on 6/9. 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 7/126:00 am
MDW
-
ASE
1 stop6h 22m
Delta
Tue 7/217:30 am
ASE
-
MDW
1 stop7h 45m
Delta
Deal found 6/9$744

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 June 11, 2026.

Most accurate provider

Expedia
1 star

Most trusted provider

Expedia
3 stars

Round-trip from

$363
(Delta)

One-way from

$182
(Delta)

Popular in

January

Cheapest in

September

Average price

$480
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. 17% potential increase in price ($99 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($16 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in June 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 June 11, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Aspen that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoAspen

MDW - ASE

MDWASE

Chicago Midway

Sat 7/11

6:00 am-11:22 am

1 stop6h 22m

Aspen Pitkin County

Tue 7/14

7:30 am-6:25 pm

2 stops9h 55m

$1,149

ChicagoAspen

MDW - ASE

MDWASE

Chicago Midway

Wed 7/1

6:00 am-11:23 am

1 stop6h 23m

Aspen Pitkin County

Wed 7/8

7:30 am-4:15 pm

1 stop7h 45m

$1,399

ChicagoAspen

MDW - ASE

MDWASE

Chicago Midway

Thu 9/3

6:05 am-11:23 am

1 stop6h 18m

Aspen Pitkin County

Mon 9/7

7:20 am-4:15 pm

1 stop7h 55m

$1,549

ChicagoAspen

MDW - ASE

MDWASE

Chicago Midway

Tue 7/28

6:00 am-11:22 am

1 stop6h 22m

Aspen Pitkin County

Fri 7/31

7:30 am-4:15 pm

1 stop7h 45m

$1,583

ChicagoAspen

MDW - ASE

MDWASE

Chicago Midway

Wed 8/26

6:05 am-11:23 am

1 stop6h 18m

Aspen Pitkin County

Sun 8/30

7:20 am-4:15 pm

1 stop7h 55m

$1,640

ChicagoAspen

MDW - ASE

MDWASE

Chicago Midway

Fri 7/10

6:00 am-11:22 am

1 stop6h 22m

Aspen Pitkin County

Mon 7/13

7:30 am-6:18 pm

2 stops9h 48m

$1,746
Quickest round-trip

ChicagoAspen

MDW - ASE

MDWASE

Chicago Midway

Sun 6/21

6:00 am-11:23 am

1 stop6h 23m

Aspen Pitkin County

Wed 6/24

7:36 am-4:16 pm

1 stop7h 40m

$1,789

ChicagoAspen

MDW - ASE

MDWASE

Chicago Midway

Mon 6/22

6:00 am-11:23 am

1 stop6h 23m

Aspen Pitkin County

Thu 6/25

7:36 am-4:16 pm

1 stop7h 40m

$1,961

ChicagoAspen

MDW - ASE

MDWASE

Chicago Midway

Wed 6/24

6:00 am-11:23 am

1 stop6h 23m

Aspen Pitkin County

Fri 6/26

7:36 am-6:31 pm

2 stops9h 55m

$2,006
Cheapest one-way
Quickest one-way

ChicagoAspen

MDW - ASE

MDWASE

Chicago Midway

Tue 7/21

6:00 am-11:22 am

1 stop6h 22m

$182

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/9

Showing 1-10 of 17 resultsSorted by cheapest first
1
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  • Most accurate provider: When it comes to deals on Chicago Midway Airport-Aspen flights, users find the pricing of Expedia to be most consistent on Cheapflights vs. Expedia Users can find the same prices on Chicago Midway Airport-Aspen flight deals on Cheapflights vs. Expedia <90% 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 6h 22m. 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
Leadville
Buena Vista
Snowmass

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