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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 12/8. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — ASE
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
1 adult, Economy
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Cheap 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 September 11, 2025.

Round-trip from

$494
(Delta)

One-way from

$221
(Delta)

Popular in

November

Cheapest in

September

Average price

$414
From Chicago Midway to Aspen Pitkin County
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One-way flight from Chicago Midway to Aspen Pitkin County
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Highest demand for flights based on searches. 6% potential increase in price ($35 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($10 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find 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 September 11, 2025.

This Delta deal was found by Cheapflights users on 9/11. 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 10/126:00 amMDW - ASE
1 stop6h 10mDelta
Sun 10/197:21 amASE - MDW
1 stop7h 48mDelta
Deal found 9/11$494
This Delta deal was found by Cheapflights users on 9/11. 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 12/176:00 amMDW - ASE
1 stop6h 35mDelta
Sun 12/212:55 pmASE - MDW
1 stop6h 21mDelta
Deal found 9/11$539
This Delta deal was found by Cheapflights users on 9/10. 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 10/126:00 amMDW - ASE
1 stop6h 10mDelta
Thu 10/167:21 amASE - MDW
2 stops10h 04mDelta
Deal found 9/10$680
This Delta deal was found by Cheapflights users on 9/11. 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.
Tue 9/166:00 amMDW - ASE
1 stop6h 13mDelta
Sat 9/207:16 amASE - MDW
2 stops10h 19mDelta
Deal found 9/11$924
This Delta deal was found by Cheapflights users on 9/11. 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 9/196:00 amMDW - ASE
1 stop6h 13mDelta
Tue 9/237:16 amASE - MDW
2 stops10h 19mDelta
Deal found 9/11$954
This Delta deal was found by Cheapflights users on 9/10. 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.
Thu 10/96:00 amMDW - ASE
1 stop6h 10mDelta
Sun 10/127:21 amASE - MDW
1 stop7h 48mDelta
Deal found 9/10$1,080
This Delta deal was found by Cheapflights users on 9/10. 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 10/106:00 amMDW - ASE
1 stop6h 10mDelta
Fri 10/177:21 amASE - MDW
2 stops9h 22mDelta
Deal found 9/10$1,184
This Delta deal was found by Cheapflights users on 9/11. 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 9/246:00 amMDW - ASE
1 stop6h 13mDelta
Sat 9/277:16 amASE - MDW
1 stop7h 10mDelta
Deal found 9/11$1,339
This Delta deal was found by Cheapflights users on 9/10. 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 9/206:00 amMDW - ASE
1 stop6h 13mDelta
Fri 9/267:16 amASE - MDW
2 stops10h 19mDelta
Deal found 9/10$1,344

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 September 11, 2025.
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 10/12

6:00 am-11:10 am

1 stop6h 10m

Aspen Pitkin County

Sun 10/19

7:21 am-4:09 pm

1 stop7h 48m

$494

ChicagoAspen

MDW - ASE

MDWASE

Chicago Midway

Wed 12/17

6:00 am-11:35 am

1 stop6h 35m

Aspen Pitkin County

Sun 12/21

2:55 pm-10:16 pm

1 stop6h 21m

$539

ChicagoAspen

MDW - ASE

MDWASE

Chicago Midway

Sun 10/12

6:00 am-11:10 am

1 stop6h 10m

Aspen Pitkin County

Thu 10/16

7:21 am-6:25 pm

2 stops10h 04m

$680

ChicagoAspen

MDW - ASE

MDWASE

Chicago Midway

Thu 1/8

6:00 am-2:19 pm

1 stop9h 19m

Aspen Pitkin County

Mon 1/12

1:50 pm-9:46 pm

1 stop6h 56m

$919

ChicagoAspen

MDW - ASE

MDWASE

Chicago Midway

Wed 1/14

6:00 am-2:19 pm

1 stop9h 19m

Aspen Pitkin County

Tue 1/20

1:50 pm-9:46 pm

1 stop6h 56m

$949

ChicagoAspen

MDW - ASE

MDWASE

Chicago Midway

Fri 2/20

6:00 am-2:19 pm

1 stop9h 19m

Aspen Pitkin County

Tue 2/24

1:50 pm-9:46 pm

1 stop6h 56m

$1,040

ChicagoAspen

MDW - ASE

MDWASE

Chicago Midway

Thu 10/9

6:00 am-11:10 am

1 stop6h 10m

Aspen Pitkin County

Sun 10/12

7:21 am-4:09 pm

1 stop7h 48m

$1,080

ChicagoAspen

MDW - ASE

MDWASE

Chicago Midway

Fri 10/10

6:00 am-11:10 am

1 stop6h 10m

Aspen Pitkin County

Fri 10/17

7:21 am-5:43 pm

2 stops9h 22m

$1,184

ChicagoAspen

MDW - ASE

MDWASE

Chicago Midway

Thu 1/29

6:00 am-11:49 am

1 stop6h 49m

Aspen Pitkin County

Sun 2/1

1:50 pm-9:46 pm

1 stop6h 56m

$1,339

ChicagoAspen

MDW - ASE

MDWASE

Chicago Midway

Mon 12/8

6:00 am-11:35 am

1 stop6h 35m

$221

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/11

Showing 1-10 of 15 results
1
2

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 10m. 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.

  • What is the cheapest month to book a flight from Chicago Midway Airport to Aspen?

    Currently, November is the cheapest month in which you can book a flight from Chicago Midway Airport to Aspen (average of $448). Flying from Chicago Midway Airport to Aspen in December is currently the most expensive (average of $662). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Aspen?

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

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