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$334+ Cheap flights from Midway (MDW) to Aspen (ASE)

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 9/9. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — ASE
ago. 2 — ago. 91
sáb. 8/2
sáb. 8/9
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 julio 28, 2025.

Round-trip from

$334
(Delta)

Popular in

November

Cheapest in

August

Average price

$521
From Chicago Midway to Aspen Pitkin County
Search Deals
Highest demand for flights based on searches. 14% potential increase in price ($94 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease ($30 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 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 julio 28, 2025.

This Delta deal was found by Cheapflights users on 7/26. 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.
mar. 9/96:00 amMDW - ASE
1 stop6h 21mDelta
mar. 9/167:16 amASE - MDW
2 stops10h 19mDelta
Deal found 7/26$334

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 julio 28, 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

mar. 9/9

6:00 am-11:21 am

1 stop6h 21m

Aspen Pitkin County

mar. 9/16

7:16 am-6:35 pm

2 stops10h 19m

$334

ChicagoAspen

MDW - ASE

MDWASE

Chicago Midway

dom. 8/3

6:00 am-11:21 am

1 stop6h 21m

$340

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/27

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.

Reviews of airlines servicing Aspen

Get insights into the airlines that provide service to Aspen. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Aspen. Reviews last updated julio 28, 2025.
See what other customers who have flown with Delta from Chicago Midway Airport to Aspen have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,971 reviews

Boarding

8.2

Crew

8.5

Entertainment

7.9

Overall

8.0

Food

7.3

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Delta
8.0
Very good
7,971 reviews
Delta
8.0
Very good
7,971 reviews

Boarding

8.2

Crew

8.5

Entertainment

7.9

Overall

8.0

Food

7.3

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

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.

  • 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 $667). 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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