CA $394 Cheap Flights from Chicago (MDW) to Aspen (ASE)

View CA $394 flight on Fri, Apr 10, 2026Opens in a new window

Popular airlines from Chicago Midway Airport (MDW) to Aspen/Pitkin County Airport (ASE)

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Cheap flights from Chicago (MDW) to Aspen (ASE)

Prices were available within the past 7 days and start at CA $394 for one-way flights and CA $544 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Tue, Apr 7 - Wed, Apr 15
MDW
Chicago
ASE
Aspen
CA $544 Roundtrip, found 3 days ago
CA $544
Roundtrip
found 3 days ago
Select Delta flight, departing Tue, Apr 7 from Chicago to Aspen, returning Wed, Apr 15, priced at CA $544 found 3 days ago
Delta
Wed, Apr 8 - Wed, Apr 15
MDW
Chicago
ASE
Aspen
CA $576 Roundtrip, found 3 days ago
CA $576
Roundtrip
found 3 days ago
Select Delta flight, departing Wed, Apr 8 from Chicago to Aspen, returning Wed, Apr 15, priced at CA $576 found 3 days ago
Delta
Mon, Apr 13 - Wed, Apr 15
MDW
Chicago
ASE
Aspen
CA $605 Roundtrip, found 3 days ago
CA $605
Roundtrip
found 3 days ago
Select Delta flight, departing Mon, Apr 13 from Chicago to Aspen, returning Wed, Apr 15, priced at CA $605 found 3 days ago
Delta
Thu, Apr 9 - Fri, Apr 17
MDW
Chicago
ASE
Aspen
CA $644 Roundtrip, found 3 days ago
CA $644
Roundtrip
found 3 days ago
Select Delta flight, departing Thu, Apr 9 from Chicago to Aspen, returning Fri, Apr 17, priced at CA $644 found 3 days ago
Delta
Fri, Apr 10 - Tue, Apr 14
MDW
Chicago
ASE
Aspen
CA $1,359 Roundtrip, found 3 days ago
CA $1,359
Roundtrip
found 3 days ago
Select Delta flight, departing Fri, Apr 10 from Chicago to Aspen, returning Tue, Apr 14, priced at CA $1,359 found 3 days ago
Delta
Fri, Apr 10 - Tue, Apr 14
MDW
Chicago
ASE
Aspen
CA $1,562 Roundtrip, found 3 days ago
CA $1,562
Roundtrip
found 3 days ago
Select Delta flight, departing Fri, Apr 10 from Chicago to Aspen, returning Tue, Apr 14, priced at CA $1,562 found 3 days ago
Delta
Fri, Apr 10 - Tue, Apr 14
MDW
Chicago
ASE
Aspen
CA $1,563 Roundtrip, found 3 days ago
CA $1,563
Roundtrip
found 3 days ago
Select Delta flight, departing Fri, Apr 10 from Chicago to Aspen, returning Tue, Apr 14, priced at CA $1,563 found 3 days ago

Frequently asked questions

How much is a flight from MDW to Aspen/Pitkin County Airport?
Round-trip tickets from Midway Airport to Aspen/Pitkin County Airport start from CA $544. This is based on fares quoted within the last 7 days on Expedia for flights departing within the next year — book today to avoid missing out. Prices and availability are subject to change. Additional terms apply.
Do I need to pay a cancellation fee if I cancel my flight from Midway Intl. Airport (MDW) to Pitkin County Airport (ASE)?
Most flights can be cancelled online, but whether you are charged a fee varies between airlines. If you do need to cancel your break, follow the instructions in the Customer Service Portal.
How do I find cheap flights from Midway Intl. Airport (MDW) to Pitkin County Airport (ASE) that have flexible change policies?
Many airlines will allow you to move your flight without a change fee. All you pay is the cost difference between flights. When searching for Chicago Airport to Aspen/Pitkin County Airport flights, you'll find a "No change fees" filter for you to pick.
How many hours is the flight from Midway Airport to ASE?
The flight time from MDW to Pitkin County Airport (ASE) is around 5 hours and 56 minutes. Put on your earphones, listen to a good podcast and the hours will fly by.
How far is the flight from Midway Intl. Airport (MDW) to Aspen/Pitkin County Airport?
The flight distance from Midway Airport to Pitkin County Airport (ASE) is 1,650 kilometres. Bring along a drink, a snack and an interesting novel to read. Keep yourself occupied and time will zip by.
Which airlines fly direct from MDW to Pitkin County Airport (ASE)?
Unfortunately, there are no airlines that fly directly between Midway Intl. Airport (MDW) and Aspen/Pitkin County Airport. You'll have to book a flight with at least one stop.
Are Chicago Airport to Aspen/Pitkin County Airport flight tickets cheaper when they're purchased at the last minute?
Last-minute planners can occasionally score a bargain, with some super cheap fares from Midway Intl. Airport (MDW) to Pitkin County Airport (ASE) cropping up a few weeks before the date of departure. If you'd rather book ahead, Expedia compares and updates all the best flight deals continually — as early as 12 months in advance in some cases. It depends on the carrier though, as not all airlines publish prices that far in advance.

Travel information

Origin airport
Midway Intl.
Destination airport
Pitkin County
Roundtrip price
CA $544
Distance
1628 km

Book with confidence

Chicago to Aspen Flights

The easy way to book your flights from Chicago to Aspen 

With Expedia, it’s simple to find and book flights to Aspen from Chicago whether you’re traveling for business or pleasure. Enter your travel dates, hit search, and choose your flight from 10 airlines that cover this route. There are nonstop flights to Pitkin County, too.  

Choose your preferred carrier and cabin class with the advanced search tool and select your ideal departure time. Then, if you want, you can see just nonstop or refundable flights. And if you’re traveling last minute, just enter the date to check out flights from Chicago to Aspen today, tomorrow, or this week.  

 

Save dollars with cheap flights from Midway Intl., MDW to Pitkin County, ASE 

Sort your search results by price to find great deals on your flight from Chicago to Aspen—you get all your cheapest options first. Grab yourself a bargain now—the lowest price on flights to Aspen from Chicago currently is just CA $544 rising to CA $1,563.  

Here are more money-saving tips: 

  • Fly in April when flight prices are normally at their lowest 
  • Book about a month to 6 weeks before you travel for the best prices to Aspen  
  • Avoid peak season and weekends when flights can cost more
  • Early morning and late-night flights are sometimes cheaper, so try varying your travel times 
  • One surefire way to save money on your flight is to book your flight and hotel together with Expedia. Sometimes, the savings are so large that the flight is basically free! 

 

Reasons to choose Expedia for your flight to Aspen from Chicago 

Whatever your destination, budget, or reason to travel, in just one quick search, you can choose from loads of flights, airlines, and cabin classes. The filters make it quick and easy to find your ideal flights, and if you choose one of the flexible options, you won’t be charged to change your flight. So book your flight to Aspen with Expedia today.

Chicago to Aspen Flights
*Available to Expedia members.