$137 Cheap Flights from Chicago (MDW) to Aspen (ASE)

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Cheap Flights from Chicago to Aspen (MDW-ASE)

Prices were available within the past 7 days and start at $137 for one-way flights and $269 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Tue, Oct 21 - Sat, Nov 1
MDW
Chicago
ASE
Aspen
$269 Roundtrip, found 2 days ago
$269
Roundtrip
found 2 days ago
Select Delta flight, departing Tue, Oct 21 from Chicago to Aspen, returning Sat, Nov 1, priced at $269 found 2 days ago
Delta
Wed, Oct 15 - Tue, Nov 4
MDW
Chicago
ASE
Aspen
$274 Roundtrip, found 6 days ago
$274
Roundtrip
found 6 days ago
Select Delta flight, departing Wed, Oct 15 from Chicago to Aspen, returning Tue, Nov 4, priced at $274 found 6 days ago
Delta
Sat, Oct 11 - Wed, Oct 22
MDW
Chicago
ASE
Aspen
$284 Roundtrip, found 23 hours ago
$284
Roundtrip
found 23 hours ago
Select Delta flight, departing Sat, Oct 11 from Chicago to Aspen, returning Wed, Oct 22, priced at $284 found 23 hours ago
Delta
Sat, Nov 1 - Tue, Nov 4
MDW
Chicago
ASE
Aspen
$309 Roundtrip, found 4 hours ago
$309
Roundtrip
found 4 hours ago
Select Delta flight, departing Sat, Nov 1 from Chicago to Aspen, returning Tue, Nov 4, priced at $309 found 4 hours ago
Delta
Wed, Dec 24 - Mon, Dec 29
MDW
Chicago
ASE
Aspen
$314 Roundtrip, found 13 hours ago
$314
Roundtrip
found 13 hours ago
Select Delta flight, departing Wed, Dec 24 from Chicago to Aspen, returning Mon, Dec 29, priced at $314 found 13 hours ago
Delta
Sat, Nov 8 - Tue, Nov 11
MDW
Chicago
ASE
Aspen
$317 Roundtrip, found 1 day ago
$317
Roundtrip
found 1 day ago
Select Delta flight, departing Sat, Nov 8 from Chicago to Aspen, returning Tue, Nov 11, priced at $317 found 1 day ago
Delta
Sat, Oct 11 - Fri, Oct 24
MDW
Chicago
ASE
Aspen
$329 Roundtrip, found 23 hours ago
$329
Roundtrip
found 23 hours ago
Select Delta flight, departing Sat, Oct 11 from Chicago to Aspen, returning Fri, Oct 24, priced at $329 found 23 hours ago
Delta
Mon, Oct 27 - Sat, Nov 8
MDW
Chicago
ASE
Aspen
$337 Roundtrip, found 6 days ago
$337
Roundtrip
found 6 days ago
Select Delta flight, departing Mon, Oct 27 from Chicago to Aspen, returning Sat, Nov 8, priced at $337 found 6 days ago
Delta
Thu, Oct 23 - Sat, Nov 8
MDW
Chicago
ASE
Aspen
$344 Roundtrip, found 6 days ago
$344
Roundtrip
found 6 days ago
Select Delta flight, departing Thu, Oct 23 from Chicago to Aspen, returning Sat, Nov 8, priced at $344 found 6 days ago
Delta
Fri, Oct 17 - Tue, Nov 4
MDW
Chicago
ASE
Aspen
$349 Roundtrip, found 6 days ago
$349
Roundtrip
found 6 days ago
Select Delta flight, departing Fri, Oct 17 from Chicago to Aspen, returning Tue, Nov 4, priced at $349 found 6 days ago

Frequently asked questions

How much does a flight from Midway Intl. Airport (MDW) to Pitkin County Airport (ASE) cost?
Get a cheap one-way flight from $137 or cheap return flight from $269 from Midway Intl. Airport (MDW) to Pitkin County Airport (ASE) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to see our cheapest flight deals on this route.
What is the cheapest month to fly from Midway Intl. Airport (MDW) to Pitkin County Airport (ASE)?
October is the most affordable month to fly from MDW to ASE. Planning your trip for the off-season is often the key to finding better fares.
Which airlines fly direct from Midway Intl. Airport (MDW) to Pitkin County Airport (ASE)?
While Chicago, IL (MDW-Midway Intl.) doesn't offer any direct flights to Pitkin County Airport (ASE), other airports have nonstop routes. Leaving from O'Hare Intl. Airport (ORD) will get you to Aspen without any detours.
What is the cheapest airline that flies from Midway Intl. Airport (MDW) to Pitkin County Airport (ASE)?
Use the filter tool on Expedia to compare airlines and find the most affordable carrier that'll fly you from MDW to ASE. Then, sort your results by "Price (lowest to highest)" to score the best deal available.
How many flights per day from Midway Intl. Airport (MDW) to Pitkin County Airport (ASE)?
Direct flights from Midway Intl. Airport (MDW) to Pitkin County Airport (ASE) aren't available daily, so you'll need to take a flight with a layover. Explore your options with our filter tool. Enter your dates and pick either "1 Stop" or "2+ Stops."
What day of the week has the most flights from MDW to ASE?
You'll generally find Tuesday the quietest day for flights, while Fridays tend to be the busiest.* However this can vary from season to season and during peak travel times or public holidays.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Midway Intl. Airport (MDW) to Pitkin County Airport (ASE)?
To arrive at Pitkin County Airport (ASE) on time, choose a flight that leaves from Midway Intl. Airport (MDW) before 3 PM. The likelihood of cancellations is 22% higher, on average, for departures after this hour.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
Is it cheaper to buy a plane ticket from Midway Intl. Airport (MDW) to Pitkin County Airport (ASE) last-minute?
Booking your ticket from MDW to ASE shortly before your journey is usually more expensive. However, if there's some wiggle room with your schedule, you could land a cheap last-minute fare.
Is it cheaper to book a MDW to ASE flight and hotel package?
You'll typically save money by booking a MDW to ASE flight and hotel package compared to booking separately. In fact, travelers could save hundreds of dollars by bundling with Expedia. And it's easy to manage it all in one place. After selecting your ideal accommodations and flights, consider adding extras like car rentals, tours and activities.
Can I cancel or change the date of my flight from Midway Intl. Airport (MDW) to Pitkin County Airport (ASE)?
In most cases, you can cancel or reschedule your MDW to ASE flight. However, additional fees may apply, especially if you made your booking more than 24 hours ago. Check your itinerary for the airline's fees and guidelines on flight changes, or if you need more information, visit our Customer Service portal.

Travel information

Travel information

Origin airport
Midway Intl.
Destination airport
Pitkin County
Airlines serving
Delta
Roundtrip price
$268
Distance
1017 mi

Book with confidence

Book with confidence

Chicago to Aspen Flights

The cheapest times to fly from Chicago to Aspen

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Chicago to Aspen are during the month of October. You can find some of the cheapest flights from Chicago to Aspen with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Chicago to Aspen

Sunday is one of the best days to book for cheap flights from Chicago to Aspen: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Chicago to Aspen

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Chicago to Aspen in 2025. You can also book with separate airlines for your outbound and return journeys, from $137 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Chicago to Aspen flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Chicago to Aspen airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Chicago to Aspen Flights

Explore a world of travel with Expedia

Explore a world of travel with Expedia

*Available to One Key members.