$120 Cheap Flights from Chicago (MDW) to Aspen (ASE)

View $120 flight on Tue, Sep 9, 2025Opens 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 to Aspen (MDW-ASE)

Prices were available within the past 7 days and start at $120 for one-way flights and $217 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Mon, Oct 6 - Tue, Oct 21
MDW
Chicago
ASE
Aspen
$217 Roundtrip, found 10 hours ago
$217
Roundtrip
found 10 hours ago
Select Delta flight, departing Mon, Oct 6 from Chicago to Aspen, returning Tue, Oct 21, priced at $217 found 10 hours ago
Delta
Tue, Sep 9 - Wed, Sep 24
MDW
Chicago
ASE
Aspen
$231 Roundtrip, found 2 days ago
$231
Roundtrip
found 2 days ago
Select Delta flight, departing Tue, Sep 9 from Chicago to Aspen, returning Wed, Sep 24, priced at $231 found 2 days ago
Delta
Tue, Sep 9 - Sat, Sep 13
MDW
Chicago
ASE
Aspen
$233 Roundtrip, found 1 hour ago
$233
Roundtrip
found 1 hour ago
Select Delta flight, departing Tue, Sep 9 from Chicago to Aspen, returning Sat, Sep 13, priced at $233 found 1 hour ago
Delta
Tue, Sep 9 - Sat, Sep 13
MDW
Chicago
ASE
Aspen
$240 Roundtrip, found 2 days ago
$240
Roundtrip
found 2 days ago
Select Delta flight, departing Tue, Sep 9 from Chicago to Aspen, returning Sat, Sep 13, priced at $240 found 2 days ago
Delta
Sat, Sep 20 - Sat, Sep 27
MDW
Chicago
ASE
Aspen
$249 Roundtrip, found 10 hours ago
$249
Roundtrip
found 10 hours ago
Select Delta flight, departing Sat, Sep 20 from Chicago to Aspen, returning Sat, Sep 27, priced at $249 found 10 hours ago
Delta
Tue, Sep 9 - Sat, Sep 27
MDW
Chicago
ASE
Aspen
$255 Roundtrip, found 2 days ago
$255
Roundtrip
found 2 days ago
Select Delta flight, departing Tue, Sep 9 from Chicago to Aspen, returning Sat, Sep 27, priced at $255 found 2 days ago
Delta
Mon, Oct 20 - Wed, Nov 5
MDW
Chicago
ASE
Aspen
$256 Roundtrip, found 4 days ago
$256
Roundtrip
found 4 days ago
Select Delta flight, departing Mon, Oct 20 from Chicago to Aspen, returning Wed, Nov 5, priced at $256 found 4 days ago
Delta
Sun, Oct 19 - Wed, Nov 5
MDW
Chicago
ASE
Aspen
$259 Roundtrip, found 10 hours ago
$259
Roundtrip
found 10 hours ago
Select Delta flight, departing Sun, Oct 19 from Chicago to Aspen, returning Wed, Nov 5, priced at $259 found 10 hours ago
Delta
Mon, Oct 20 - Tue, Nov 4
MDW
Chicago
ASE
Aspen
$261 Roundtrip, found 4 days ago
$261
Roundtrip
found 4 days ago
Select Delta flight, departing Mon, Oct 20 from Chicago to Aspen, returning Tue, Nov 4, priced at $261 found 4 days ago
Delta
Sat, Sep 20 - Wed, Sep 24
MDW
Chicago
ASE
Aspen
$264 Roundtrip, found 10 hours ago
$264
Roundtrip
found 10 hours ago
Select Delta flight, departing Sat, Sep 20 from Chicago to Aspen, returning Wed, Sep 24, priced at $264 found 10 hours ago
Flights from Chicago (MDW) to Aspen (ASE)
Origin airport
Midway Intl.
Destination airport
Pitkin County
Airlines serving
Delta
Roundtrip price
$216
Distance
1017 mi

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 $120 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.

 

Frequently asked questions

How much does a flight from Midway Intl. Airport (MDW) to Pitkin County Airport (ASE) cost?
Discover the latest flight deals from MDW to ASE by entering your preferred travel dates and searching on Expedia. Easily compare prices by departure date if you have flexibility with your schedule and use handy filters to explore prices for your preferred journey. As a member of One Key™, our free loyalty program, you can use Price Tracking to watch fares and receive notifications if prices go up or down.
What is the cheapest month to fly from MDW to ASE?
The cheapest flights from MDW to ASE are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
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 MDW to ASE?
Use the filter tool on Expedia to compare airlines and find the cheapest carrier that'll take you from MDW to ASE. Sort your results by "Price (lowest to highest)" to snap up a great deal.
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.

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*Available to One Key members.