Cheap Flights from Chicago (PWK) to Aspen (ASE)

Popular airlines from Chicago, IL (PWK-Chicago Executive) to Aspen/Pitkin County Airport (ASE)

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Frequently asked questions

How much does a flight from Chicago Executive Airport (PWK) to Pitkin County Airport (ASE) cost?
Lock in a cheap one-way flight or cheap return flight from Chicago Executive Airport (PWK) to Pitkin County Airport (ASE) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight deals on this route.
What is the cheapest month to fly from Chicago Executive Airport (PWK) to Pitkin County Airport (ASE)?
The cheapest month to fly from PWK to ASE is , when there's less demand. Off-peak months are typically when airlines offer lower prices between these airports.
Which airlines fly direct from Chicago Executive Airport (PWK) to Pitkin County Airport (ASE)?
While Chicago, IL (PWK-Chicago Executive) doesn't have any direct flights to Pitkin County Airport (ASE), other airports have nonstop routes. Flying from O'Hare Intl. Airport (ORD) will get you to Aspen without any detours.
What is the cheapest airline that flies from Chicago Executive Airport (PWK) to Pitkin County Airport (ASE)?
Expedia's filter tool lets you easily compare different airlines, travel time and fares all in one place. Choose your preferences, then sort by "Price (lowest to highest)" to see which carrier offers the cheapest PWK to ASE flight.
How many flights per day from Chicago Executive Airport (PWK) to Pitkin County Airport (ASE)?
There are no daily nonstop flights available from Chicago Executive Airport (PWK) to Pitkin County Airport (ASE). But you can book flights with layovers. Filter your search on Expedia to include one or more stops, and you'll be on your way in no time at all.
What day of the week has the most flights from PWK to ASE?
Generally you'll have the most choice when it comes to flights on a Friday. Tuesdays are often the quietest.* However, this can vary based on the time of year, carrier and other factors.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Chicago Executive Airport (PWK) to Pitkin County Airport (ASE)?
To avoid potential delays on the Chicago Executive Airport (PWK) to Pitkin County Airport (ASE) route, aim to fly before 3 PM. Later flights have a 22% higher chance of being canceled.**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 Chicago Executive Airport (PWK) to Pitkin County Airport (ASE) last-minute?
Last-minute fares from PWK to ASE are usually more expensive. To lock in the lowest rates, start searching for flights as soon as possible. That being said, if you're flexible with your travel plans, you may land a cheap fare right before your trip.
Is it cheaper to book a PWK to ASE flight and hotel package?
You'll typically save money by securing a PWK 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 convenient place. Once you've selected your preferred flights and accommodations, you can add extras like tours, activities and car rentals.
Can I cancel or change the date of my flight from Chicago Executive Airport (PWK) to Pitkin County Airport (ASE)?
If you booked your PWK to ASE flight in the last 24 hours, you may be able to cancel or modify it at no cost. Depending on the airline and the fare type you purchased, additional charges may apply for changes beyond that time. Airline policies and contact information can be found in your itinerary or confirmation email. Or, head to our Customer Service portal for more details.

Travel information

Travel information

Origin airport
Chicago Executive
Destination airport
Pitkin County
Distance
1011 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 . 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 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

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*Available to One Key members.