$110 Cheap Flights from Chicago (ORD) to Aspen (ASE)

View $110 flight on Sun, Sep 28, 2025Opens in a new window

Popular airlines from Chicago O'Hare Intl. Airport (ORD) to Aspen/Pitkin County Airport (ASE)

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Cheap Flights from Chicago to Aspen (ORD-ASE)

Prices were available within the past 7 days and start at $110 for one-way flights and $191 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

American Airlines
Sun, Sep 28 - Wed, Oct 1
ORD
Chicago
ASE
Aspen
$191 Roundtrip, found 1 hour ago
$191
Roundtrip
found 1 hour ago
Select American Airlines flight, departing Sun, Sep 28 from Chicago to Aspen, returning Wed, Oct 1, priced at $191 found 1 hour ago
United
Tue, Sep 16 - Fri, Sep 19
ORD
Chicago
ASE
Aspen
$201 Roundtrip, found 2 days ago
$201
Roundtrip
found 2 days ago
Select United flight, departing Tue, Sep 16 from Chicago to Aspen, returning Fri, Sep 19, priced at $201 found 2 days ago
American Airlines
Sun, Sep 28 - Wed, Oct 1
ORD
Chicago
ASE
Aspen
$211 Roundtrip, found 1 hour ago
$211
Roundtrip
found 1 hour ago
Select American Airlines flight, departing Sun, Sep 28 from Chicago to Aspen, returning Wed, Oct 1, priced at $211 found 1 hour ago
United
Tue, Sep 16 - Thu, Sep 18
ORD
Chicago
ASE
Aspen
$216 Roundtrip, found 5 days ago
$216
Roundtrip
found 5 days ago
Select United flight, departing Tue, Sep 16 from Chicago to Aspen, returning Thu, Sep 18, priced at $216 found 5 days ago
United
Mon, Sep 29 - Fri, Oct 3
ORD
Chicago
ASE
Aspen
$218 Roundtrip, found 6 days ago
$218
Roundtrip
found 6 days ago
Select United flight, departing Mon, Sep 29 from Chicago to Aspen, returning Fri, Oct 3, priced at $218 found 6 days ago
United
Fri, Oct 10 - Wed, Oct 15
ORD
Chicago
ASE
Aspen
$220 Roundtrip, found 2 hours ago
$220
Roundtrip
found 2 hours ago
Select United flight, departing Fri, Oct 10 from Chicago to Aspen, returning Wed, Oct 15, priced at $220 found 2 hours ago
Delta
Tue, Oct 28 - Tue, Nov 4
ORD
Chicago
ASE
Aspen
$222 Roundtrip, found 3 days ago
$222
Roundtrip
found 3 days ago
Select Delta flight, departing Tue, Oct 28 from Chicago to Aspen, returning Tue, Nov 4, priced at $222 found 3 days ago
United
Tue, Sep 16 - Thu, Sep 18
ORD
Chicago
ASE
Aspen
$226 Roundtrip, found 5 days ago
$226
Roundtrip
found 5 days ago
Select United flight, departing Tue, Sep 16 from Chicago to Aspen, returning Thu, Sep 18, priced at $226 found 5 days ago
Delta
Mon, Nov 17 - Tue, Dec 9
ORD
Chicago
ASE
Aspen
$228 Roundtrip, found 4 days ago
$228
Roundtrip
found 4 days ago
Select Delta flight, departing Mon, Nov 17 from Chicago to Aspen, returning Tue, Dec 9, priced at $228 found 4 days ago
United
Mon, Sep 29 - Fri, Oct 3
ORD
Chicago
ASE
Aspen
$229 Roundtrip, found 6 days ago
$229
Roundtrip
found 6 days ago
Select United flight, departing Mon, Sep 29 from Chicago to Aspen, returning Fri, Oct 3, priced at $229 found 6 days ago

Find the cheapest month to fly from Chicago (ORD) to Aspen (ASE)

September is typically the cheapest month to fly

From $210 - $590 per traveler.

Graph displaying average flight prices per month

Alternative airports near Aspen

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to Eagle County Regional EGE. Average driving time to city center is 1 hour 25 minutes. Flights from $484
EGE
Eagle County Regional
Average driving time to city center1 h 25 min
Flights from $484
Flights from Chicago (ORD) to Aspen (ASE)
Origin airport
O'Hare Intl.
Destination airport
Pitkin County
Airlines serving
American Airlines, Delta, United
Roundtrip price
$191
Distance
1010 mi
Average flight time
2 hours 9 mins

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 September. 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 $110 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 O'Hare Intl. Airport (ORD) to Pitkin County Airport (ASE) cost?
Book cheap return tickets starting at $191 from O'Hare Intl. Airport (ORD) to Pitkin County Airport (ASE). This information is based on the cheapest price found on Expedia for this return journey departing within the next three months. This airfare is for a United flight leaving ORD on August 15 2025 and touching down at ASE. The price was last updated on July 23 2025 and has not changed since.
What is the cheapest month to fly from ORD to ASE?
The cheapest flights from ORD 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 O'Hare Intl. Airport (ORD) to Pitkin County Airport (ASE)?
Hop on a direct flight with United Airlines and head straight from O'Hare Intl. Airport (ORD) to Pitkin County Airport (ASE).
What is the cheapest airline that flies from ORD to ASE?
With tickets starting at $234 for a one-way flight from ORD to ASE, American Airlines is currently the cheapest airline on this route. This fare is based on the lowest price found on Expedia departing within the next three months. The flight takes off from ORD on August 15 2025. Prices were last updated on July 23 2025 and have not changed since.
How many flights per day from O'Hare Intl. Airport (ORD) to Pitkin County Airport (ASE)?
Each day, an average of 4 direct flights take off from O'Hare Intl. Airport (ORD) to Pitkin County Airport (ASE). Select the departure date that best suits your travel plans.
What are the most popular departure times for flights from O'Hare Intl. Airport (ORD) to Pitkin County Airport (ASE)?
Flights between ORD and ASE tend to be busiest at 8 AM. If you want a more relaxed experience and possibly cheaper tickets, look for a time outside the usual busy windows.
What day of the week has the most flights from ORD to ASE?
Travel on a Sunday if you're after the largest selection of flights from O'Hare Intl. Airport (ORD) to Pitkin County Airport (ASE).
What is the earliest flight from O'Hare Intl. Airport (ORD) to Pitkin County Airport (ASE)?
Take the earliest flight at around 8:45AM UTC-6, leaving from O'Hare Intl. Airport (ORD). You'll be in the air for approximately 3h 24m, arriving at Pitkin County Airport (ASE) at approximately 11:09AM UTC-7.
How long does it take to fly from O'Hare Intl. Airport (ORD) to Pitkin County Airport (ASE)?
It takes roughly 3 hours and 21 minutes to cover the 1,000 mi from ORD to ASE.
What is the best time to fly from O'Hare Intl. Airport (ORD) to Pitkin County Airport (ASE)?
To arrive at Pitkin County Airport (ASE) without delays, select a flight that takes off from O'Hare Intl. Airport (ORD) before 3 PM. The chance 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.
What airports do you fly into for Aspen from O'Hare Intl. Airport (ORD)?
Catch a direct flight from O'Hare Intl. Airport (ORD) to Aspen and arrive at Pitkin County Airport (ASE). Another convenient gateway to this destination is Eagle County Regional Airport (EGE).
Is it cheaper to buy a plane ticket from O'Hare Intl. Airport (ORD) to Pitkin County Airport (ASE) last-minute?
Last-minute fares from ORD to ASE are usually more expensive. For the lowest prices, start searching for flights ahead of time. That said, if you can play around with your travel dates, you may score a cheap ticket right before you leave.
Is it cheaper to book an ORD to ASE flight and hotel package?
You'll typically save money by booking an ORD to ASE flight and hotel package compared to booking separately. In fact, you could save hundreds of dollars by bundling with Expedia. And it's simple to manage everything in one convenient place. Once you've chosen your preferred accommodations and flights, consider adding extras such as car rentals, tours and activities.
Can I cancel or change the date of my flight from O'Hare Intl. Airport (ORD) to Pitkin County Airport (ASE)?
You can usually reschedule or cancel your ORD to ASE flight. However, for bookings made more than 24 hours ago, additional fees may apply. Refer to your airline's policies in your itinerary to see what changes are allowed and if any costs are involved. You'll also find more details on our Customer Service portal.

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*Available to One Key members.