$145 Cheap Flights from Aspen (ASE) to Chicago (ORD)

View $145 flight on Thu, Jun 19, 2025Opens in a new window

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

Find available prices by choosing your travel dates.

Cheap Flights from Aspen to Chicago (ASE-ORD)

Prices were available within the past 7 days and start at $145 for one-way flights and $239 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

American Airlines
Fri, Jun 6 - Sun, Jun 8
ASE
Aspen
ORD
Chicago
$239 Roundtrip, found 1 hour ago
$239
Roundtrip
found 1 hour ago
Select American Airlines flight, departing Fri, Jun 6 from Aspen to Chicago, returning Sun, Jun 8, priced at $239 found 1 hour ago
United
Fri, Jun 6 - Sun, Jun 8
ASE
Aspen
ORD
Chicago
$249 Roundtrip, found 1 hour ago
$249
Roundtrip
found 1 hour ago
Select United flight, departing Fri, Jun 6 from Aspen to Chicago, returning Sun, Jun 8, priced at $249 found 1 hour ago
United
Fri, Jun 6 - Sun, Jun 8
ASE
Aspen
ORD
Chicago
$256 Roundtrip, found 1 hour ago
$256
Roundtrip
found 1 hour ago
Select United flight, departing Fri, Jun 6 from Aspen to Chicago, returning Sun, Jun 8, priced at $256 found 1 hour ago
Delta
Tue, Jun 3 - Sun, Jun 15
ASE
Aspen
ORD
Chicago
$259 Roundtrip, found 1 hour ago
$259
Roundtrip
found 1 hour ago
Select Delta flight, departing Tue, Jun 3 from Aspen to Chicago, returning Sun, Jun 15, priced at $259 found 1 hour ago
American Airlines
Fri, Jun 27 - Sat, Jul 5
ASE
Aspen
ORD
Chicago
$264 Roundtrip, found 5 hours ago
$264
Roundtrip
found 5 hours ago
Select American Airlines flight, departing Fri, Jun 27 from Aspen to Chicago, returning Sat, Jul 5, priced at $264 found 5 hours ago
United
Fri, Jun 6 - Sun, Jun 8
ASE
Aspen
ORD
Chicago
$265 Roundtrip, found 1 hour ago
$265
Roundtrip
found 1 hour ago
Select United flight, departing Fri, Jun 6 from Aspen to Chicago, returning Sun, Jun 8, priced at $265 found 1 hour ago
United
Thu, Aug 28 - Sun, Aug 31
ASE
Aspen
ORD
Chicago
$272 Roundtrip, found 1 day ago
$272
Roundtrip
found 1 day ago
Select United flight, departing Thu, Aug 28 from Aspen to Chicago, returning Sun, Aug 31, priced at $272 found 1 day ago
American Airlines
Tue, Aug 5 - Sun, Aug 10
ASE
Aspen
ORD
Chicago
$274 Roundtrip, found 1 hour ago
$274
Roundtrip
found 1 hour ago
Select American Airlines flight, departing Tue, Aug 5 from Aspen to Chicago, returning Sun, Aug 10, priced at $274 found 1 hour ago
United
Fri, Jun 6 - Sun, Jun 8
ASE
Aspen
ORD
Chicago
$276 Roundtrip, found 1 hour ago
$276
Roundtrip
found 1 hour ago
Select United flight, departing Fri, Jun 6 from Aspen to Chicago, returning Sun, Jun 8, priced at $276 found 1 hour ago
United
Thu, Jun 12 - Sun, Jun 15
ASE
Aspen
ORD
Chicago
$278 Roundtrip, found 3 days ago
$278
Roundtrip
found 3 days ago
Select United flight, departing Thu, Jun 12 from Aspen to Chicago, returning Sun, Jun 15, priced at $278 found 3 days ago
Flights from Aspen (ASE) to Chicago (ORD)
Origin airport
Pitkin County
Destination airport
O'Hare Intl.
Airlines serving
American Airlines, Delta, United
Roundtrip price
$239
Distance
1010 mi

Aspen to Chicago Flights

The cheapest times to fly from Aspen to Chicago

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 Aspen to Chicago are during the month of June. You can find some of the cheapest flights from Aspen to Chicago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Aspen to Chicago

Sunday is one of the best days to book for cheap flights from Aspen to Chicago: 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 Aspen to Chicago

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 Aspen to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from $145 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 Aspen to Chicago 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 Aspen to Chicago 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 Pitkin County Airport (ASE) to O'Hare Intl. Airport (ORD) cost?
You can find cheap return fares from Pitkin County Airport (ASE) to O’Hare Intl. Airport (ORD) starting at $300. Book your seat and get ready for takeoff. 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 ASE on April 25 2025 and touching down at ORD. The price was last updated on April 24 2025 and has not changed since.
What is the cheapest month to fly from ASE to ORD?
The cheapest flights from ASE to ORD 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 Pitkin County Airport (ASE) to O'Hare Intl. Airport (ORD)?
Jump on a nonstop flight with United Airlines and travel straight from Pitkin County Airport (ASE) to O’Hare Intl. Airport (ORD).
What is the cheapest airline that flies from ASE to ORD?
Right now, the cheapest carrier offering one-way flights from ASE to ORD is United. You can book a seat on this route from $145. This fare is based on the lowest price found on Expedia departing within the next three months. The flight takes off from ASE on June 10 2025. Prices were last updated on April 24 2025 and have not changed since.
How many flights per day from Pitkin County Airport (ASE) to O'Hare Intl. Airport (ORD)?
Every day, an average of 4 direct flights take off from Pitkin County Airport (ASE) to O’Hare Intl. Airport (ORD). Choose the departure that fits your schedule best.
What are the most popular departure times for flights from Pitkin County Airport (ASE) to O'Hare Intl. Airport (ORD)?
The 12 PM departures from ASE to ORD are the top choice for many travelers. They can also be more expensive. If you’re looking to save, book during off-peak hours.
What day of the week has the most flights from ASE to ORD?
Travel on a Friday if you’re after the largest selection of flights from Pitkin County Airport (ASE) to O’Hare Intl. Airport (ORD).
What is the earliest flight from Pitkin County Airport (ASE) to O'Hare Intl. Airport (ORD)?
Pitkin County Airport (ASE)’s earliest flight to O’Hare Intl. Airport (ORD) takes off at approximately 8:15AM UTC-7. With a total journey time of 3h 8m, you’ll arrive at around 12:23PM UTC-6.
How long does it take to fly from Pitkin County Airport (ASE) to O'Hare Intl. Airport (ORD)?
It takes roughly 3 hours and 1 minute to travel the 1,000 mi from ASE to ORD.
What is the best time to fly from Pitkin County Airport (ASE) to O'Hare Intl. Airport (ORD)?
To avoid possible delays on the Pitkin County Airport (ASE) to O’Hare Intl. Airport (ORD) route, travel before 3 PM. Flights after this time are 22% more likely to be 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.
What airports do you fly into for Chicago from Pitkin County Airport (ASE)?
O’Hare Intl. Airport (ORD) is the only airport in Chicago with direct flights from Pitkin County Airport (ASE). Check out the available options and find affordable fares on Expedia.
Is it cheaper to buy a plane ticket from Pitkin County Airport (ASE) to O'Hare Intl. Airport (ORD) last-minute?
Last-minute fares from ASE to ORD are usually more expensive. To lock in the lowest rates, start looking for flights as soon as possible. That being said, if you’re flexible with your travel plans, you may score a cheap fare right before your trip.
Is it cheaper to book an ASE to ORD flight and hotel package?
Compared with arranging flights and hotels separately, booking an ASE to ORD flight and hotel package with Expedia could lead to significant savings. What’s more, having everything in one convenient place will take the stress out of planning your trip. Just secure your flights and select from our wide range of stays, then personalize your trip with other add-ons like tours, car rentals and activities.
Can I cancel or change the date of my flight from Pitkin County Airport (ASE) to O'Hare Intl. Airport (ORD)?
It’s generally possible to cancel or reschedule your ASE to ORD flight. However, if it’s been more than 24 hours since booking, additional fees may apply. Refer to your airline’s policies in your itinerary to see what changes are allowed and whether any costs are involved. You’ll also find more details on our Customer Service portal.

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*Available to One Key members.