$161 Cheap Flights from Aspen (ASE) to Chicago (ORD)

View $161 flight on Mon, Nov 17, 2025Opens in a new window

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

Cheap Flights from Aspen to Chicago (ASE-ORD)

Prices were available within the past 7 days and start at $161 for one-way flights and $298 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

American Airlines
Mon, Nov 10 - Mon, Nov 17
ASE
Aspen
ORD
Chicago
$298 Roundtrip, found 6 days ago
$298
Roundtrip
found 6 days ago
Select American Airlines flight, departing Mon, Nov 10 from Aspen to Chicago, returning Mon, Nov 17, priced at $298 found 6 days ago
United
Sat, May 30 - Wed, Jun 3
ASE
Aspen
ORD
Chicago
$309 Roundtrip, found 5 days ago
$309
Roundtrip
found 5 days ago
Select United flight, departing Sat, May 30 from Aspen to Chicago, returning Wed, Jun 3, priced at $309 found 5 days ago
United
Thu, Dec 18 - Sun, Dec 21
ASE
Aspen
ORD
Chicago
$311 Roundtrip, found 3 days ago
$311
Roundtrip
found 3 days ago
Select United flight, departing Thu, Dec 18 from Aspen to Chicago, returning Sun, Dec 21, priced at $311 found 3 days ago
Delta
Mon, Nov 10 - Mon, Nov 17
ASE
Aspen
ORD
Chicago
$316 Roundtrip, found 6 days ago
$316
Roundtrip
found 6 days ago
Select Delta flight, departing Mon, Nov 10 from Aspen to Chicago, returning Mon, Nov 17, priced at $316 found 6 days ago
Delta
Sat, Nov 15 - Sun, Nov 16
ASE
Aspen
ORD
Chicago
$318 Roundtrip, found 8 hours ago
$318
Roundtrip
found 8 hours ago
Select Delta flight, departing Sat, Nov 15 from Aspen to Chicago, returning Sun, Nov 16, priced at $318 found 8 hours ago
American Airlines
Tue, Jan 27 - Sat, Jan 31
ASE
Aspen
ORD
Chicago
$320 Roundtrip, found 4 days ago
$320
Roundtrip
found 4 days ago
Select American Airlines flight, departing Tue, Jan 27 from Aspen to Chicago, returning Sat, Jan 31, priced at $320 found 4 days ago
United
Thu, Dec 18 - Sun, Dec 21
ASE
Aspen
ORD
Chicago
$321 Roundtrip, found 3 days ago
$321
Roundtrip
found 3 days ago
Select United flight, departing Thu, Dec 18 from Aspen to Chicago, returning Sun, Dec 21, priced at $321 found 3 days ago
United
Mon, Nov 10 - Mon, Nov 17
ASE
Aspen
ORD
Chicago
$324 Roundtrip, found 6 days ago
$324
Roundtrip
found 6 days ago
Select United flight, departing Mon, Nov 10 from Aspen to Chicago, returning Mon, Nov 17, priced at $324 found 6 days ago
United
Fri, Feb 13 - Fri, Feb 20
ASE
Aspen
ORD
Chicago
$329 Roundtrip, found 4 days ago
$329
Roundtrip
found 4 days ago
Select United flight, departing Fri, Feb 13 from Aspen to Chicago, returning Fri, Feb 20, priced at $329 found 4 days ago
United
Mon, Dec 29 - Tue, Jan 6
ASE
Aspen
ORD
Chicago
$330 Roundtrip, found 6 hours ago
$330
Roundtrip
found 6 hours ago
Select United flight, departing Mon, Dec 29 from Aspen to Chicago, returning Tue, Jan 6, priced at $330 found 6 hours ago

Alternative airports near Chicago

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

Select flight to Midway Intl. MDW. Closest option available. Average driving time to city center is 16 minutes. Flights from $1,249
MDW
Midway Intl.
Closest
Average driving time to city center16 min
Flights from $1,249

Frequently asked questions

How much does a flight from Pitkin County Airport (ASE) to O'Hare Intl. Airport (ORD) cost?
Get a cheap one-way flight from $161 or cheap return flight from $298 from Pitkin County Airport (ASE) to O'Hare Intl. Airport (ORD) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to see our cheapest flight offers on this route.
What is the cheapest month to fly from Pitkin County Airport (ASE) to O'Hare Intl. Airport (ORD)?
November is the least expensive month to fly from ASE to ORD. Planning your trip for the off-season is often the key to finding better deals on flights.
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 Pitkin County Airport (ASE) to O'Hare Intl. Airport (ORD)?
The cheapest airline to offer flights between Pitkin County Airport (ASE) and O'Hare Intl. Airport (ORD) will vary based on your travel plans. American Airlines and United Airlines are just some good options offering well-priced fares. Use Expedia's search tool to compare airlines in one place and find the right ASE to ORD flight that fits your budget.
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.

Travel information

Origin airport
Pitkin County
Destination airport
O'Hare Intl.
Airlines serving
American Airlines, Delta, United
Roundtrip price
$298
Distance
1010 mi

Book with confidence

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 November. 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 $161 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.

 

Aspen to Chicago Flights

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*Available to One Key members.