S$244 Cheap Flights from Chicago to Aspen

View S$244 flight on Mon, 28 Jul, 2025Opens in a new window

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

  • Plan, book, fly with confidence

  • trending down icon
    Be in the know
    Get alerts if flight prices drop or rise*
  • bex rewards loyalty icon
    Book smarter
    Save up to 40% on select hotels after you book a flight*
  • payments icon
    Earn twice
    Earn your airline miles on top of our rewards
    Sign in

Cheap Flights from Chicago to Aspen (ORD-ASE)

Prices were available within the past 7 days and start at S$244 for one-way flights and S$422 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

United
Wed, 30 Jul - Wed, 6 Aug
ORD
Chicago
ASE
Aspen
S$422 Return, found 15 hours ago
S$422
Return
found 15 hours ago
Select United flight, departing Wed, 30 Jul from Chicago to Aspen, returning Wed, 6 Aug, priced at S$422 found 15 hours ago
United
Fri, 25 Jul - Fri, 1 Aug
ORD
Chicago
ASE
Aspen
S$425 Return, found 5 days ago
S$425
Return
found 5 days ago
Select United flight, departing Fri, 25 Jul from Chicago to Aspen, returning Fri, 1 Aug, priced at S$425 found 5 days ago
United
Wed, 30 Jul - Wed, 6 Aug
ORD
Chicago
ASE
Aspen
S$473 Return, found 15 hours ago
S$473
Return
found 15 hours ago
Select United flight, departing Wed, 30 Jul from Chicago to Aspen, returning Wed, 6 Aug, priced at S$473 found 15 hours ago
United
Wed, 30 Jul - Wed, 6 Aug
ORD
Chicago
ASE
Aspen
S$486 Return, found 15 hours ago
S$486
Return
found 15 hours ago
Select United flight, departing Wed, 30 Jul from Chicago to Aspen, returning Wed, 6 Aug, priced at S$486 found 15 hours ago
United
Mon, 28 Jul - Mon, 4 Aug
ORD
Chicago
ASE
Aspen
S$498 Return, found 1 day ago
S$498
Return
found 1 day ago
Select United flight, departing Mon, 28 Jul from Chicago to Aspen, returning Mon, 4 Aug, priced at S$498 found 1 day ago
American Airlines
Wed, 30 Jul - Wed, 6 Aug
ORD
Chicago
ASE
Aspen
S$506 Return, found 15 hours ago
S$506
Return
found 15 hours ago
Select American Airlines flight, departing Wed, 30 Jul from Chicago to Aspen, returning Wed, 6 Aug, priced at S$506 found 15 hours ago
American Airlines
Wed, 30 Jul - Wed, 6 Aug
ORD
Chicago
ASE
Aspen
S$519 Return, found 15 hours ago
S$519
Return
found 15 hours ago
Select American Airlines flight, departing Wed, 30 Jul from Chicago to Aspen, returning Wed, 6 Aug, priced at S$519 found 15 hours ago
Delta
Wed, 30 Jul - Wed, 6 Aug
ORD
Chicago
ASE
Aspen
S$556 Return, found 15 hours ago
S$556
Return
found 15 hours ago
Select Delta flight, departing Wed, 30 Jul from Chicago to Aspen, returning Wed, 6 Aug, priced at S$556 found 15 hours ago
United
Fri, 25 Jul - Fri, 1 Aug
ORD
Chicago
ASE
Aspen
S$561 Return, found 5 days ago
S$561
Return
found 5 days ago
Select United flight, departing Fri, 25 Jul from Chicago to Aspen, returning Fri, 1 Aug, priced at S$561 found 5 days ago
United
Mon, 28 Jul - Mon, 4 Aug
ORD
Chicago
ASE
Aspen
S$563 Return, found 1 day ago
S$563
Return
found 1 day ago
Select United flight, departing Mon, 28 Jul from Chicago to Aspen, returning Mon, 4 Aug, priced at S$563 found 1 day ago
Chicago to Aspen route information
Origin airport
O'Hare Intl.
Destination airport
Pitkin County
Airlines serving
American Airlines, Delta, United
Return price
S$421
Distance
1616 km
Average flight time
2 hours 11 mins

Perfect flights from Chicago to Aspen

Your Journey from Chicago to Aspen

Start your unforgettable journey with Expedia. Our broad selection of flights from Chicago to Aspen caters to every travel need. Whether you're yearning for a romantic escape, a solo adventure, or a cultural immersion, we've got you covered.
 

Choosing Your Ideal Flight

With Expedia, you have access to a wide range of airlines, including United, Delta, American Airlines. Our selection of flights from O'Hare Intl. to Pitkin County caters to every traveler's requirements, ensuring your journey aligns with your schedule. With options from 20 airlines, you're bound to find the perfect flight.
 

Maximizing Value with Chicago to Aspen Flights

Experience the joy of finding cheap flights from O'Hare Intl. to Pitkin County that fit your budget. Keep an eye out for our special deals and discounts, and check our flexible one-way fares from S$244 and roundtrip prices from S$422*.
 

Pre-Flight Essentials

Ensure a smooth journey from Chicago to Aspen with Expedia. From information about check-in times and in-flight amenities to guidance on baggage policies, we provide all the essentials to prepare you for your flight.
 

Experience the Vibrant Aspen

Picture yourself stepping off the plane in Aspen and immersing yourself in the unique atmosphere of Aspen. From local markets to cultural festivals, each city offers its distinct charm. Make the most of your trip by exploring local attractions and indulging in the local cuisine. With Expedia, explore all this and more, tailored to your budget.
 

Added Convenience on Your Chicago to Aspen Flight

Traveling with Expedia is more than just a flight. We offer details about in-flight amenities, baggage policies, and more to ensure a smooth and hassle-free journey. Choose from our variety of airlines and embark on a memorable journey from Chicago to Aspen.
 

Beyond the Flight – Exploring Aspen

With Expedia, your adventure extends beyond the flight. Explore Aspen at your own pace by renting a car or booking a hotel. Discover hidden gems off the beaten path and create unforgettable memories.
 

Book Your Flight from Chicago to Aspen with Confidence

Planning your next great adventure is a breeze with Expedia. Our user-friendly platform, unbeatable prices, and round-the-clock customer support make your travel experience seamless and stress-free. Embark on your journey from Chicago to Aspen with confidence. Book your travel arrangements with Expedia today.
 
*Note: Prices may vary based on availability and are subject to change.

Frequently asked questions

How much is a flight from ORD to ASE?
Round-trip tickets from O’Hare Airport to ASE start from S$422. This figure is based on fares advertised within the last 7 days on Expedia for flights departing within the next year — make your booking ASAP to avoid missing out. Prices and availability are subject to change. Additional terms apply.
Do I need to pay a cancellation fee if I cancel my flight from O'Hare Intl. Airport (ORD) to Aspen/Pitkin County Airport?
Each air carrier has its own set of terms and conditions. If you decide to cancel your escape, visit our Customer Service Portal.
How do I find cheap flights from O'Hare Airport to ASE that have flexible change policies?
Many airlines offer the option to reschedule your flight without a change fee. All you pay is the difference between the original flight and the new flight. When you’re searching for ORD to Aspen/Pitkin County Airport flights, you’ll see a “no change fees” filter for you to select.
How far is the flight from O'Hare Airport to Aspen/Pitkin County Airport?
It’s around 1,650 kilometres from O’Hare Airport to Pitkin County Airport (ASE), so you’ll be strapped into your seat for a while. Keep yourself occupied by packing things like playing cards (if you’re travelling with friends) or the latest bestseller.
Which airlines fly direct from ORD to Aspen/Pitkin County Airport?
Right now, no airlines offer flights directly from O’Hare Airport to Aspen/Pitkin County Airport. You’ll have to book a flight with one or more stops. To score the best connections and price, lock in your fare well in advance.
Are O'Hare Intl. Airport (ORD) to Pitkin County Airport (ASE) flight tickets cheaper when they're purchased at the last minute?
Last-minute planners can sometimes find a bargain, with some of the cheapest airfares from O’Hare Airport to ASE showing up a few weeks before the date of departure. If you’d rather plan ahead of time, Expedia compares and updates the best flight deals regularly — as early as a year in advance in some cases. It does depend on the carrier though, as not all airlines issue prices that far in advance.

Explore a world of travel with Expedia

Aspen Airports

Vail

Chicago Airports

Chicago

Midway Intl. to Aspen
S$945.90
*Available to Expedia members.