CHI - ASE

$141 Find Cheap Flights from Chicago to Aspen

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Aspen departing on 10/12. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy

KAYAK searches hundreds of travel sites at once for deals on flights to Aspen

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Aspen, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Aspen, as well as popular online travel agencies
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Flights Deals

Cheap Flights from Chicago to Aspen (CHI-ASE)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to Aspen that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Chicago to Aspen

Tue, Jul 22 - Tue, Jul 29
United Airlines Logo
5:00 am - 8:42 amORD-ASE
4h 42m1 stop
United Airlines Logo
6:15 pm - 12:30 amASE-ORD
5h 15m1 stop
$249United Airlines
Find Deal
Sun, Jul 13 - Tue, Jul 15
United Airlines Logo
5:00 am - 8:42 amORD-ASE
4h 42m1 stop
United Airlines Logo
11:36 am - 6:24 pmASE-ORD
5h 48m1 stop
$252United Airlines
Find Deal
Thu, Jun 26 - Tue, Jul 8
United Airlines Logo
5:00 am - 8:42 amORD-ASE
4h 42m1 stop
United Airlines Logo
6:15 pm - 12:30 amASE-ORD
5h 15m1 stop
$264United Airlines
Find Deal
Fri, Jun 27 - Tue, Jul 1
United Airlines Logo
5:00 am - 8:42 amORD-ASE
4h 42m1 stop
United Airlines Logo
7:50 am - 3:05 pmASE-ORD
6h 15m1 stop
$265United Airlines
Find Deal
Mon, Aug 18 - Wed, Aug 20
American Airlines Logo
9:40 am - 11:46 amORD-ASE
3h 06mnonstop
American Airlines Logo
12:03 pm - 4:01 pmASE-ORD
2h 58mnonstop
$317American Airlines
Find Deal
Tue, Jul 22 - Tue, Jul 29
American Airlines Logo
5:00 am - 9:50 amORD-ASE
5h 50m1 stop
American Airlines Logo
12:06 pm - 4:04 pmASE-ORD
2h 58mnonstop
$327American Airlines
Find Deal
Mon, Aug 18 - Wed, Aug 20
American Airlines Logo
6:00 am - 11:31 amORD-ASE
6h 31m1 stop
American Airlines Logo
12:16 pm - 7:17 pmASE-ORD
6h 01m1 stop
$336American Airlines
Find Deal
Sun, Jul 6 - Thu, Jul 10
Delta Logo
5:35 am - 11:22 amORD-ASE
6h 47m1 stop
Delta Logo
8:05 am - 8:24 pmASE-ORD
11h 19m2 stops
$604Delta
Find Deal
Thu, Aug 28 - Sat, Aug 30
Delta Logo
6:00 am - 11:21 amMDW-ASE
6h 21m1 stop
Delta Logo
7:16 am - 3:28 pmASE-MDW
7h 12m1 stop
$709Delta
Find Deal
Tue, Jul 22 - Tue, Jul 29
Delta Logo
5:35 am - 11:21 amORD-ASE
6h 46m1 stop
Delta Logo
8:05 am - 8:15 pmASE-ORD
11h 10m2 stops
$764Delta
Find Deal
Expert advice

Expert advice for your flight from Chicago to Aspen

 
Snippets provided in this section are AI-generated based on a summarization of KAYAK-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Airlines
United Airlines

United's Premier Access offers priority check-in and boarding for a smoother travel experience.


United's Economy Plus offers up to six inches more legroom for added comfort.

American Airlines

American's Main Cabin Extra includes early boarding and complimentary drinks for a small fee.


American's Admirals Clubs offer snacks, drinks, and travel assistance for a relaxing pre-flight experience.

Our travel experts
Stefanie Waldek

Stefanie Waldek

Expert on United Airlines

Stefanie Waldek

Stefanie Waldek

Stefanie Waldek is a freelance space, travel, and design writer based in Saratoga Springs, NY. Her words have appeared in Space.com, Travel + Leisure, Condé Nast Traveler, Architectural Digest, and House Beautiful, among other publications. An expert in aviation and expedition cruising, Stefanie is frequently up in the air or on the sea, likely en route to Antarctica or the Arctic.

Read more
Harriet Baskas

Harriet Baskas

Expert on American Airlines

Harriet Baskas

Harriet Baskas

Harriet is an award-winning journalist who is happiest in an airport or an unusual museum. Her stories about airports, air travel, and the business of travel have appeared on NBC News, CNBC, USA TODAY, The Points Guy and other outlets. She is the creator of the StuckatTheAirport.com blog and the author of nine books. When not out on the road or exploring the latest airport amenities, she’s home in Seattle getting ready for the next adventure.

Read more
Useful Info

KAYAK's insights & trends for Chicago to Aspen flights

Get data-powered insights and trends into flights from Chicago to Aspen to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest Chicago to Aspen flight route?

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for round-trip flights from Chicago to Aspen.

Our data shows that the cheapest route for a return flight from Chicago to Aspen cost $232 and was between Chicago O'Hare Intl Airport (ORD) and Aspen (ASE). On average, the best prices are found if you fly this route. The average price for a return flight for this route is $232.

What’s the cheapest day of the week to fly from Chicago to Aspen?

The average price of all round-trip flights from Chicago to Aspen clicked on KAYAK for each day over the last 12 months.

Your flight ticket price will generally be cheaper if you fly to Aspen on a Tuesday and more expensive on a Thursday. On your return trip to Chicago, you should consider flying back on a Thursday, and avoid Sundays for better deals.

What is the cheapest month to fly from Chicago to Aspen?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago to Aspen, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Chicago to Aspen is January, where tickets cost $449 (return) on average. On the other hand, the most expensive months are November and April, where the average cost of round-trip tickets is $871 and $617 respectively.

Can I save money by flying with a layover from Chicago to Aspen?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 1 stop layover the cheapest option at $748 on average.

How far in advance should I book a flight from Chicago to Aspen?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Chicago to Aspen, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Chicago to Aspen, you should book around 2 weeks before departure. For the absolute cheapest price, our data suggests you should book 20 weeks before departure.

Good to know

Low seasonMay
High seasonDecember
Cheapest flight$141
Best time to beat the crowds with an average 14% drop in price.
Most popular time to fly with an average 1% increase in price.
Flight from Chicago O'Hare Airport to Aspen

When to book flights from Chicago to Aspen

Are your dates flexible? Find out the best times to travel from Chicago to Aspen based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking flights from Chicago to Aspen

  • What is the cheapest flight from Chicago to Aspen?

    In the last 3 days, the lowest price for a flight from Chicago to Aspen was $141 for a one-way ticket and $249 for a round-trip.

  • Do I need a passport to fly between Chicago and Aspen?

    A passport is not required to fly from Chicago to Aspen.

  • Which airports will I be using when flying from Chicago to Aspen?

    Chicago has 2 major airports: Chicago Midway and Chicago O'Hare Intl. Aspen Pitkin County is the only airport in Aspen. You’ll usually find the cheapest deals if you fly from Chicago O'Hare Airport.

  • Which airlines offer Wi-Fi service onboard planes from Chicago to Aspen?

    Only American Airlines offers inflight Wi-Fi service on the Chicago to Aspen flight route.

  • Which aircraft models fly most regularly from Chicago to Aspen?

    The Canadair (Bombardier) Regional Jet 700 is the aircraft model that flies most regularly on the Chicago to Aspen flight route.

  • Which airline alliances offer flights from Chicago to Aspen?

    oneworld, and Star Alliance are the airline alliances operating flights between Chicago and Aspen, with Star Alliance being the most commonly used for this route.

  • On which days can I fly direct from Chicago to Aspen?

    There are nonstop flights from Chicago to Aspen on a daily basis.

  • Which is the best airline for flights from Chicago to Aspen, United Airlines or American Airlines?

    The two airlines most popular with KAYAK users for flights from Chicago to Aspen are United Airlines and American Airlines. With an average price for the route of $530 and an overall rating of 7.4, United Airlines is the most popular choice. American Airlines is also a great choice for the route, with an average price of $516 and an overall rating of 7.2.

  • How does KAYAK find such low prices on flights from Chicago to Aspen?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago to Aspen.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago to Aspen?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Aspen from Chicago is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago to Aspen?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Aspen with an airline and back to Chicago with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago to Aspen?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Aspen from Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

KAYAK’s top tips for finding a cheap flight from Chicago to Aspen

  • Looking for a cheap flight? 25% of our users found flights on this route for $195 or less one-way and $420 or less round-trip.

Prefer to fly direct from Chicago to Aspen?

Find which airlines fly direct from Chicago to Aspen Pitkin County Airport, which days they fly and book direct flights.

Direct departures

Chicago to Aspen Pitkin County

Monday

American Airlines, United Airlines

American Airlines, United Airlines

Tuesday

American Airlines, United Airlines

American Airlines, United Airlines

Wednesday

American Airlines, United Airlines

American Airlines, United Airlines

Thursday

American Airlines, United Airlines

American Airlines, United Airlines

Friday

American Airlines, United Airlines

American Airlines, United Airlines

Saturday

American Airlines, United Airlines

American Airlines, United Airlines

Sunday

American Airlines, United Airlines

American Airlines, United Airlines

See more direct flights

Direct returns

Aspen Pitkin County to Chicago

Monday

American Airlines, United Airlines

American Airlines, United Airlines

Tuesday

American Airlines, United Airlines

American Airlines, United Airlines

Wednesday

American Airlines, United Airlines

American Airlines, United Airlines

Thursday

American Airlines, United Airlines

American Airlines, United Airlines

Friday

American Airlines, United Airlines

American Airlines, United Airlines

Saturday

American Airlines, United Airlines

American Airlines, United Airlines

Sunday

American Airlines, United Airlines

American Airlines, United Airlines

See more direct flights
See more direct flights

Top airlines flying from Chicago to Aspen

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Aspen. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Chicago to Aspen? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.4
United AirlinesOverall score based on 8790 reviews
7.0Entertainment
7.7Boarding
7.3Comfort
6.6Food
8.1Crew
Airline reviews

I was charged for my daughters bag when I am supposed to receive two free checked bags with my United Explorer card.

6.0 GoodAndrea, May 2025ORD - ATL
Read more United Airlines reviews

I was charged for my daughters bag when I am supposed to receive two free checked bags with my United Explorer card.

The schedule to Moline changed 5 times. The gate changed 6 times. That is a pathetic way to run an airline. No wonder that no one in our company flies on United Express to or from Moline. Changes happen most of the time. I learned my lesson on this trip…never again!

Flight was great. Efficient boarding. Short flight. Early arrival. Friendly flight crew. The entertainment system did not work well. Could not access it until the aircraft reached 10K feet or more. Lots of glitches.

A bit rush for transit. Food and entertainment are not available

Smooth boarding process. Early departure, smooth flight, early arrival. The entertainment package has very good recent movie options. The flight crew were friendly and professional.

My flight was scheduled for about 6:05 departure. There were 11 gate changes from 4-7pm and the flight was 3 hours delayed due to operational issues. The plane taxied around the airport for about half an hour before stopping to be de-iced. It would have been nice if we were alerted of the plan to de-ice prior to the 30 minute drive around the airport. The flight attendant was friendly, which was the only redeeming thing about this flight. As a former flight attendant for United, I was extremely disappointed.

Delays took 2hours and thirty minutes making me miss my connecting flight and make me sit in the Chicago airport for 9 hours

Had a short delay once we boarded the aircraft in Chicago, but it was fixed in no time flat then we were on our way. The pilot was able to make up the time lost and we landed 5 minute later then schedualed . Great service

Our seats were all the way in back of the plane,

The seats on this flight were almost roomy enough to be the basic amount needed for human existence. I think my favorite part of this flight was it landed at an A gate, which was the most palatial part of Sea-Tac I've ever seen - a massive improvement from the S gates.

I have long legs, my foot was out in the aisle and when a flight attendant came walking by and I didn't notice, instead of saying "excuse me" or anything like that, she kicked my foot. Extremely rude

Excellent! The gate agents were kind enough to rebook me on an earlier flight saving me from a 6 hour layover. Even my luggage made it despite the fact that the connection was technically too narrow. The flight itself was very comfortable, roomy, and clean. Plenty of space for my carryon items with plugs to charge my phone. After a long international flight of 14 hours, this was an excellent way to end my travels!

Great experience. Flight boarded easily. Departed early. Smooth flight. Great arrival in DC--almost no taxing! Almost direct to gate from runway. Crew was terrific. Same cookies and beverages in main cabin. I did not use the entertainment system on this flight.

Most of the delay was due to weather which is not what was at issue here. One delay was due to a missing flashlight and in the end the flashlight was actually found on the plane. The entertainment system is very limited. Live TV options offer only a few channels that are not very appealing. Boarding and deplaning are always difficult. It just takes too much time to get on and off the plane. On the plus side, I missed my connecting flight, but was easily able to book a later flight from the app while enroute.

You were more on time than United. I'm so over united delays.

The meals were mediocre and the alcohol selection was poor. I enjoyed the selection of movies and other entertainment.

I chatted with the captain before the flight, and similarly during the welcome announcement, he warned of a turbulent flight that may impact the in-flight service. However, once at altitude, he announced that the weather changed and he immediately turned off the seatbelt sign. But it appeared the cabin crew had already decided to take off this flight. They remained seated and then just chatted in the galley. The flight was fully catered, but only first class received service.

My flight attendant was attentive! The elderly person next to me was flatulent and the flight attendant could see that I was in distress and brought me some face masks

My boarding pass wouldn't pull up in the app very easily and had to really dig through my email. That caused a delay in TSA..

I had a TERRIBLE experience with the AA crew. I believe it was disability-related. It’s unlikely I will fly AA again.

Everything you need to know for your flight from Chicago to Aspen

Information on your arrival and departure airports

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