ASE - CHI

$172 Find Cheap Flights from Aspen to Chicago

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Aspen to Chicago departing on 5/28. 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, 0 bags

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

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Aspen to Chicago, 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 Aspen to Chicago, as well as popular online travel agencies
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41,299,237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$343
American Airlines
Thu 7/9Mon 7/13
ASE - ORD • Non-stop
Cheapest one-way
$172
United Airlines
Thu 5/28
ASE - ORD • Non-stop
Advice from real travelers
AI-powered summary based on content written by travel experts. AI can make mistakes.
United's Economy Plus offers extra legroom on this route.
American Airlines provides early boarding with Main Cabin Extra.
Expert advice
Expert advice
Expert advice
Expert advice
Top airlines
Cheapest • from $343 (round-trip)
Best reviews • 7.4 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
You can fly direct with United Airlines and American Airlines. Average duration is 3h 05m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Top routes
Cheapest
Most popular
Insights
Insights
Insights
Insights
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We hope you love your trip to Chicago!
Flight Deals
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Expert advice
Flight Deals

Cheap Flights from Aspen to Chicago (ASE-CHI)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Aspen to Chicago 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 Aspen to Chicago

Thu, Jul 9 - Mon, Jul 13
American Airlines Logo
7:00 am - 11:07 am
ASE
-
ORD
3h 07mnonstop
American Airlines Logo
7:49 pm - 9:58 pm
ORD
-
ASE
3h 09mnonstop
$343American Airlines
Thu, Jul 9 - Tue, Jul 14
United Airlines Logo
5:10 pm - 12:44 am
ASE
-
ORD
6h 34m
1 stop
United Airlines Logo
7:45 pm - 10:00 pm
ORD
-
ASE
3h 15mnonstop
$353United Airlines
Mon, Jul 27 - Mon, Aug 3
American Airlines Logo
7:00 am - 11:07 am
ASE
-
ORD
3h 07mnonstop
American Airlines Logo
7:49 pm - 9:58 pm
ORD
-
ASE
3h 09mnonstop
$356American Airlines
Thu, Jul 9 - Tue, Jul 14
United Airlines Logo
5:10 pm - 11:19 pm
ASE
-
ORD
5h 09m
1 stop
United Airlines Logo
5:00 am - 8:46 am
ORD
-
ASE
4h 46m
1 stop
$363United Airlines
Sat, Jun 6 - Tue, Jun 9
United Airlines Logo
1:22 pm - 8:30 pm
ASE
-
ORD
6h 08m
1 stop
United Airlines Logo
7:45 pm - 10:00 pm
ORD
-
ASE
3h 15mnonstop
$366United Airlines
Thu, Jul 9 - Tue, Jul 14
Delta Logo
7:30 am - 8:31 pm
ASE
-
ORD
12h 01m
2 stops
Delta Logo
5:15 am - 11:23 am
ORD
-
ASE
7h 08m
1 stop
$368Delta
Sat, Jun 6 - Tue, Jun 9
United Airlines Logo
2:22 pm - 8:30 pm
ASE
-
ORD
5h 08m
1 stop
United Airlines Logo
5:00 am - 8:46 am
ORD
-
ASE
4h 46m
1 stop
$376United Airlines
Fri, Jun 19 - Tue, Jul 7
American Airlines Logo
11:26 am - 3:35 pm
ASE
-
ORD
3h 09mnonstop
American Airlines Logo
11:09 am - 1:17 pm
ORD
-
ASE
3h 08mnonstop
$381American Airlines
Fri, May 22 - Sun, May 24
Delta Logo
8:05 am - 6:35 pm
ASE
-
ORD
9h 30m
1 stop
Delta Logo
5:30 am - 11:19 am
ORD
-
ASE
6h 49m
1 stop
$391Delta
Thu, Jul 9 - Tue, Jul 14
Delta Logo
7:30 am - 4:15 pm
ASE
-
MDW
7h 45m
1 stop
Delta Logo
6:05 am - 11:23 am
MDW
-
ASE
6h 18m
1 stop
$461Delta
Booking Insights

KAYAK's insights & trends for Aspen to Chicago flights

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

What is the cheapest Aspen to Chicago flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest return flight from Aspen to Chicago costs $408 on the route between Aspen (ASE) and Chicago O'Hare Intl Airport (ORD). It is also the most popular route.

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

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

When flying from Aspen to Chicago, you should consider leaving on a Wednesday and avoid Mondays if you are looking for the best rates. For your return to Aspen, you’ll find the best rates on Tuesdays and the most expensive ones on Thursdays.

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

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.

No, with an average price for the route of $429, prices are generally cheapest when you fly direct.

Expert advice

Expert advice for your flight from Aspen to Chicago

 
AI-powered summary based on content written by travel experts. AI can make mistakes.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Our travel experts
Stefanie Waldek

Stefanie Waldek

Expert on United Airlines

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.

Harriet Baskas

Harriet Baskas

Expert on American Airlines

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.

Good to know

Cheapest flight$172
Flight from Aspen to Chicago O'Hare Airport

When to book flights from Aspen to Chicago

Are your dates flexible? Find out the best times to travel from Aspen to Chicago 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 Aspen to Chicago

  • How many flights are there between Aspen and Chicago per day?

    Each day, there are 2 nonstop flights that take off from Aspen and land in Chicago, with an average flight time of 3h 05m. The most common departure time is 9:00 am and most flights take off in the morning. Each week, there are 14 flights and there are the same amount of flights each day (2).

  • What is the cheapest flight from Aspen to Chicago?

    In the last 3 days, the lowest price for a flight from Aspen to Chicago was $172 for a one-way ticket and $343 for a round-trip.

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

    Even though you are not required to have a passport, keep in mind that an official ID is needed to board the airplane.

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

    On your way to Chicago, you’ll fly out from Aspen Pitkin County. You’ll be landing in one of Chicago’s 2 airports: Chicago Midway or Chicago O'Hare Intl.

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

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

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

    The Embraer 175 (Enhanced Winglets) is the aircraft model that flies most regularly on the Aspen to Chicago flight route.

  • Which airline alliances offer flights from Aspen to Chicago?

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

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

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

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

    The two airlines most popular with KAYAK users for flights from Aspen to Chicago are United Airlines and American Airlines. With an average price for the route of $376 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 $340 and an overall rating of 7.1.

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

    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 Aspen to Chicago.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Aspen 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 Aspen to Chicago?

    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 Chicago with an airline and back to Aspen with another airline.

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

    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 Chicago from Aspen 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 Aspen to Chicago

  • Looking for a cheap flight? 25% of our users found flights on this route for $336 or less one-way and $440 or less round-trip.

Prefer to fly direct from Aspen to Chicago?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Aspen Pitkin County to Chicago.
Find which airlines fly direct from Aspen Pitkin County Airport to Chicago, which days they fly and book direct flights.

Direct departures

Aspen Pitkin County to Chicago

Monday

United Airlines,American Airlines

United Airlines,American Airlines

Tuesday

United Airlines,American Airlines

United Airlines,American Airlines

Wednesday

United Airlines,American Airlines

United Airlines,American Airlines

Thursday

United Airlines,American Airlines

United Airlines,American Airlines

Friday

United Airlines,American Airlines

United Airlines,American Airlines

Saturday

United Airlines,American Airlines

United Airlines,American Airlines

Sunday

United Airlines,American Airlines

United Airlines,American Airlines

See more direct flights

Direct returns

Chicago to Aspen Pitkin County

Monday

United Airlines,American Airlines

United Airlines,American Airlines

Tuesday

United Airlines,American Airlines

United Airlines,American Airlines

Wednesday

United Airlines,American Airlines

United Airlines,American Airlines

Thursday

United Airlines,American Airlines

United Airlines,American Airlines

Friday

United Airlines,American Airlines

United Airlines,American Airlines

Saturday

United Airlines,American Airlines

United Airlines,American Airlines

Sunday

United Airlines,American Airlines

United Airlines,American Airlines

See more direct flights

Reviews of the top airlines flying from Aspen to Chicago

 
See real verified KAYAK customer reviews for airlines flying from Aspen to Chicago. 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 Aspen to Chicago? 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 9613 reviews
7.1Entertainment
6.6Food
8.1Crew
7.3Comfort
7.7Boarding
Airline reviews

boarded early to only find out that flight would sit at gate for 45 min to an hour. Landed in chicago and sat on runway for over an hour before got to gate. Total delay was extensive for a 45 min flight door to door.

2.0 MediocreKelly, Apr 2026
MLI - ORD
Read more United Airlines reviews

boarded early to only find out that flight would sit at gate for 45 min to an hour. Landed in chicago and sat on runway for over an hour before got to gate. Total delay was extensive for a 45 min flight door to door.

The flight was significantly delayed. The inbound flight from EWR was delayed departing because of mechanical problems. My original departure from CLT was 5:28 pm but due to the delay of the inbound flight, after arrival, deplaning, cleaning, boarding, we did not push back from the gate until 9:00 pm. Once in the air, the flight was smooth and what was originally supposed to be an arrival in ORD at 7:30 pm local time turned out to be 9:35 pm.

The flight I was supposed to be on was supposed to take off at 1:50 from State College. It was delayed over and over and over again until somehow I had to rebook on a flight that was supposed to have left State College at 8 am that morning but didn't end up taking off until almost 6 pm. Not only was this completely unacceptable, the "token from United" was a 15 dollar meal voucher that has to be used by today. I would personally like some miles added to my account for this inconvenience. I was in transit for 8 hours from the time I arrive at State College Aiport to when I got home. I was supposed to be home at 3 pm and I returned at 8 pm. Unacceptable. I have not been on an on Time united flight in nearly 5 years.

newer aircraft, ability to connect my headset via blue tooth for entertainment.

Very comfortable flight, snacks and drinks were good, good communication from crew. Could have used a little more information on timing of boarding for group 5

Great flight. Got to watch a movie. Smooth flight and early arrival at ORD.

It was better than excellent. The staff in Mason City were great. The young woman that pushed my wheelchair did more than could be expected of her. She came from India 17 years ago. I don't remember her name.

After arriving in Chicago, we were taxiing for 1.5 hours with infrequent and untruthful updates about the amount of time it would take to arrive at the gate. Minimally, the team could have provided timing expectations that were more truthful, especially one their original expectations were not met.

Every staff member was professional, friendly and courteous. The pizza twist was ok. It was warm but too much dough.

I had a terrible experience. My flight got delayed from Atlanta to Chicago on Monday April 6, 2026, and that led to me missing my next flight to Brussels. United Airlines didn’t provide me with any accommodation for shelter. I had to sleep at the airport in Chicago. The next flight I was put on didn’t leave until the evening hours of Tuesday 4/7/2026.

It was good, the staff was great, and the food, was as usual, tea and biscuit. Bathroom was clean, and the plane was clean as well.

Very good I can’t complain one bit. Thank you American Airlines for making my flight enjoyable and safe!

The staff and service on American Airlines were truly outstanding. I had requested wheelchair assistance for my mother due to her knee issues, and the team went above and beyond every step of the way—from boarding in Boston to our arrival in Chicago. Their care, professionalism, and attentiveness made the entire experience smooth and stress-free. I’m very grateful for the support they provided.

American flight was diverted and delayed but app didn’t show that information so I wasn’t able to change my connection until the last min.

The new planes (American Eagle) are beautiful and especially comfortable. The flight attendants are consistently professional and courteous. And, while it may seem inconsequential, the new liquid tube of coffee creamer—in contrast to the powdered coffee creamer—makes all the difference in a cup of coffee.

I'm not sure American is capable of on-time arrivals and departures. When you land at ORD, you almost always get held on the tarmac because your gate is still occupied. I may have missed my connection, but that ended up up being significantly delayed as well. Once again, I finally got home well after midnight.

Crew at the gate was very crabby and not at all polite. The plane was very hot the entire flight. And the seat cushion was very worn out.

The staff are very, very professional. It's what flying should feel like.

Flight was delayed half hour before boarding, but when I checked flight aware the plane that would Pick us up had a delay of more than an hour. AA should let us know in advance to avoid waiting several hours in the airport

Delays with no explanation. It could have been handled better.

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

Information on your arrival and departure airports