ASE - CHI

$211 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 2/27. 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
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$311
Typical prices: $384-$506
American Airlines
Wed 3/11Mon 3/16
ASE - ORD • Non-stop
Cheapest one-way
$211
Typical prices: $587-$788
American Airlines
Fri 2/27
ASE - ORD • Non-stop
Our travelers' advice
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
American Airlines
Cheapest • from $311 (round-trip)
United Airlines
Best reviews • 7.4 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Top routes
ASE
-
ORD
Cheapest
ASE
-
ORD
Most popular
Insights
Insights
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Insights
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
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

Wed, Mar 11 - Mon, Mar 16
American Airlines Logo
3:46 pm - 7:47 pm
ASE
-
ORD
3h 01mnonstop
American Airlines Logo
7:15 am - 9:37 am
ORD
-
ASE
3h 22mnonstop
$311American Airlines
Wed, Apr 1 - Tue, Apr 7
American Airlines Logo
3:46 pm - 7:47 pm
ASE
-
ORD
3h 01mnonstop
American Airlines Logo
10:30 pm - 12:28 pm
ORD
-
ASE
14h 58m
2 stops
$313American Airlines
Wed, Mar 11 - Mon, Mar 16
American Airlines Logo
11:33 am - 8:04 pm
ASE
-
ORD
7h 31m
1 stop
American Airlines Logo
10:18 am - 12:49 pm
ORD
-
ASE
3h 31mnonstop
$321American Airlines
Wed, Apr 1 - Tue, Apr 7
American Airlines Logo
2:47 pm - 10:24 pm
ASE
-
ORD
6h 37m
1 stop
American Airlines Logo
10:30 pm - 12:28 pm
ORD
-
ASE
14h 58m
2 stops
$328American Airlines
Wed, Mar 11 - Mon, Mar 16
American Airlines Logo
11:33 am - 9:05 pm
ASE
-
ORD
8h 32m
1 stop
American Airlines Logo
5:00 am - 11:49 am
ORD
-
ASE
7h 49m
1 stop
$331American Airlines
Wed, Mar 11 - Mon, Mar 16
American Airlines Logo
4:36 pm - 11:36 pm
ASE
-
ORD
6h 00m
1 stop
American Airlines Logo
5:00 am - 11:49 am
ORD
-
ASE
7h 49m
1 stop
$341American Airlines
Thu, Mar 12 - Thu, Mar 19
American Airlines Logo
1:24 pm - 5:25 pm
ASE
-
ORD
3h 01mnonstop
American Airlines Logo
12:24 pm - 2:52 pm
ORD
-
ASE
3h 28mnonstop
$356American Airlines
Tue, Mar 3 - Fri, Mar 6
American Airlines Logo
1:24 pm - 5:25 pm
ASE
-
ORD
3h 01mnonstop
American Airlines Logo
7:10 am - 9:32 am
ORD
-
ASE
3h 22mnonstop
$372American Airlines
Tue, Mar 3 - Fri, Mar 6
Delta Logo
3:00 pm - 10:33 pm
ASE
-
MDW
6h 33m
1 stop
Delta Logo
6:00 am - 2:14 pm
MDW
-
ASE
9h 14m
1 stop
$755Delta
Wed, Apr 1 - Tue, Apr 7
Delta Logo
1:45 pm - 10:31 pm
ASE
-
MDW
7h 46m
1 stop
Delta Logo
6:00 am - 2:13 pm
MDW
-
ASE
9h 13m
1 stop
$895Delta
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 $248 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 Thursday and avoid Mondays if you are looking for the best rates. For your return to Aspen, you’ll find the best rates on Sundays 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 $311, 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

Low seasonApril
Cheapest flight$211
Best time to beat the crowds with an average 24% drop in price.
Most popular time to fly and prices are also 8% lower on average.
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

  • 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 $211 for a one-way ticket and $311 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?

    American Airlines, and Delta offer inflight Wi-Fi service on the Aspen to Chicago flight route.

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

    The Canadair (Bombardier) Regional Jet 700 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 $384 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 $349 and an overall rating of 7.2.

  • 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 $320 or less one-way and $319 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

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

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

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 9212 reviews
7.1Entertainment
7.3Comfort
8.1Crew
7.7Boarding
6.6Food
Airline reviews

Seated dude next to me even though lots of empty rows. But main thing was we sat on the tarmac after landing for 30 minutes because of, in the words of the dude who sat next to me, “operational incompetence”. We got changing directions about where to pick up gate checked bags. Pilot and flight attendant were awesome though.

4.0 OkaySean, Jan 2026
BOS - ORD
Read more United Airlines reviews

Seated dude next to me even though lots of empty rows. But main thing was we sat on the tarmac after landing for 30 minutes because of, in the words of the dude who sat next to me, “operational incompetence”. We got changing directions about where to pick up gate checked bags. Pilot and flight attendant were awesome though.

It was a pretty standard flight... until the almost hour and a half spent on the taxi way. I get that the weather has been poor but the delay had nothing to do with the weather and more to do with a plane with several issues tying up the gate. I get that that happens from time to time but this has been EVERY flight I've been on for the past 5 years and I fly 3 to 5 times a year. This isn't just United... it's American, it's Delta. It's an issue with the entire industry. I work for UPS and packages on a cargo plane get better service than people do these days. Anymore I HATE flying.

Perfect flight. Smooth flight. Arrived 20 minutes early at destination. Excellent service.

The flights were on time which was great give. It was holiday travel season and there’d been some weather issues. The only complaint and this is every time with United is the terrible seat design. The head rest is not built for comfort and having my neck bent forward for a cross country trip reminded me while I try not to take United flights as a rule.

Everything was absolutely wonderful from check in to baggage claim. Staff was very professional and sweet. Will definitely recommend United to family and friends.

They did the one thing that really matters - got to Chicago early.

The flight was on time. I generally don’t drink or eat on short flights and the seats were good and the flight attendants were friendly. That’s all I expect

It was nice to have gotten up upgraded to first class with a meal on a three hour flight

Very bad! They kept delaying my flight and wouldn’t do anything about it

Door to door, the crew and staff were amazing. It was a stressful travel day with delays, but they were focused on customers and doing what they could to get us to our destinations.

Pilot navigated severe weather/snow storm with skill. Described his intentions clearly

Little warm on the plane and delayed for an hour

So excited very proud first of all I wanna thank kayak all updates very professional and fast alart And amazing cabin crew so nice to me they deserve big salute

The boarding process needs to be fixed. The zone don't work, especially when there is hardly anyone in zones 3, 4,and 5, leaving the majority of the passengers backed up in the aisle, especially because passengers seated near the front are blocking passengers who are seated in the rear of the plane. It would also help if the size of carry on bags was more strictly enforced.

Awful. They won’t help me with anything. I booked on American but they abdicated to Iberia. The ticket was overpriced. Everything negative

I enjoyed the extra leg room compared to other airlines. The first stewards made my daughter’s birthday special by giving her an extra snack. Then the last one coming home from Chicago to Appleton made our night really enjoyable Thanks for making our trip enjoyable

It was good..clean, comfy seat. Friendly warm welcoming crew. Was able to check my cabin luggage at the gate which I was able to pickup in a decent time from baggage claim. The app gave all updates from delays to baggage claim info. Overall smooth flight.

It was a typical flight. We had a delay which seems to be the normality now. And we had no in flight service due to conditions.

After we landed we sat on the tarmac for 1.5 hours waiting to get to our gate. Ridiculous.

Terrible. Flight delayed for more than 8 hours with only a $12 meal voucher provided for the inconvenience. The airplane did not have breaks on arrival yet they still made us go through the motions and board on time knowing we could not take off then sit for 40+ minutes before having to get of the time. A complete waste of my time. I cannot believe they can stay business with these shenanigans. I’ll avoid this company like the plague moving forward as the lack of accountability is disgraceful.

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

Information on your arrival and departure airports