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 7/30. 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

Save 24% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Everything you should know

Cheapest round-trip
$343
Typical prices: $618-$383
American Airlines
Fri 7/3Mon 7/6
ASE - ORD • Non-stop
Cheapest one-way
$172
Typical prices: $320-$511
American Airlines
Thu 7/30
ASE - ORD • Non-stop
Top airlines
American Airlines
Cheapest • from $343 (round-trip)
United Airlines
Best reviews • 7.4 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
Every day
You can fly direct with American Airlines and United Airlines. Average duration is 3h 04m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Top routes
ASE
-
ORD
Cheapest
ASE
-
ORD
Most popular
Insights
Insights
Insights
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
Booking Insights
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

Fri, Jul 3 - Mon, Jul 6
American Airlines Logo
7:25 am - 11:31 am
ASE
-
ORD
3h 06mnonstop
American Airlines Logo
7:49 pm - 9:56 pm
ORD
-
ASE
3h 07mnonstop
$343American Airlines
Fri, Jul 3 - Mon, Jul 6
American Airlines Logo
7:25 am - 11:31 am
ASE
-
ORD
3h 06mnonstop
American Airlines Logo
7:00 am - 12:21 pm
ORD
-
ASE
6h 21m
1 stop
$353American Airlines
Thu, Aug 20 - Tue, Aug 25
Delta Logo
7:20 am - 4:15 pm
ASE
-
MDW
7h 55m
1 stop
Delta Logo
6:05 am - 11:23 am
MDW
-
ASE
6h 18m
1 stop
$363Delta
Fri, Jul 3 - Mon, Jul 6
American Airlines Logo
10:31 am - 8:29 pm
ASE
-
ORD
8h 58m
1 stop
American Airlines Logo
5:00 am - 12:21 pm
ORD
-
ASE
8h 21m
1 stop
$363American Airlines
Fri, Oct 16 - Sun, Oct 18
United Airlines Logo
1:00 pm - 5:00 pm
ASE
-
ORD
3h 00mnonstop
United Airlines Logo
8:45 am - 11:04 am
ORD
-
ASE
3h 19mnonstop
$366United Airlines
Thu, Jul 23 - Sun, Jul 26
United Airlines Logo
5:10 pm - 10:49 pm
ASE
-
ORD
4h 39m
1 stop
United Airlines Logo
7:47 pm - 10:00 pm
ORD
-
ASE
3h 13mnonstop
$376United Airlines
Wed, Aug 19 - Sun, Aug 23
American Airlines Logo
1:54 pm - 6:07 pm
ASE
-
ORD
3h 13mnonstop
American Airlines Logo
11:16 am - 1:24 pm
ORD
-
ASE
3h 08mnonstop
$381American Airlines
Thu, Jul 2 - Sun, Jul 5
American Airlines Logo
7:25 am - 11:31 am
ASE
-
ORD
3h 06mnonstop
American Airlines Logo
11:15 am - 1:21 pm
ORD
-
ASE
3h 06mnonstop
$382American Airlines
Wed, Aug 19 - Sun, Aug 23
Delta Logo
7:20 am - 4:15 pm
ASE
-
MDW
7h 55m
1 stop
Delta Logo
6:05 am - 11:23 am
MDW
-
ASE
6h 18m
1 stop
$391Delta
Wed, Aug 19 - Sun, Aug 23
Delta Logo
7:20 am - 4:51 pm
ASE
-
ORD
8h 31m
1 stop
Delta Logo
5:28 am - 11:23 am
ORD
-
ASE
6h 55m
1 stop
$391Delta
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 $343 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 Tuesdays and the most expensive ones on Thursdays.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Aspen to Chicago, 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 Aspen to Chicago is March, where tickets cost $0 (return) on average. On the other hand, the most expensive months are December and February, where the average cost of round-trip tickets is $646 and $505 respectively.

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 $396, prices are generally cheapest when you fly direct.

Find deals
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
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.

Read more
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.

Read more

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

  • What is the cheapest flight from Aspen to Chicago?

    In the last 5 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.

  • 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 $279 or less one-way and $432 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 airline 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 9775 reviews
7.1Entertainment
8.1Crew
7.3Comfort
7.7Boarding
6.6Food
Airline reviews

Boarded early, left early, arrived 40 mins early! A win win for me!

10.0 ExcellentJanice, Jun 2026
IAH - ORD
Read more United Airlines reviews

Boarded early, left early, arrived 40 mins early! A win win for me!

These airplanes should be illegal. The seats are two tight, it is a safety issue. Wheelchair support was ridiculously slow. We almost missed our flight.

This flight is a quick way to get to Chicago, but a bit expensive.

O’hsre taxi and deboarding took 40 minutes. Needed 20 minutes extra time between connecting flights to avoid running through terminal.

Standard flight with a drinks and a snack- overall very quick flight. The flight attendants were very strict, bordered on rude.

Delayed - weather wasn't bad at either end. Also sat on tarmac in ORD.

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.

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

Information on your arrival and departure airports

Aspen (ASE)