CHI - ASE

$172 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 8/23. 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 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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41,299,237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$342
Typical prices: $372-$527
American Airlines
Sun 7/26Tue 8/4
ORD - ASE • Non-stop
Cheapest one-way
$172
Typical prices: $278-$460
American Airlines
Sun 8/23
ORD - ASE • Non-stop
Top airlines
Cheapest • from $342 (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 American Airlines and United Airlines. Average duration is 3h 08m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Top routes
Cheapest
Most popular
Insights
Insights
Insights
Insights
Top layover airports
Cheapest • Avg $403 (round-trip)
Shortest trip • 4h 52m (one-way)
Insights
Insights
Insights
Insights
When to book
in advance
Our data shows that travelers who book at least 2 weeks in advance save around 35% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
Cheapest • 38% price drop
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Aspen!
Flight Deals
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Expert advice
Flight 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

Sun, Jul 26 - Tue, Aug 4
American Airlines Logo
7:49 pm - 9:56 pm
ORD
-
ASE
3h 07mnonstop
American Airlines Logo
7:25 am - 11:31 am
ASE
-
ORD
3h 06mnonstop
$342American Airlines
Sun, Aug 2 - Fri, Aug 7
American Airlines Logo
7:49 pm - 9:56 pm
ORD
-
ASE
3h 07mnonstop
American Airlines Logo
7:00 am - 11:06 am
ASE
-
ORD
3h 06mnonstop
$343American Airlines
Sun, Jul 26 - Tue, Aug 4
American Airlines Logo
5:00 am - 10:01 am
ORD
-
ASE
6h 01m
1 stop
American Airlines Logo
7:25 am - 11:31 am
ASE
-
ORD
3h 06mnonstop
$352American Airlines
Tue, Aug 4 - Wed, Aug 12
American Airlines Logo
8:30 am - 1:51 pm
ORD
-
ASE
6h 21m
1 stop
American Airlines Logo
1:54 pm - 6:07 pm
ASE
-
ORD
3h 13mnonstop
$353American Airlines
Sun, Jul 26 - Tue, Aug 4
American Airlines Logo
5:00 am - 10:01 am
ORD
-
ASE
6h 01m
1 stop
American Airlines Logo
7:25 am - 11:31 am
ASE
-
ORD
3h 06mnonstop
$354American Airlines
Tue, Sep 29 - Wed, Oct 7
Delta Logo
5:30 am - 11:21 am
ORD
-
ASE
6h 51m
1 stop
Delta Logo
8:05 am - 6:32 pm
ASE
-
ORD
9h 27m
1 stop
$363Delta
Tue, Sep 29 - Wed, Oct 7
Delta Logo
5:30 am - 11:21 am
ORD
-
ASE
6h 51m
1 stop
Delta Logo
8:05 am - 6:40 pm
ASE
-
ORD
9h 35m
2 stops
$368Delta
Tue, Jul 28 - Fri, Jul 31
United Airlines Logo
5:00 am - 8:46 am
ORD
-
ASE
4h 46m
1 stop
United Airlines Logo
5:10 pm - 10:49 pm
ASE
-
ORD
4h 39m
1 stop
$380United Airlines
Sun, Aug 2 - Fri, Aug 7
United Airlines Logo
5:00 am - 8:47 am
ORD
-
ASE
4h 47m
1 stop
United Airlines Logo
5:10 pm - 11:19 pm
ASE
-
ORD
5h 09m
1 stop
$389United Airlines
Fri, Aug 7 - Wed, Aug 12
Delta Logo
6:05 am - 11:23 am
MDW
-
ASE
6h 18m
1 stop
Delta Logo
7:20 am - 4:15 pm
ASE
-
MDW
7h 55m
1 stop
$484Delta
Booking Insights

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.

How much is a round-trip flight from Chicago to Aspen?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Chicago to Aspen departing in July.

What is the cheapest Chicago to Aspen flight route?

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

The cheapest return flight from Chicago to Aspen costs $343 on the route between Chicago O'Hare Intl Airport (ORD) and Aspen (ASE). It is also the most popular route.

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 Wednesday. On your return trip to Chicago, you should consider flying back on a Thursday, and avoid Mondays 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 June, where tickets cost $147 (return) on average. On the other hand, the most expensive months are April and November, where the average cost of round-trip tickets is $309 and $308 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.

No, with an average price for the route of $459, prices are generally cheapest when you fly direct.

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, which saves you about 35% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 11 weeks before departure.

Expert advice

Expert advice for your flight from Chicago to Aspen

 
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 seasonSeptember
Cheapest flight$172
Best time to beat the crowds with an average 23% drop in price.
Most popular time to fly with an average 5% 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 5 days, the lowest price for a flight from Chicago to Aspen was $172 for a one-way ticket and $342 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 Embraer 175 (Enhanced Winglets) 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 oneworld 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 $520 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 $410 and an overall rating of 7.1.

  • 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 $209 or less one-way and $459 or less round-trip.

Prefer to fly direct from Chicago to Aspen?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Chicago to Aspen Pitkin County.
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

Reviews of the 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 9896 reviews
7.3Comfort
7.7Boarding
7.1Entertainment
8.1Crew
6.6Food
Airline reviews

Great experience. Boarding was fast, staff were very nice and funny, everything at the seat worked well.

10.0 ExcellentNerissa, Jun 2026
ORD - ANC
Read more United Airlines reviews

Great experience. Boarding was fast, staff were very nice and funny, everything at the seat worked well.

Horrible! Several delays and then was cancelled! I spent over 24 hours in the airport and was unable to get a hotel or food voucher.

Boarded early; and arrived home 40 mins early. After a long flight, it’s nice to be back home early. These flights have no amenities; no snacks. So need to bring your own

It was a short flight so I was expecting too much

A long delay. Don't travel late in the day.

Super friendly with lots of drink options an entertainment. Friendly crew.

The crew was great. Very friendly and responsive. The plane was old, small and tight. We ran out of overhead space and I had to check. Middle seat was particularly tight.

Excellent flight. Boarding was efficient and departure was on time. Smooth flight with on time arrival. Deplaning was also efficient.

late departure due to some unspecified issue with ventilating the cabin. They got it running but it was FREEZING for the whole flight. I asked for a blanket but they didn't provide one. They could not turn up the heat. it was quite miserable.

Plane was so old it had cigarette butt trays in the seat

Very turbulent flight, no drinks, very little service, unorganized boarding, gate changed multiple times

The flight was delayed significantly. Communication during the flight was abrupt and caused some panic as we were navigating turbulence. It was also too loud and every announcement felt startling. The flight attendants did not offer any assurances and I felt unsettled most of the flight. The seats, floor and tray table was very dirty. The seat next to me was broken and the passenger sitting there was very uncomfortable. He had a spring in his back and his seat made terrible squeaking noises through the flight.

Significant delays on my trip to Chicago and my trip back to NY

Delayed by 5 hours and I had to wit in the airport for more than 6+ hours.

I’ve got 31F seat and window seat . My 2 co passengers was AA crew members and they were very rude attitude and when I was going to use bathroom their gestures was very different and awkward and the guy beside me completely occupied the hand rest and I was really uncomfortable

It was so much better than expected, Ohare is not such a pleasant experience but American Airlines with the new, clean aeroplane and free Wi-Fi was outstanding and the crew so pleasant and helpful.

It wa sort of on time; the cab was left with some trash

Because the plane was 90 degrees F, they would not let us board. I wish they had, because it meant we were delayed. It's Texas, of course it's hot. We would have survived.

WiFi was down so no entertainment and I could not work either. The flight was Very turbulent at the end (the last 20 min felt like an eternity) I appreciated the pilot for getting us there safely. The flight attending in first class was kind and attentive to everyone.

Because I can’t stand very long in one place, I was allowed to reword.

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

Information on your arrival and departure airports