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ASE - CHI

Find cheap flights from Aspen to Chicago from $230

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 7/17. 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
0 bags
Fri 5/24
Fri 5/31

Search 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
In the last 7 days travelers have searched 44,632,927 times on KAYAK, and here is why:

Save 22% or moreCompare multiple travel sites with one search.

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

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

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

Cheap flight deals 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 and deals for you by selecting your travel dates.
Choose your dates
11:23 am - 3:14 pmASE-ORD
2h 51mnonstop
7:45 pm - 9:45 pmORD-ASE
3h 00mnonstop
$331United Airlines
Find Deal
Wed, Jul 17 - Wed, Jul 17
12:21 pm - 4:15 pmASE-ORD
2h 54mnonstop
9:50 am - 11:48 amORD-ASE
2h 58mnonstop
$351American Airlines
Find Deal
Fri, Aug 30 - Mon, Sep 2
7:54 am - 3:50 pmASE-MDW
6h 56m1 stop
6:00 am - 11:42 amMDW-ASE
6h 42m1 stop
$360Delta
Find Deal
Wed, May 29 - Wed, Jun 5
7:54 am - 4:47 pmASE-ORD
7h 53m1 stop
5:40 am - 11:42 amORD-ASE
7h 02m1 stop
$360Delta
Find Deal
Tue, May 28 - Wed, Jun 5
12:20 pm - 4:10 pmASE-ORD
2h 50mnonstop
10:05 am - 12:07 pmORD-ASE
3h 02mnonstop
$361American Airlines
Find Deal
Wed, Jun 5 - Sat, Jun 8
7:54 am - 3:50 pmASE-MDW
6h 56m1 stop
6:00 am - 11:42 amMDW-ASE
6h 42m1 stop
$370Delta
Find Deal
Wed, May 29 - Sun, Jun 2
4:15 pm - 11:41 pmASE-ORD
6h 26m1 stop
10:05 am - 12:07 pmORD-ASE
3h 02mnonstop
$370American Airlines
Find Deal
Wed, Jun 5 - Sat, Jun 8
7:54 am - 2:55 pmASE-MDW
6h 01m1 stop
6:00 am - 11:42 amMDW-ASE
6h 42m1 stop
$380Delta
Find Deal
Sun, May 26 - Wed, Jun 5
9:15 am - 1:07 pmASE-ORD
2h 52mnonstop
2:36 pm - 6:28 pmORD-ASE
4h 52m1 stop
$408United Airlines
Find Deal
Wed, Jul 17 - Wed, Jul 17
9:08 am - 1:00 pmASE-ORD
2h 52mnonstop
7:40 pm - 9:37 pmORD-ASE
2h 57mnonstop
$421United Airlines
Find Deal
Tue, May 28 - Thu, Jun 6

Flights from Aspen to Chicago - Travel Insights & Trends

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?

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for one-way flights from Aspen to Chicago.
Our data shows that the cheapest route for a one-way flight from Aspen to Chicago cost $287 and was between Aspen and Chicago O'Hare Intl Airport. On average, the best prices are found if you fly this route. The average price for a return flight for this route is $359.

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

The average price of all flights from Aspen to Chicago clicked on KAYAK for each day over the last 12 months.
If you are looking for a flight deal from Aspen to Chicago, look for departures on Tuesdays and avoid leaving on a Friday, as it's usually the priciest day. When flying back from Chicago, Sunday is the cheapest day to fly and Thursday is the most expensive.

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 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 December, where tickets cost $399 on average. On the other hand, the most expensive months are April and July, where the average cost of tickets is $805 and $730 respectively.

Which airlines provide the cheapest flights from Aspen to Chicago?

The cheapest price for the route for each airline clicked by KAYAK users in the last 72 hours.
The cheapest return flight ticket from Aspen to Chicago found by KAYAK users in the last 72 hours was for $331 on United Airlines, followed by American Airlines ($351). One-way flight deals have also been found from as low as $230 on United Airlines and from $368 on American Airlines.

Which airlines fly non-stop between Aspen and Chicago?

Airline and price data is aggregated from results in KAYAK’s search results from the last 2 weeks for flights from Aspen to Chicago.
There is just one airline that flies from Aspen to Chicago direct and that is United Airlines. The best one-way deal found from United Airlines for the route is $363.

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

Each day, there are between 2 and 3 nonstop flights that take off from Aspen and land in Chicago, with an average flight time of 2h 51m. The most common departure time is 9:00 am and most flights take off in the morning, while the most flights land at Chicago O'Hare Intl Airport. Each week, there are 18 flights. The most frequent day of departure is Sunday, when 17% of all weekly flights depart. The fewest flights depart on a Tuesday.

Which cabin class options are there for flights between Aspen and Chicago?

The average price of flights for each cabin class for the route found by users searching on KAYAK over the last 2 weeks.
There are 4 cabin class options for the route. These are First, Business, Economy and Prem Economy. Perform a search on KAYAK to find the latest prices and availability for all cabin fares, which differ across airlines.

How long does a flight from Aspen to Chicago take?

A direct flight to Chicago will take on average 2h 50m to travel the 1,024 miles flying distance from Aspen.

What’s the earliest departure time from Aspen to Chicago?

Early birds can take the earliest flight from Aspen at 9:08 am and will be landing in Chicago at 1:00 pm.

What’s the latest departure time from Aspen to Chicago?

If you prefer to fly at night, the latest flight from Aspen to Chicago jets off at 1:15 pm and lands at 5:05 pm.

Good to know

Low season

May

High season

September

Cheapest flight

$230
Best time to beat the crowds with an average 2% drop in price.
Most popular time to fly and prices are also 23% 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 $230 for a one-way ticket and $331 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 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?

    Star Alliance is the only airline alliance operating flights between Aspen and Chicago.

  • 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 $489 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 $420 and an overall rating of 7.3.

  • 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.

See more FAQs

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 $389 or less one-way and $454 or less round-trip.

Prefer to fly non-stop from Aspen to Chicago?

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

Nonstop departures

Aspen Pitkin County to Chicago

Monday

Lufthansa, United Airlines, American Airlines, +1 more

Lufthansa, United Airlines, +2 more

Tuesday

Lufthansa, United Airlines, American Airlines, +1 more

Lufthansa, United Airlines, +2 more

Wednesday

Lufthansa, United Airlines, American Airlines, +1 more

Lufthansa, United Airlines, +2 more

Thursday

Lufthansa, United Airlines, American Airlines, +1 more

Lufthansa, United Airlines, +2 more

Friday

Lufthansa, United Airlines, American Airlines, +1 more

Lufthansa, United Airlines, +2 more

Saturday

Lufthansa, United Airlines, American Airlines, +1 more

Lufthansa, United Airlines, +2 more

Sunday

Lufthansa, United Airlines, American Airlines, +1 more

Lufthansa, United Airlines, +2 more

See more direct flights

Nonstop returns

Chicago to Aspen Pitkin County

Monday

Lufthansa, United Airlines, American Airlines

Lufthansa, United Airlines, +1 more

Tuesday

Lufthansa, United Airlines, American Airlines

Lufthansa, United Airlines, +1 more

Wednesday

Lufthansa, United Airlines, American Airlines

Lufthansa, United Airlines, +1 more

Thursday

Lufthansa, United Airlines, American Airlines

Lufthansa, United Airlines, +1 more

Friday

Lufthansa, United Airlines, American Airlines

Lufthansa, United Airlines, +1 more

Saturday

Lufthansa, United Airlines, American Airlines

Lufthansa, United Airlines, +1 more

Sunday

Lufthansa, United Airlines, American Airlines

Lufthansa, United Airlines, +1 more

See more direct flights
See more direct flights

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 11272 reviews
7.2comfort
7.7boarding
7.1entertainment
8.1crew
6.7food
Airline reviews

The delays (5 hrs) were a comedy of errors, and the multiple safety issues encountered were very concerning.

2.0 MediocreMichelle, Apr 2024ELP - ORD
Read more about United Airlines reviews

The delays (5 hrs) were a comedy of errors, and the multiple safety issues encountered were very concerning.

The flight was delayed instead of leaving at 11 it left at 12.20

United WiFi is consistently unusable (it can take 10 mins to load a single web page). If you need Wifi to do work, be prepared to lose half a day of productivity.

Good movies, iffy pay WiFi, food ok- on time though and that was great!

Awful…flight was delayed more than 12hrs, missed all connections to Fort Wayne, IN, had to get flight to another city 2 hours from my destination, flight was again delayed by 40 mins because they did not have enough fuel, again missed a connection, finally arrived in Indiana at 11pm…but before my 2 hour drive home, ay, no Five That Our Luggage Never Made On The plane and Still In Chicago

Boarding was friendly and quick. While the plane model was older with no live tv, the entertainment was full of movies and tv shows. All food was available. Pilots were very communicative with status of the flight. Flight landed on time.

The Palm Springs to Chicago O’Hare was on Time and Palm Springs airport is easier navigate. As our connection was only an approximately 50 minutes, we asked staff for insights for the Chicago airport in terms of transferring into the other terminal from which our flight left, and they were unhelpful. However, the United App was very helpful in terms of notifications and even providing directions. The Chicago to Detroit flight was significantly delayed which we all know does happen. However, there were very few updates or notifications as to why this was happening when we would actually arrive. It took nearly 30 minutes for bags to make it to baggage claim. We arrived nearly 1 hour late on a 40 minute flight.

Flight cancelled due to fog. No other flights available for 36 hours. Directed by United to book passage on another carrier, and submit receipts for reimbursement. Did that. United now states they will not reimburse. Currently out 2 grand.

The flight was delayed by 4 hours !!!!! It was very uncomfortable , and they told us only one our before departure

The flights from Ottawa to Albuquerque went smoothly enough though on on flight they didn't have how water for coffee or tea and on another there there was no ice. The return flights from Albuquerque were delayed by mechanical problems on both flights. Ottawa was a ground crew maintenance issue.

This flight is frequently delayed. The connections seemingly are more frequently delayed. I’ve missed connections as a result twice on the same route to charlotte then Charleston. Final destination arrival has been the next day, twice in a row. No pilots, no crew. Too many excuses. Unfortunately, my days with American are over.

Entertainment was okay not because anything was wrong but it is a short flight so having no wifi is annoying but understandable. Crew was outstanding as usual

Those seats were way too narrow. I had the middle seat, one person was a very skinny person and we still couldn’t avoid touching each other anytime one of us moved. The other person was larger and we were basically sitting in each others lap the entire flight. There was zero entertainment. The flight was long enough to justify tvs, but no. Gotta sit there in your infant seat and twiddle your thumbs.

Flight was fine. It took an unusually long time to have baggage delivered to the carousel in ORD.

Average - flew with Jet Blue internal and it was far more comfortable and better food and entertainment. Notable difference

The flight got canceled due to mechanical issues, and he to be rebooked and missed my appointments for that day

The flight was scheduled to depart DCA at 12:30 pm but was delayed twice on the ground so that we were finally scheduled to depart at around 4:00 pm. Once we boarded, it was announced that takeoff would be delayed again to fix a hydraulic problem which delayed our eventual takeoff until around 5:00 pm. Once we departed, it was a smooth flight back to ORD. We did not get any explanation about what caused the original significant delay. In my experience, this happens frequently with AA.

The only problem experienced was a ground stop in Chicago due to weather. But the crew handled everything professionally. They prioritized rebooking those passengers who had connecting flights and then deplaning the other passengers. When the hold was lifted, they efficiently re-boarded all the passengers so that we could depart before our departure limit expired.

Our second leg to Jackson WY was unable to land due to weather. We were flown back to Dallas after stopping in SLC. We were given hotel rooms and vouchers. We were told that we would be back on the same plane in the morning. Instead we were given a different flight with different seats. Not a good experience. No one knew what was going on.

Turn on the heat. Flight was way too cold from Arizona to Chicago.

Book cheap flights from Aspen to Chicago

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from Aspen to Chicago found on KAYAK in the last 72 hours.
7/17Wed
nonstopUnited Airlines
2h 52mASE-ORD
$230
7/17Wed
1 stopUnited Airlines
5h 31mASE-ORD
$239
8/9Fri
nonstopUnited Airlines
2h 51mASE-ORD
$270
8/9Fri
1 stopUnited Airlines
7h 27mASE-ORD
$279
8/9Fri
2 stopsUnited Airlines
14h 11mASE-ORD
$339
7/14Sun
1 stopAmerican Airlines
5h 40mASE-ORD
$368
8/9Fri
1 stopDelta
6h 12mASE-MDW
$418
7/17Wed
1 stopDelta
6h 04mASE-MDW
$469
7/17Wed
2 stopsDelta
9h 36mASE-MDW
$624
7/14Sun
2 stopsAmerican Airlines
17h 25mASE-ORD
$683

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Aspen - Chicago Flights

Departure:

Aspen (ASE)United States

Return flight deals:

Chicago - Aspen

Cabin classes:

$819
$1,745
$359