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Aspen

$211+ Cheap flights from Chicago (CHI) to Aspen (ASE)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 1/1. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — ASE
Jan 11 — Jan 181
Sun 1/11
Sun 1/18
1 adult, Economy
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1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

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Cheapflights Tip: The best prices from Chicago to Aspen Pitkin County are usually found in September or November, booked 62 days in advance, depart on a Tuesday or Monday and return on a Thursday

Cheap flight deals from Chicago to Aspen

Cheapest flights from Chicago to Aspen
Explore the most affordable flight options available from Chicago to Aspen. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 12, 2025.

This American Airlines deal was found by Cheapflights users on 12/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/307:10 amORD - ASE
Nonstop3h 41mAmerican Airlines
Wed 1/712:54 pmASE - ORD
Nonstop3h 01mAmerican Airlines
Deal found 12/9$311
This United Airlines deal was found by Cheapflights users on 12/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/318:45 amORD - ASE
Nonstop3h 37mUnited Airlines
Mon 1/55:00 pmASE - ORD
1 stop5h 00mUnited Airlines
Deal found 12/11$424
This American Airlines deal was found by Cheapflights users on 12/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/2311:46 amORD - ASE
Nonstop3h 30mAmerican Airlines
Fri 12/262:53 pmASE - ORD
Nonstop3h 20mAmerican Airlines
Deal found 12/9$431
This United Airlines deal was found by Cheapflights users on 12/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/258:45 amORD - ASE
Nonstop3h 37mUnited Airlines
Mon 12/294:15 pmASE - ORD
Nonstop3h 05mUnited Airlines
Deal found 12/9$439
This United Airlines deal was found by Cheapflights users on 12/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/304:47 pmORD - ASE
Nonstop3h 30mUnited Airlines
Wed 1/75:02 pmASE - ORD
2 stops13h 43mUnited Airlines
Deal found 12/9$455
This Delta deal was found by Cheapflights users on 12/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/306:00 amMDW - ASE
1 stop9h 15mDelta
Wed 1/73:04 pmASE - MDW
1 stop6h 03mDelta
Deal found 12/9$915
This Delta deal was found by Cheapflights users on 12/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/256:00 amMDW - ASE
1 stop6h 39mDelta
Sun 12/281:20 pmASE - MDW
1 stop8h 02mDelta
Deal found 12/9$1,399

Find flight deals from Chicago to Aspen

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Aspen (ASE). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated December 12, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$227
(American Airlines)

One-way from

$211
(United Airlines)

Popular in

February

Cheapest in

September

Average price

$640

Good round-trip deal

$349 or less

Good one-way deal

$428 or less
Provider with most accurate pricing for Chicago (CHI)-Aspen Pitkin County flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Aspen Pitkin County flights.
Search Deals
From Chicago (CHI) to Aspen Pitkin County
Search Deals
One-way flight from Chicago (CHI) to Aspen Pitkin County
Search Deals
Highest demand for flights based on searches. 8% potential increase in price ($51 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($11 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals
Price to beat on a round-trip flight from Chicago (CHI) to Aspen Pitkin County.
Search Deals
Price to beat on a one-way flight from Chicago (CHI) to Aspen Pitkin County.
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to Aspen that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated December 12, 2025.
Use the filters below to find and compare flights from Chicago to Aspen that are best for you.

Fly from

Chicago

Fly to

Aspen

Route

Depart

Return

Price

ChicagoAspen

ORD - ASE

ORDASE

Chicago O'Hare Intl

Tue 1/20

9:18 am-11:55 am

Nonstop3h 37m

Aspen Pitkin County

Fri 1/23

4:01 pm-8:06 pm

Nonstop3h 05m

$311

ChicagoAspen

ORD - ASE

ORDASE

Chicago O'Hare Intl

Mon 3/2

9:00 am-11:41 am

Nonstop3h 41m

Aspen Pitkin County

Thu 3/5

6:28 pm-11:52 pm

1 stop4h 24m

$321

ChicagoAspen

MDW - ASE

MDWASE

Chicago Midway

Tue 1/20

6:00 am-2:16 pm

1 stop9h 16m

Aspen Pitkin County

Fri 1/23

3:04 pm-10:22 pm

1 stop6h 18m

$331

ChicagoAspen

MDW - ASE

MDWASE

Chicago Midway

Tue 1/13

6:45 am-2:16 pm

1 stop8h 31m

Aspen Pitkin County

Wed 1/21

3:04 pm-10:22 pm

1 stop6h 18m

$331

ChicagoAspen

MDW - ASE

MDWASE

Chicago Midway

Tue 2/17

6:00 am-2:14 pm

1 stop9h 14m

Aspen Pitkin County

Wed 2/25

2:55 pm-10:42 pm

1 stop6h 47m

$331

ChicagoAspen

MDW - ASE

MDWASE

Chicago Midway

Tue 1/13

6:45 am-2:16 pm

1 stop8h 31m

Aspen Pitkin County

Thu 1/22

1:34 pm-10:22 pm

1 stop7h 48m

$331

ChicagoAspen

MDW - ASE

MDWASE

Chicago Midway

Tue 2/10

6:00 am-2:16 pm

1 stop9h 16m

Aspen Pitkin County

Fri 2/13

1:32 pm-10:42 pm

1 stop8h 10m

$331

ChicagoAspen

ORD - ASE

ORDASE

Chicago O'Hare Intl

Tue 1/13

5:30 am-11:43 am

1 stop7h 13m

Aspen Pitkin County

Wed 1/21

3:04 pm-11:56 pm

1 stop7h 52m

$331

ChicagoAspen

ORD - ASE

ORDASE

Chicago O'Hare Intl

Tue 1/20

5:30 am-2:16 pm

1 stop9h 46m

Aspen Pitkin County

Fri 1/23

1:34 pm-11:55 pm

1 stop9h 21m

$331

ChicagoAspen

ORD - ASE

ORDASE

Chicago O'Hare Intl

Sun 1/11

5:30 am-11:43 am

1 stop7h 13m

Aspen Pitkin County

Thu 1/15

3:04 pm-11:59 pm

1 stop7h 55m

$331

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/11

Showing 1-10 of 34 results
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Compare providers for flights from Chicago to Aspen

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Chicago to Aspen in December.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Chicago-Aspen flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Chicago-Aspen flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Chicago-Aspen flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago-Aspen flights, Cheapflights users trust eDreams the most. eDreams has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago-Aspen flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Chicago to Aspen

Have a flexible travel schedule? Discover the best time to fly to Aspen from Chicago with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

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

How far ahead should I book a flight from Chicago to Aspen?

Use this chart to determine the optimal time to book a round-trip flight from Chicago to Aspen. Price data was last updated on December 5, 2025.

To ensure you get the cheapest price possible for a flight from Chicago to Aspen, you should look to book at least 62 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

What is the cheapest month to book a flight from Chicago to Aspen?

Currently, February is the cheapest month in which you can book a flight from Chicago to Aspen (average of $128). Flying from Chicago to Aspen in April is currently the most expensive (average of $344). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from CHI to ASE?

Find hourly flight availability from Chicago to Aspen. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated December 12, 2025.

One of the essential ways to save on airfare from Chicago to Aspen is to remain as flexible as possible. Flights that are in the morning tend to be the most expensive. A flight in the evening could potentially save you up to 43% on airfare.

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

Use this chart to determine the cheapest time to fly round-trip from Chicago to Aspen. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Chicago to Aspen flight should consider departing on Monday evenings when fares are most often at their lowest. Saturday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from Chicago to Aspen

Explore weekly flight availability from Chicago to Aspen. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated December 12, 2025.

The most flights from CHI to ASE are scheduled on a Monday (3 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (3 on average).

Reviews of airlines servicing Aspen

Get insights into the airlines that provide service to Aspen. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Aspen. Reviews last updated December 12, 2025.
Read reviews from past customers who have flown United Airlines and American Airlines from Chicago to Aspen. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
9,095 reviews

Food

6.6

Comfort

7.3

Crew

8.1

Entertainment

7.1

Boarding

7.7

Overall

7.4

Reviews

1 / 20
10.0
Excellent

Julia,Sep 2025

BUF - DEN

The staff were amazing, from check in to boarding and on the flight. The range of entertainment options were really good as well.
United Airlines
7.4
Good
9,095 reviews
United Airlines
7.4
Good
9,095 reviews

Food

6.6

Comfort

7.3

Crew

8.1

Entertainment

7.1

Boarding

7.7

Overall

7.4

Reviews

1 / 20
10.0
Excellent

Julia,Sep 2025

BUF - DEN

The staff were amazing, from check in to boarding and on the flight. The range of entertainment options were really good as well.
American Airlines
7.2
Good
11,050 reviews
United Airlines
7.4
Good
9,095 reviews

Food

6.6

Comfort

7.3

Crew

8.1

Entertainment

7.1

Boarding

7.7

Overall

7.4

Reviews

1 / 20
10.0
Excellent

Julia,Sep 2025

BUF - DEN

The staff were amazing, from check in to boarding and on the flight. The range of entertainment options were really good as well.

Related info for your journey

Find useful and relevant information for your journey from Chicago to Aspen. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to Aspen from Chicago?

    Aspen Pitkin County (ASE), located 3.5 mi from the city center, is the airport you fly into when you book flights from Chicago to Aspen. 2 airlines have flights to Pitkin County from Chicago on a regular basis. Booking flights from Chicago to Aspen Pitkin County should not be difficult; the airport handles an average of 3 inbound flights from Chicago per day.

  • How long is the flight from Chicago to Aspen?

    There are many flights that can get you from Chicago to Aspen in 3h 37m. Fly via United Airlines or Delta to get the fastest option. Chicago and Aspen are separated by a distance of 1010 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What are the cheapest airlines flying from Chicago to Aspen round-trip?

    Our cheapest airline available from Chicago to Aspen is American Airlines. Our recent data shows that you can find tickets from as low as $239 on this airline. An additional option worth looking into is United Airlines, starting at $299. American Airlines is currently priced 55% below the average price you’ll pay for this route.

  • What are the most reliable airlines from Chicago to Aspen?

    Looking for the most reliable airlines to get you to your destination on time? Our data shows these are most likely to get you from Chicago to Aspen on time: Lufthansa (83%), United Airlines (70%), SkyWest Airlines (55%).

  • What are the cheapest flights from Chicago to Aspen?

    While on average a flight from Chicago to Aspen is generally $461, our data shows the cheapest flight currently is $303. When looking at the most popular route, (Chicago O'Hare Intl - Aspen Pitkin County), you can expect to pay $311 for that flight.

  • Can I find deals for flights from Chicago to Aspen that include hotel bookings?

    Yes. In addition to deals on Chicago to Aspen flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Aspen?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Aspen.

  • Can I find deals for business class flights from Chicago to Aspen?

    Yes. Cheapflights offers flight deals from Chicago to Aspen by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago to Aspen?

    Currently, February is the cheapest month in which you can book a flight from Chicago to Aspen (average of $128). Flying from Chicago to Aspen in April is currently the most expensive (average of $344). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Aspen?

Book flights to Aspen if you plan to visit one of these locations
Snowmass Village
Buena Vista
Snowmass

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Top 2 airlines flying from Chicago to Aspen

Discover the top 2 airlines that operate flights from Chicago to Aspen. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated December 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$239Average$453FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$299Average$521FlexibilityNo cancel feeOn-time69%

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