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$248+ 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 4/19. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — ASE
Feb 25 — Mar 41
Tue 2/25
Tue 3/4
1 adult, Economy
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The best prices from Chicago to Aspen Pitkin County are usually found in January or May, booked 33 days in advance, depart on a Tuesday or Saturday and return on a Thursday

Cheap 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 February 20, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$349
(American Airlines)

One-way from

$248
(American Airlines)

Popular in

November

Cheapest in

January

Average price

$562

Good round-trip deal

$523 or less

Good one-way deal

$449 or less
Provider with most accurate pricing for Chicago (CHI)-Aspen Pitkin County flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Aspen Pitkin County flights.
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From Chicago (CHI) to Aspen Pitkin County
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One-way flight from Chicago (CHI) to Aspen Pitkin County
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Highest demand for flights based on searches. 15% potential increase in price ($98 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease ($30 potential savings vs. average RT price).
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Average for round-trip flights in February 2025
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Price to beat on a round-trip flight from Chicago (CHI) to Aspen Pitkin County.
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Price to beat on a one-way flight from Chicago (CHI) to Aspen Pitkin County.
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Find 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 February 20, 2025.

This American Airlines deal was found by Cheapflights users on 2/19. 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.
Thu 3/279:41 amORD - ASE
Nonstop3h 17mAmerican Airlines
Mon 3/311:45 pmASE - ORD
Nonstop2h 58mAmerican Airlines
Deal found 2/19$329
This United Airlines deal was found by Cheapflights users on 2/19. 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 7/175:00 amORD - ASE
1 stop4h 42mUnited Airlines
Mon 7/216:15 pmASE - ORD
1 stop5h 05mUnited Airlines
Deal found 2/19$363
This Delta deal was found by Cheapflights users on 2/20. 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.
Fri 4/256:04 amMDW - ASE
1 stop6h 34mDelta
Sun 4/271:39 pmASE - MDW
1 stop7h 47mDelta
Deal found 2/20$414
This Delta deal was found by Cheapflights users on 2/20. 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.
Fri 4/255:30 amORD - ASE
1 stop7h 08mDelta
Sun 4/271:39 pmASE - ORD
1 stop6h 11mDelta
Deal found 2/20$414

Find flights from Chicago to Aspen within your budget

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 February 20, 2025.

Fly from

Chicago

Fly to

Aspen

Route

Depart

Return

Price

ChicagoAspen

ORD - ASE

ORDASE

Chicago O'Hare Intl

Thu 3/27

9:41 am-11:58 am

Nonstop3h 17m

Aspen Pitkin County

Mon 3/31

1:45 pm-5:43 pm

Nonstop2h 58m

$329

ChicagoAspen

ORD - ASE

ORDASE

Chicago O'Hare Intl

Wed 3/12

3:40 pm-5:58 pm

Nonstop3h 18m

Aspen Pitkin County

Wed 3/19

4:30 pm-8:25 pm

Nonstop2h 55m

$409

ChicagoAspen

MDW - ASE

MDWASE

Chicago Midway

Fri 4/25

6:04 am-11:38 am

1 stop6h 34m

Aspen Pitkin County

Sun 4/27

1:39 pm-10:26 pm

1 stop7h 47m

$414

ChicagoAspen

ORD - ASE

ORDASE

Chicago O'Hare Intl

Fri 4/25

5:30 am-11:38 am

1 stop7h 08m

Aspen Pitkin County

Sun 4/27

1:39 pm-8:50 pm

1 stop6h 11m

$414

ChicagoAspen

ORD - ASE

ORDASE

Chicago O'Hare Intl

Sat 4/19

8:44 pm-11:51 am

2 stops16h 07m

$248

ChicagoAspen

ORD - ASE

ORDASE

Chicago O'Hare Intl

Mon 4/21

8:15 pm-11:38 am

2 stops16h 23m

$270

ChicagoAspen

ORD - ASE

ORDASE

Chicago O'Hare Intl

Wed 4/16

8:45 am-8:01 pm

2 stops12h 16m

$298

ChicagoAspen

MDW - ASE

MDWASE

Chicago Midway

Sun 3/2

6:28 pm-2:20 pm

2 stops20h 52m

$663

ChicagoAspen

ORD - ASE

ORDASE

Chicago O'Hare Intl

Thu 3/13

4:55 pm-1:11 pm

3 stops21h 16m

$738

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/18

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 February.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice 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 FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-Aspen flight deals on Cheapflights vs. FlightHub >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 FlightHub the most. FlightHub 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.

Travel insights for flights from Chicago to Aspen

Get recent, data-driven insights about flights from Chicago to Aspen including ideal travel times, pricing trends, and more.

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 February 14, 2025.

To ensure you get the cheapest price possible for a flight from Chicago to Aspen, you should look to book at least 33 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, November is the cheapest month in which you can book a flight from Chicago to Aspen (average of $448). Flying from Chicago to Aspen in December is currently the most expensive (average of $673). 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 February 20, 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 afternoon tend to be the most expensive. A flight in the evening could potentially save you up to 20% 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 September 29, 2024.

Travelers seeking maximum savings on their Chicago to Aspen flight should consider departing on Tuesday evenings when fares are most often at their lowest. Wednesday 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 February 20, 2025.

The most flights from CHI to ASE are scheduled on a Monday (6 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (5 on average).

Rainfall in Aspen by month

Plan your trip to Aspen by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Aspen ranges from 1.0 - 1.8 inches per month. April is typically the wettest month, when rainfall can reach 1.8 in. January is typically the driest time to visit Aspen when rainfall is around 1.0 in.

Temperature in Aspen by month

Plan your trip to Aspen by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Aspen, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 64.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 19.4 F).

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 February 20, 2025.
Read reviews from past customers who have flown Alaska Airlines, Delta and United Airlines from Chicago to Aspen. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
9,692 reviews

Entertainment

7.1

Boarding

8.2

Food

7.1

Comfort

7.9

Overall

8.0

Crew

8.5

Reviews

1 / 20

10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

Alaska Airlines
8.0
Very good
9,692 reviews
Alaska Airlines
8.0
Very good
9,692 reviews

Entertainment

7.1

Boarding

8.2

Food

7.1

Comfort

7.9

Overall

8.0

Crew

8.5

Reviews

1 / 20

10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

Delta
8.0
Very good
8,220 reviews
Alaska Airlines
8.0
Very good
9,692 reviews

Entertainment

7.1

Boarding

8.2

Food

7.1

Comfort

7.9

Overall

8.0

Crew

8.5

Reviews

1 / 20

10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

United Airlines
7.4
Good
8,766 reviews
Alaska Airlines
8.0
Very good
9,692 reviews

Entertainment

7.1

Boarding

8.2

Food

7.1

Comfort

7.9

Overall

8.0

Crew

8.5

Reviews

1 / 20

10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

American Airlines
7.2
Good
10,000 reviews
Alaska Airlines
8.0
Very good
9,692 reviews

Entertainment

7.1

Boarding

8.2

Food

7.1

Comfort

7.9

Overall

8.0

Crew

8.5

Reviews

1 / 20

10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

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 5 inbound flights from Chicago per day.

  • 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 $349 on this airline. Additional options worth looking into are United Airlines and Delta, starting at $358 and $414 round-trip. American Airlines is currently priced 35% below the average price you’ll pay for this route.

  • What are the cheapest airlines to fly from Chicago to Aspen one-way?

    $248 is the cheapest one-way deal found within the past few days, from American Airlines. You may also be able to find cheap deals on Delta and United Airlines, with prices starting from $270 and $298, respectively.

  • 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: United Airlines (53%), Lufthansa (50%), SkyWest Airlines (36%).

  • What are the cheapest flights from Chicago to Aspen?

    While on average a flight from Chicago to Aspen is generally $621, our data shows the cheapest flight currently is $304. When looking at the most popular route, (Chicago O'Hare Intl - Aspen Pitkin County), you can expect to pay $363 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, November is the cheapest month in which you can book a flight from Chicago to Aspen (average of $448). Flying from Chicago to Aspen in December is currently the most expensive (average of $673). 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 Chicago?

Book flights to Chicago if you plan to visit one of these locations
Snowmass Village
Carbondale
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 February 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$311Average$502FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$315Average$563FlexibilityNo cancel feeOn-time69%
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