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$285+ 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 2/10. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — ASE
Jan 25 — Feb 11
Sat 1/25
Sat 2/1
1 adult, Economy
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The best prices from Chicago to Aspen Pitkin County are usually found in May or January, booked 40 days in advance, depart on a Tuesday or Saturday and return on a Monday

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 January 20, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$329
(United Airlines)

One-way from

$285
(American Airlines)

Popular in

November

Cheapest in

May

Average price

$449
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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High demand for flights, 15% potential price rise
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Best time to find cheap flights, 5% potential price drop
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Average for round-trip flights in January 2025
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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 January 20, 2025.

This United Airlines deal was found by Cheapflights users on 1/19. 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.
Tue 3/43:35 pmORD - ASE
Nonstop3h 18mUnited Airlines
Tue 3/114:30 pmASE - ORD
Nonstop2h 55mUnited Airlines
Deal found 1/19$329
This American Airlines deal was found by Cheapflights users on 1/19. 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.
Wed 3/56:00 amORD - ASE
1 stop6h 36mAmerican Airlines
Wed 3/1211:35 amASE - ORD
Nonstop2h 58mAmerican Airlines
Deal found 1/19$339
This Delta deal was found by Cheapflights users on 1/20. 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.
Mon 2/106:00 amMDW - ASE
1 stop6h 53mDelta
Wed 2/123:00 pmASE - MDW
1 stop6h 20mDelta
Deal found 1/20$589
This Delta deal was found by Cheapflights users on 1/20. 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.
Mon 2/105:45 amORD - ASE
1 stop9h 35mDelta
Thu 2/133:00 pmASE - ORD
1 stop7h 49mDelta
Deal found 1/20$589

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 January 20, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

ChicagoAspen

ORD - ASE

ORDASE

Chicago O'Hare Intl

Tue 3/4

3:35 pm-5:53 pm

Nonstop3h 18m

Aspen Pitkin County

Tue 3/11

4:30 pm-8:25 pm

Nonstop2h 55m

$329

ChicagoAspen

ORD - ASE

ORDASE

Chicago O'Hare Intl

Wed 3/5

6:00 am-11:36 am

1 stop6h 36m

Aspen Pitkin County

Wed 3/12

11:35 am-3:33 pm

Nonstop2h 58m

$339

ChicagoAspen

MDW - ASE

MDWASE

Chicago Midway

Wed 3/5

6:00 am-2:20 pm

1 stop9h 20m

Aspen Pitkin County

Wed 3/12

2:55 pm-10:23 pm

1 stop6h 28m

$584

ChicagoAspen

ORD - ASE

ORDASE

Chicago O'Hare Intl

Mon 2/10

5:45 am-2:20 pm

1 stop9h 35m

Aspen Pitkin County

Thu 2/13

3:00 pm-11:49 pm

1 stop7h 49m

$589

ChicagoAspen

ORD - ASE

ORDASE

Chicago O'Hare Intl

Mon 2/10

12:25 pm-2:42 pm

Nonstop3h 17m

$285

ChicagoAspen

MDW - ASE

MDWASE

Chicago Midway

Mon 2/10

6:00 am-11:53 am

1 stop6h 53m

$295

ChicagoAspen

ORD - ASE

ORDASE

Chicago O'Hare Intl

Mon 2/17

7:05 am-2:20 pm

1 stop8h 15m

$295

ChicagoAspen

ORD - ASE

ORDASE

Chicago O'Hare Intl

Mon 2/17

8:58 am-11:35 am

Nonstop3h 37m

$325

ChicagoAspen

ORD - ASE

ORDASE

Chicago O'Hare Intl

Mon 2/10

1:40 pm-9:32 pm

2 stops8h 52m

$409

ChicagoAspen

ORD - ASE

ORDASE

Chicago O'Hare Intl

Sat 2/22

10:06 am-1:10 pm

3 stops28h 04m

$626

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/20

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 January.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
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 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 January 17, 2025.

To ensure you get the cheapest price possible for a flight from Chicago to Aspen, you should look to book at least 40 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 $674). 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 January 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 19% 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 Saturday afternoons when fares are most often at their lowest. Thursday afternoons 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 January 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 (4 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 January 20, 2025.
Read reviews from past customers who have flown United Airlines and Delta 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
9,696 reviews

Boarding

8.2

Comfort

7.9

Entertainment

7.1

Food

7.1

Overall

8.0

Crew

8.5

Reviews

1 / 10

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
9,696 reviews
Alaska Airlines
8.0
Very good
9,696 reviews

Boarding

8.2

Comfort

7.9

Entertainment

7.1

Food

7.1

Overall

8.0

Crew

8.5

Reviews

1 / 10

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
8,521 reviews
Alaska Airlines
8.0
Very good
9,696 reviews

Boarding

8.2

Comfort

7.9

Entertainment

7.1

Food

7.1

Overall

8.0

Crew

8.5

Reviews

1 / 10

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
8,982 reviews
Alaska Airlines
8.0
Very good
9,696 reviews

Boarding

8.2

Comfort

7.9

Entertainment

7.1

Food

7.1

Overall

8.0

Crew

8.5

Reviews

1 / 10

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
9,696 reviews

Boarding

8.2

Comfort

7.9

Entertainment

7.1

Food

7.1

Overall

8.0

Crew

8.5

Reviews

1 / 10

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 United Airlines. Our recent data shows that you can find tickets from as low as $329 on this airline. Additional options worth looking into are American Airlines and Delta, starting at $394 and $589 round-trip. United Airlines is currently priced 39% below the average price you’ll pay for this route.

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

    $285 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 $295 and $325, 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: Lufthansa (50%), United Airlines (47%), SkyWest Airlines (39%).

  • What are the cheapest flights from Chicago to Aspen?

    While on average a flight from Chicago to Aspen is generally $680, our data shows the cheapest flight currently is $324. When looking at the most popular route, (Chicago O'Hare Intl - Aspen Pitkin County), you can expect to pay $329 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 $674). 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?

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Carbondale
Buena Vista
Snowmass Village
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 January 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$298Average$490FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$315Average$558FlexibilityNo cancel feeOn-time69%
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