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Aspen

$145+ 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 6/9. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — ASE
May 4 — May 111
Sun 5/4
Sun 5/11
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 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 April 29, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$259
(United Airlines)

One-way from

$145
(American Airlines)

Popular in

November

Cheapest in

January

Average price

$645

Good round-trip deal

$415 or less

Good one-way deal

$284 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. 13% potential increase in price ($87 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 April 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 April 29, 2025.

This United Airlines deal was found by Cheapflights users on 4/29. 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 6/245:02 amORD - ASE
1 stop4h 40mUnited Airlines
Tue 7/19:15 amASE - ORD
Nonstop2h 58mUnited Airlines
Deal found 4/29$249
This American Airlines deal was found by Cheapflights users on 4/28. 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 6/1110:51 amORD - ASE
Nonstop3h 13mAmerican Airlines
Wed 6/1812:08 pmASE - ORD
Nonstop2h 51mAmerican Airlines
Deal found 4/28$264
This Delta deal was found by Cheapflights users on 4/28. 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 6/28:40 amORD - ASE
2 stops11h 34mDelta
Tue 6/108:05 amASE - ORD
1 stop7h 54mDelta
Deal found 4/28$289
This Delta deal was found by Cheapflights users on 4/28. 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 6/29:20 amMDW - ASE
2 stops10h 54mDelta
Tue 6/108:05 amASE - MDW
2 stops9h 36mDelta
Deal found 4/28$294

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 April 29, 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 6/24

5:02 am-8:42 am

1 stop4h 40m

Aspen Pitkin County

Tue 7/1

9:15 am-1:13 pm

Nonstop2h 58m

$249

ChicagoAspen

ORD - ASE

ORDASE

Chicago O'Hare Intl

Wed 6/11

10:51 am-1:04 pm

Nonstop3h 13m

Aspen Pitkin County

Wed 6/18

12:08 pm-3:59 pm

Nonstop2h 51m

$264

ChicagoAspen

ORD - ASE

ORDASE

Chicago O'Hare Intl

Mon 6/2

8:40 am-7:14 pm

2 stops11h 34m

Aspen Pitkin County

Tue 6/10

8:05 am-4:59 pm

1 stop7h 54m

$289

ChicagoAspen

MDW - ASE

MDWASE

Chicago Midway

Mon 6/2

9:20 am-7:14 pm

2 stops10h 54m

Aspen Pitkin County

Tue 6/10

8:05 am-6:41 pm

2 stops9h 36m

$294

ChicagoAspen

ORD - ASE

ORDASE

Chicago O'Hare Intl

Mon 6/9

10:51 am-1:04 pm

Nonstop3h 13m

$145

ChicagoAspen

ORD - ASE

ORDASE

Chicago O'Hare Intl

Mon 6/30

5:00 am-8:42 am

1 stop4h 42m

$155

ChicagoAspen

ORD - ASE

ORDASE

Chicago O'Hare Intl

Mon 6/9

5:35 am-11:22 am

1 stop6h 47m

$246

ChicagoAspen

MDW - ASE

MDWASE

Chicago Midway

Thu 6/12

6:00 am-11:22 am

1 stop6h 22m

$470

ChicagoAspen

ORD - ASE

ORDASE

Chicago O'Hare Intl

Mon 6/30

5:05 pm-4:05 pm

3 stops24h 00m

$1,143

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/28

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 April.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*2 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 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 April 25, 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 $672). 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 April 29, 2025.

One of the essential ways to save on airfare from Chicago to Aspen is to remain as flexible as possible. Flights that are at noon tend to be the most expensive. A flight in the morning could potentially save you up to 18% 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.

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 April 29, 2025.
Alaska Airlines
8.0
Very good
9,961 reviews

Crew

8.5

Boarding

8.2

Comfort

7.9

Entertainment

7.1

Food

7.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Alaska Airlines
8.0
Very good
9,961 reviews
Alaska Airlines
8.0
Very good
9,961 reviews

Crew

8.5

Boarding

8.2

Comfort

7.9

Entertainment

7.1

Food

7.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Delta
8.0
Very good
7,929 reviews
Alaska Airlines
8.0
Very good
9,961 reviews

Crew

8.5

Boarding

8.2

Comfort

7.9

Entertainment

7.1

Food

7.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
United Airlines
7.4
Good
8,696 reviews
Alaska Airlines
8.0
Very good
9,961 reviews

Crew

8.5

Boarding

8.2

Comfort

7.9

Entertainment

7.1

Food

7.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
American Airlines
7.2
Good
10,000 reviews
Alaska Airlines
8.0
Very good
9,961 reviews

Crew

8.5

Boarding

8.2

Comfort

7.9

Entertainment

7.1

Food

7.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

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 0 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 $259 on this airline. Additional options worth looking into are American Airlines and Delta, starting at $264 and $289 round-trip. United Airlines is currently priced 53% below the average price you’ll pay for this route.

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

    $145 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 United Airlines and Delta, with prices starting from $155 and $246, 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 (60%), Lufthansa (52%), SkyWest Airlines (46%).

  • What are the cheapest flights from Chicago to Aspen?

    While on average a flight from Chicago to Aspen is generally $521, our data shows the cheapest flight currently is $239. When looking at the most popular route, (Chicago O'Hare Intl - Aspen Pitkin County), you can expect to pay $274 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 $672). 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 April 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$277Average$499FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$315Average$556FlexibilityNo cancel feeOn-time69%

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