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Aspen

$141+ 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 10/12. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — ASE
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Aspen Pitkin County are usually found in January or May, booked 30 days in advance, depart on a Tuesday or Sunday 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 June 12, 2025.

Round-trip from

$249
(United Airlines)

One-way from

$151
(American Airlines)

Popular in

November

Cheapest in

January

Average price

$496

Good round-trip deal

$420 or less

Good one-way deal

$195 or less
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. 14% potential increase in price ($89 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 June 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 June 12, 2025.

This United Airlines deal was found by Cheapflights users on 6/10. 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 7/225:00 amORD - ASE
1 stop4h 42mUnited Airlines
Tue 7/296:15 pmASE - ORD
1 stop5h 15mUnited Airlines
Deal found 6/10$249
This American Airlines deal was found by Cheapflights users on 6/11. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/189:40 amORD - ASE
Nonstop3h 06mAmerican Airlines
Wed 8/2012:03 pmASE - ORD
Nonstop2h 58mAmerican Airlines
Deal found 6/11$317
This Delta deal was found by Cheapflights users on 6/10. 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.
Sun 7/65:35 amORD - ASE
1 stop6h 47mDelta
Thu 7/108:05 amASE - ORD
2 stops11h 19mDelta
Deal found 6/10$604
This Delta deal was found by Cheapflights users on 6/10. 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 8/286:00 amMDW - ASE
1 stop6h 21mDelta
Sat 8/307:16 amASE - MDW
1 stop7h 12mDelta
Deal found 6/10$709

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 June 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 7/22

5:00 am-8:42 am

1 stop4h 42m

Aspen Pitkin County

Tue 7/29

6:15 pm-12:30 am

1 stop5h 15m

$249

ChicagoAspen

ORD - ASE

ORDASE

Chicago O'Hare Intl

Mon 8/18

9:40 am-11:46 am

Nonstop3h 06m

Aspen Pitkin County

Wed 8/20

12:03 pm-4:01 pm

Nonstop2h 58m

$317

ChicagoAspen

ORD - ASE

ORDASE

Chicago O'Hare Intl

Sun 7/6

5:35 am-11:22 am

1 stop6h 47m

Aspen Pitkin County

Thu 7/10

8:05 am-8:24 pm

2 stops11h 19m

$604

ChicagoAspen

MDW - ASE

MDWASE

Chicago Midway

Thu 8/28

6:00 am-11:21 am

1 stop6h 21m

Aspen Pitkin County

Sat 8/30

7:16 am-3:28 pm

1 stop7h 12m

$709

ChicagoAspen

ORD - ASE

ORDASE

Chicago O'Hare Intl

Sun 10/12

6:00 am-11:39 am

1 stop6h 39m

$141

ChicagoAspen

ORD - ASE

ORDASE

Chicago O'Hare Intl

Tue 7/29

1:23 pm-6:04 pm

1 stop5h 41m

$151

ChicagoAspen

ORD - ASE

ORDASE

Chicago O'Hare Intl

Tue 7/29

7:35 pm-9:44 pm

Nonstop3h 09m

$181

ChicagoAspen

MDW - ASE

MDWASE

Chicago Midway

Tue 7/29

6:00 am-11:21 am

1 stop6h 21m

$230

ChicagoAspen

ORD - ASE

ORDASE

Chicago O'Hare Intl

Fri 8/1

5:00 pm-4:02 pm

3 stops24h 02m

$466

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/9

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 June 9, 2025.

To ensure you get the cheapest price possible for a flight from Chicago to Aspen, you should look to book at least 30 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 $670). 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 June 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 at noon tend to be the most expensive. A flight in the morning could potentially save you up to 16% 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 June 12, 2025.

The most flights from CHI to ASE are scheduled on a Monday (3 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (2 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 June 12, 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
10,000 reviews

Boarding

8.1

Food

7.1

Crew

8.5

Comfort

7.8

Overall

8.0

Entertainment

7.1

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
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Food

7.1

Crew

8.5

Comfort

7.8

Overall

8.0

Entertainment

7.1

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
7,950 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Food

7.1

Crew

8.5

Comfort

7.8

Overall

8.0

Entertainment

7.1

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
8,790 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Food

7.1

Crew

8.5

Comfort

7.8

Overall

8.0

Entertainment

7.1

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
10,000 reviews

Boarding

8.1

Food

7.1

Crew

8.5

Comfort

7.8

Overall

8.0

Entertainment

7.1

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 2 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 $249 on this airline. Additional options worth looking into are American Airlines and Delta, starting at $290 and $604 round-trip. United Airlines is currently priced 54% below the average price you’ll pay for this route.

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

    $151 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 $181 and $230, 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 (74%), Lufthansa (65%), SkyWest Airlines (53%).

  • What are the cheapest flights from Chicago to Aspen?

    While on average a flight from Chicago to Aspen is generally $377, our data shows the cheapest flight currently is $140. When looking at the most popular route, (Chicago O'Hare Intl - Aspen Pitkin County), you can expect to pay $249 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 $670). 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 June 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$277Average$481FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$315Average$554FlexibilityNo cancel feeOn-time69%

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