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Aspen

$191+ Cheap flights from Chicago (CHI) to Aspen (ASE)

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 9/14. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — ASE
Jul 7 — Jul 141
Mon 7/7
Mon 7/14
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 July 2, 2025.

Round-trip from

$191
(American Airlines)

Popular in

November

Cheapest in

January

Average price

$521

Good round-trip deal

$355 or less

Good one-way deal

$233 or less
From Chicago (CHI) to Aspen Pitkin County
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Highest demand for flights based on searches. 14% potential increase in price ($92 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 July 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 July 2, 2025.

This American Airlines deal was found by Cheapflights users on 6/30. 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.
Sun 9/149:31 amORD - ASE
Nonstop3h 10mAmerican Airlines
Wed 9/1712:14 pmASE - ORD
Nonstop2h 58mAmerican Airlines
Deal found 6/30$191
This United Airlines deal was found by Cheapflights users on 7/2. 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.
Mon 9/155:00 amORD - ASE
1 stop5h 27mUnited Airlines
Fri 9/196:15 pmASE - ORD
1 stop4h 44mUnited Airlines
Deal found 7/2$211
This Delta deal was found by Cheapflights users on 7/2. 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.
Wed 9/105:45 amORD - ASE
1 stop6h 36mDelta
Sat 9/137:16 amASE - ORD
1 stop8h 15mDelta
Deal found 7/2$294
This Delta deal was found by Cheapflights users on 7/1. 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 8/226:04 amMDW - ASE
1 stop6h 17mDelta
Tue 8/267:16 amASE - MDW
2 stops10h 21mDelta
Deal found 7/1$774

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 July 2, 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

Sun 9/14

9:31 am-11:41 am

Nonstop3h 10m

Aspen Pitkin County

Wed 9/17

12:14 pm-4:12 pm

Nonstop2h 58m

$191

ChicagoAspen

ORD - ASE

ORDASE

Chicago O'Hare Intl

Mon 9/15

5:00 am-9:27 am

1 stop5h 27m

Aspen Pitkin County

Fri 9/19

6:15 pm-11:59 pm

1 stop4h 44m

$211

ChicagoAspen

ORD - ASE

ORDASE

Chicago O'Hare Intl

Wed 9/10

5:45 am-11:21 am

1 stop6h 36m

Aspen Pitkin County

Sat 9/13

7:16 am-4:31 pm

1 stop8h 15m

$294

ChicagoAspen

MDW - ASE

MDWASE

Chicago Midway

Fri 8/22

6:04 am-11:21 am

1 stop6h 17m

Aspen Pitkin County

Tue 8/26

7:16 am-6:37 pm

2 stops10h 21m

$774

ChicagoAspen

ORD - ASE

ORDASE

Chicago O'Hare Intl

Tue 7/29

10:54 am-1:05 pm

Nonstop3h 11m

$234

ChicagoAspen

MDW - ASE

MDWASE

Chicago Midway

Wed 7/30

6:00 am-11:21 am

1 stop6h 21m

$270

ChicagoAspen

ORD - ASE

ORDASE

Chicago O'Hare Intl

Thu 8/7

4:00 pm-8:42 am

2 stops17h 42m

$278

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/30

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 27, 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 $668). 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 July 2, 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 mornings 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.

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 July 2, 2025.
Read reviews from past customers who have flown Delta, 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.
Delta
8.0
Very good
7,983 reviews

Entertainment

7.9

Food

7.3

Boarding

8.2

Overall

8.0

Crew

8.5

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Delta
8.0
Very good
7,983 reviews
Delta
8.0
Very good
7,983 reviews

Entertainment

7.9

Food

7.3

Boarding

8.2

Overall

8.0

Crew

8.5

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
United Airlines
7.4
Good
8,861 reviews
Delta
8.0
Very good
7,983 reviews

Entertainment

7.9

Food

7.3

Boarding

8.2

Overall

8.0

Crew

8.5

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,983 reviews

Entertainment

7.9

Food

7.3

Boarding

8.2

Overall

8.0

Crew

8.5

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

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 American Airlines. Our recent data shows that you can find tickets from as low as $191 on this airline. Additional options worth looking into are United Airlines and Delta, starting at $249 and $294 round-trip. American Airlines is currently priced 65% below the average price you’ll pay for this route.

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

    $234 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 $278, 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%), SkyWest Airlines (69%), American Airlines (55%).

  • What are the cheapest flights from Chicago to Aspen?

    While on average a flight from Chicago to Aspen is generally $444, our data shows the cheapest flight currently is $233. When looking at the most popular route, (Chicago O'Hare Intl - Aspen Pitkin County), you can expect to pay $201 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 $668). 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 July 2, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$239Average$486FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$315Average$556FlexibilityNo cancel feeOn-time69%

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