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Aspen

$211+ 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 12/7. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — ASE
Oct 17 — Oct 241
Fri 10/17
Fri 10/24
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Aspen Pitkin County are usually found in September or May, booked 28 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 September 17, 2025.

Round-trip from

$191
(American Airlines)

Popular in

November

Cheapest in

September

Average price

$414

Good round-trip deal

$325 or less

Good one-way deal

$360 or less
From Chicago (CHI) to Aspen Pitkin County
Search Deals
Highest demand for flights based on searches. 16% potential increase in price ($114 potential increase over avg. RT price).
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Cheapest flight prices on average. 8% potential price decrease ($42 potential savings vs. average RT price).
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Average for round-trip flights in September 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 September 17, 2025.

This American Airlines deal was found by Cheapflights users on 9/16. 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 10/19:31 amORD - ASE
Nonstop3h 10mAmerican Airlines
Sat 10/412:14 pmASE - ORD
Nonstop2h 58mAmerican Airlines
Deal found 9/16$279
This Delta deal was found by Cheapflights users on 9/17. 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 11/205:32 amORD - ASE
1 stop6h 49mDelta
Sun 11/231:05 pmASE - ORD
1 stop7h 48mDelta
Deal found 9/17$284
This United Airlines deal was found by Cheapflights users on 9/15. 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.
Wed 10/17:10 amORD - ASE
1 stop4h 29mUnited Airlines
Sat 10/49:00 amASE - ORD
Nonstop3h 03mUnited Airlines
Deal found 9/15$289
This United Airlines deal was found by Cheapflights users on 9/16. 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.
Sat 10/119:20 amORD - ASE
Nonstop3h 06mUnited Airlines
Mon 10/139:00 amASE - ORD
Nonstop3h 03mUnited Airlines
Deal found 9/16$290
This American Airlines deal was found by Cheapflights users on 9/15. 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.
Tue 9/3010:03 amORD - ASE
1 stop7h 07mAmerican Airlines
Sat 10/44:49 pmASE - ORD
1 stop6h 10mAmerican Airlines
Deal found 9/15$299
This United Airlines deal was found by Cheapflights users on 9/15. 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 10/207:45 pmORD - ASE
Nonstop3h 10mUnited Airlines
Wed 10/2212:40 pmASE - ORD
Nonstop3h 03mUnited Airlines
Deal found 9/15$311
This United Airlines deal was found by Cheapflights users on 9/17. 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.
Wed 12/177:10 amORD - ASE
1 stop4h 28mUnited Airlines
Mon 12/2211:55 amASE - ORD
Nonstop3h 05mUnited Airlines
Deal found 9/17$313
This American Airlines deal was found by Cheapflights users on 9/17. 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.
Sat 9/279:31 amORD - ASE
Nonstop3h 10mAmerican Airlines
Thu 10/212:14 pmASE - ORD
Nonstop2h 58mAmerican Airlines
Deal found 9/17$324
This Delta deal was found by Cheapflights users on 9/16. 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 10/205:20 amORD - ASE
1 stop6h 50mDelta
Wed 10/227:21 amASE - ORD
1 stop6h 34mDelta
Deal found 9/16$331
This Delta deal was found by Cheapflights users on 9/15. 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 10/206:00 amMDW - ASE
1 stop6h 10mDelta
Wed 10/227:21 amASE - MDW
1 stop7h 48mDelta
Deal found 9/15$455
This Delta deal was found by Cheapflights users on 9/15. 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 10/126:00 amMDW - ASE
1 stop6h 10mDelta
Wed 10/157:21 amASE - MDW
1 stop7h 48mDelta
Deal found 9/15$525
This Delta deal was found by Cheapflights users on 9/16. 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 10/306:00 amMDW - ASE
1 stop6h 10mDelta
Sun 11/27:21 amASE - MDW
1 stop7h 48mDelta
Deal found 9/16$590

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 September 17, 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

Thu 11/20

5:32 am-11:21 am

1 stop6h 49m

Aspen Pitkin County

Sun 11/23

1:05 pm-9:53 pm

1 stop7h 48m

$284

ChicagoAspen

ORD - ASE

ORDASE

Chicago O'Hare Intl

Fri 2/27

7:10 am-9:51 am

Nonstop3h 41m

Aspen Pitkin County

Wed 3/4

12:11 pm-8:42 pm

1 stop7h 31m

$299

ChicagoAspen

ORD - ASE

ORDASE

Chicago O'Hare Intl

Sat 10/11

4:09 pm-9:39 pm

1 stop6h 30m

Aspen Pitkin County

Mon 10/13

9:00 am-1:03 pm

Nonstop3h 03m

$300

ChicagoAspen

ORD - ASE

ORDASE

Chicago O'Hare Intl

Sun 2/1

9:40 am-12:01 pm

Nonstop3h 21m

Aspen Pitkin County

Fri 2/6

1:00 pm-5:00 pm

Nonstop3h 00m

$311

ChicagoAspen

ORD - ASE

ORDASE

Chicago O'Hare Intl

Wed 12/17

7:10 am-10:38 am

1 stop4h 28m

Aspen Pitkin County

Mon 12/22

11:55 am-4:00 pm

Nonstop3h 05m

$313

ChicagoAspen

ORD - ASE

ORDASE

Chicago O'Hare Intl

Tue 1/6

5:00 am-12:01 pm

1 stop8h 01m

Aspen Pitkin County

Fri 1/9

8:08 am-5:38 pm

1 stop8h 30m

$331

ChicagoAspen

ORD - ASE

ORDASE

Chicago O'Hare Intl

Mon 9/29

1:00 pm-4:54 pm

1 stop4h 54m

Aspen Pitkin County

Mon 10/6

12:40 pm-4:43 pm

Nonstop3h 03m

$334

ChicagoAspen

ORD - ASE

ORDASE

Chicago O'Hare Intl

Thu 1/8

5:00 am-12:01 pm

1 stop8h 01m

Aspen Pitkin County

Sun 1/11

3:53 pm-7:50 pm

Nonstop2h 57m

$339

ChicagoAspen

ORD - ASE

ORDASE

Chicago O'Hare Intl

Thu 12/25

5:00 am-11:49 am

1 stop7h 49m

Aspen Pitkin County

Tue 12/30

12:56 pm-5:11 pm

Nonstop3h 15m

$339

ChicagoAspen

ORD - ASE

ORDASE

Chicago O'Hare Intl

Thu 11/20

7:10 am-10:36 am

1 stop4h 26m

Aspen Pitkin County

Wed 11/26

3:34 pm-11:59 pm

1 stop7h 25m

$349

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/16

Showing 1-10 of 27 results
1
2
3

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 September 12, 2025.

To ensure you get the cheapest price possible for a flight from Chicago to Aspen, you should look to book at least 28 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, September is the cheapest month in which you can book a flight from Chicago to Aspen (average of $447). Flying from Chicago to Aspen in December is currently the most expensive (average of $659). 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 September 17, 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 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 September 17, 2025.

The most flights from CHI to ASE are scheduled on a Monday (4 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (4 on average).

How much does it cost to fly round-trip from Chicago to Aspen?

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 September 17, 2025.
Read reviews from past customers who have flown 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.
United Airlines
7.4
Good
8,926 reviews

Entertainment

7.1

Comfort

7.3

Overall

7.4

Crew

8.1

Boarding

7.7

Food

6.6

Reviews

1 / 20
10.0
Excellent

Julia,Sep 2025

BUF - DEN

The staff were amazing, from check in to boarding and on the flight. The range of entertainment options were really good as well.
United Airlines
7.4
Good
8,926 reviews
United Airlines
7.4
Good
8,926 reviews

Entertainment

7.1

Comfort

7.3

Overall

7.4

Crew

8.1

Boarding

7.7

Food

6.6

Reviews

1 / 20
10.0
Excellent

Julia,Sep 2025

BUF - DEN

The staff were amazing, from check in to boarding and on the flight. The range of entertainment options were really good as well.
American Airlines
7.2
Good
10,000 reviews
United Airlines
7.4
Good
8,926 reviews

Entertainment

7.1

Comfort

7.3

Overall

7.4

Crew

8.1

Boarding

7.7

Food

6.6

Reviews

1 / 20
10.0
Excellent

Julia,Sep 2025

BUF - DEN

The staff were amazing, from check in to boarding and on the flight. The range of entertainment options were really good as well.

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 4 inbound flights from Chicago per day.

  • How long is the flight from Chicago to Aspen?

    There are many flights that can get you from Chicago to Aspen in 3h 41m. Fly via Delta, American Airlines, or United Airlines to get the fastest option. Chicago and Aspen are separated by a distance of 1010 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • 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 $239 on this airline. An additional option worth looking into is United Airlines, starting at $331. American Airlines is currently priced 57% below the average price you’ll pay for this route.

  • 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 (73%), American Airlines (69%), SkyWest Airlines (68%).

  • What are the cheapest flights from Chicago to Aspen?

    While on average a flight from Chicago to Aspen is generally $443, our data shows the cheapest flight currently is $167. When looking at the most popular route, (Chicago O'Hare Intl - Aspen Pitkin County), you can expect to pay $269 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, September is the cheapest month in which you can book a flight from Chicago to Aspen (average of $447). Flying from Chicago to Aspen in December is currently the most expensive (average of $659). 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 Aspen?

Book flights to Aspen if you plan to visit one of these locations
Snowmass Village
Carbondale
Buena Vista
Snowmass

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Alternative routes for Chicago to Aspen

See prices for flight routes from nearby airports that may be better suited for you.
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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 September 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$239Average$476FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$331Average$552FlexibilityNo cancel feeOn-time69%

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