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$211+ Cheap flights from Aspen (ASE) to Chicago (CHI)

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 10/14. Fares are subject to change and may not be available on all flights or dates of travel.
ASE — CHI
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
1 adult, Economy
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Cheap flight deals from Aspen to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Aspen (ASE) to Chicago (CHI). 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 15, 2025.

Round-trip from

$264
(American Airlines)

One-way from

$211
(American Airlines)

Popular in

March

Cheapest in

April

Average price

$368

Good round-trip deal

$343 or less

Good one-way deal

$272 or less
From Aspen Pitkin County to Chicago (CHI)
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One-way flight from Aspen Pitkin County to Chicago (CHI)
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Highest demand for flights based on searches. 9% potential increase in price ($47 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($15 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 Aspen Pitkin County to Chicago (CHI).
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Price to beat on a one-way flight from Aspen Pitkin County to Chicago (CHI).
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Find flight deals from Aspen to Chicago

Cheapest flights from Aspen to Chicago
Explore the most affordable flight options available from Aspen to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 15, 2025.

This American Airlines deal was found by Cheapflights users on 9/14. 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.
Fri 10/312:14 pmASE - ORD
Nonstop2h 58mAmerican Airlines
Sun 10/59:31 amORD - ASE
Nonstop3h 10mAmerican Airlines
Deal found 9/14$264
This Delta deal was found by Cheapflights users on 9/13. 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.
Sat 10/257:21 amASE - ORD
1 stop6h 37mDelta
Wed 10/295:20 amORD - ASE
1 stop6h 50mDelta
Deal found 9/13$269
This United Airlines deal was found by Cheapflights users on 9/13. 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.
Fri 12/58:30 amASE - ORD
1 stop7h 28mUnited Airlines
Sun 12/79:20 amORD - ASE
Nonstop3h 18mUnited Airlines
Deal found 9/13$296
This Delta deal was found by Cheapflights users on 9/13. 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 11/57:21 amASE - ORD
1 stop6h 44mDelta
Mon 11/105:32 amORD - ASE
1 stop6h 49mDelta
Deal found 9/13$314
This American Airlines deal was found by Cheapflights users on 9/14. 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.
Fri 9/2612:14 pmASE - ORD
Nonstop2h 58mAmerican Airlines
Sun 9/289:31 amORD - ASE
Nonstop3h 10mAmerican Airlines
Deal found 9/14$324
This United Airlines deal was found by Cheapflights users on 9/13. 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 10/69:00 amASE - ORD
Nonstop3h 03mUnited Airlines
Sun 10/128:49 amORD - ASE
1 stop5h 10mUnited Airlines
Deal found 9/13$325
This United Airlines deal was found by Cheapflights users on 9/13. 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 12/312:40 pmASE - ORD
Nonstop2h 59mUnited Airlines
Sun 12/73:35 pmORD - ASE
Nonstop3h 14mUnited Airlines
Deal found 9/13$329
This Delta deal was found by Cheapflights users on 9/13. 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 10/67:21 amASE - MDW
1 stop7h 48mDelta
Sun 10/126:00 amMDW - ASE
1 stop6h 10mDelta
Deal found 9/13$844
This Delta deal was found by Cheapflights users on 9/14. 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 10/37:16 amASE - MDW
2 stops10h 19mDelta
Sun 10/56:00 amMDW - ASE
1 stop6h 13mDelta
Deal found 9/14$849
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.
Fri 9/197:16 amASE - MDW
2 stops10h 19mDelta
Mon 9/226:00 amMDW - ASE
1 stop6h 13mDelta
Deal found 9/15$1,440

Cheapflights Fare Finder

 
Customize your flight search to find flights from Aspen to Chicago 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 15, 2025.
Use the filters below to find and compare flights from Aspen to Chicago that are best for you.

Fly from

Aspen

Fly to

Chicago

Route

Depart

Return

Price

AspenChicago

ASE - ORD

ASEORD

Aspen Pitkin County

Sat 10/25

7:21 am-2:58 pm

1 stop6h 37m

Chicago O'Hare Intl

Thu 10/30

5:20 am-11:10 am

1 stop6h 50m

$269

AspenChicago

ASE - ORD

ASEORD

Aspen Pitkin County

Fri 11/14

12:25 pm-7:40 pm

1 stop6h 15m

Chicago O'Hare Intl

Sun 11/16

5:18 am-11:42 am

1 stop7h 24m

$269

AspenChicago

ASE - ORD

ASEORD

Aspen Pitkin County

Wed 11/12

1:05 pm-9:53 pm

1 stop7h 48m

Chicago O'Hare Intl

Mon 11/17

5:32 am-11:21 am

1 stop6h 49m

$269

AspenChicago

ASE - ORD

ASEORD

Aspen Pitkin County

Tue 11/11

1:05 pm-9:53 pm

1 stop7h 48m

Chicago O'Hare Intl

Sat 11/15

5:32 am-11:21 am

1 stop6h 49m

$269

AspenChicago

ASE - ORD

ASEORD

Aspen Pitkin County

Fri 11/7

7:21 am-4:41 pm

1 stop8h 20m

Chicago O'Hare Intl

Thu 11/13

5:32 am-11:21 am

1 stop6h 49m

$269

AspenChicago

ASE - ORD

ASEORD

Aspen Pitkin County

Sat 11/8

7:21 am-2:58 pm

1 stop6h 37m

Chicago O'Hare Intl

Thu 11/13

5:32 am-11:21 am

1 stop6h 49m

$269

AspenChicago

ASE - ORD

ASEORD

Aspen Pitkin County

Fri 10/3

12:14 pm-4:12 pm

Nonstop2h 58m

Chicago O'Hare Intl

Sun 10/5

9:31 am-11:41 am

Nonstop3h 10m

$279

AspenChicago

ASE - ORD

ASEORD

Aspen Pitkin County

Tue 10/21

7:21 am-2:55 pm

1 stop6h 34m

Chicago O'Hare Intl

Sat 10/25

5:20 am-11:10 am

1 stop6h 50m

$314

AspenChicago

ASE - ORD

ASEORD

Aspen Pitkin County

Tue 11/18

1:05 pm-9:53 pm

1 stop7h 48m

Chicago O'Hare Intl

Mon 11/24

5:32 am-11:21 am

1 stop6h 49m

$314

AspenChicago

ASE - ORD

ASEORD

Aspen Pitkin County

Wed 11/5

7:21 am-3:05 pm

1 stop6h 44m

Chicago O'Hare Intl

Sat 11/8

5:20 am-11:10 am

1 stop6h 50m

$314

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/15

Showing 1-10 of 24 results
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2
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Best time to book a flight from Aspen to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Aspen 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 Aspen to Chicago

What is the cheapest month to book a flight from Aspen to Chicago?

Currently, August is the cheapest month in which you can book a flight from Aspen to Chicago (average of $245). Flying from Aspen to Chicago in March is currently the most expensive (average of $321). 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 ASE to CHI?

Find hourly flight availability from Aspen to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 15, 2025.

It’s optimal to fly from Aspen to Chicago in the afternoon. By choosing this option you can save up to 16% on the cost of your flight, compared to a flight at noon.

Weekly flight availability from Aspen to Chicago

Explore weekly flight availability from Aspen to Chicago. 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 15, 2025.

The most flights from ASE to CHI are scheduled on a Monday (5 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (5 on average).

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

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated September 15, 2025.
Read through reviews of airlines operating flights from Aspen to Chicago, such as United Airlines and American Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
8,929 reviews

Crew

8.1

Comfort

7.3

Overall

7.4

Entertainment

7.1

Boarding

7.7

Food

6.6

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!
United Airlines
7.4
Good
8,929 reviews
United Airlines
7.4
Good
8,929 reviews

Crew

8.1

Comfort

7.3

Overall

7.4

Entertainment

7.1

Boarding

7.7

Food

6.6

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!
American Airlines
7.2
Good
10,000 reviews
United Airlines
7.4
Good
8,929 reviews

Crew

8.1

Comfort

7.3

Overall

7.4

Entertainment

7.1

Boarding

7.7

Food

6.6

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!

Related info for your journey

Find useful and relevant information for your journey from Aspen to Chicago. 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 from for flights from Aspen to Chicago?

    Most people fly from Aspen Pitkin County (ASE) if they book a flight from Aspen to Chicago. On average, Pitkin County has 5 outbound flights to Chicago per day from 2 airlines. Aspen Pitkin County is conveniently located just 3.5 mi from Aspen’s city center.

  • How long is the flight from Aspen to Chicago?

    For as low as $269, Delta can have you in Chicago from Aspen in 6h 15m. Aspen and Chicago are separated by a distance of 1010 mi. This flight may include one or multiple stops.

  • What are the cheapest airlines flying from Aspen to Chicago round-trip?

    According to our current data, American Airlines ($172), and United Airlines ($289) offers the cheapest pricing from Aspen to Chicago. Users have found that American Airlines is 62% cheaper than the other options available to this destination.

  • What are the most reliable airlines from Aspen to Chicago?

    Before booking your flight to Chicago from Aspen, check out the most reliable airlines to get you to your destination on time: United Airlines (62%), SkyWest Airlines (57%), Lufthansa( 53%).

  • What are the cheapest flights from Aspen to Chicago?

    While on average a flight from Aspen to Chicago is generally $784, our data shows the cheapest flight currently is $223. When looking at the most popular route, (Aspen Pitkin County - Chicago O'Hare Intl), you can expect to pay $249 for that flight.

  • Can I find deals for flights from Aspen to Chicago that include hotel bookings?

    Yes. In addition to deals on Aspen to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Aspen to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Aspen to Chicago.

  • Can I find deals for business class flights from Aspen to Chicago?

    Yes. Cheapflights offers flight deals from Aspen to Chicago 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 Aspen to Chicago?

    Currently, August is the cheapest month in which you can book a flight from Aspen to Chicago (average of $245). Flying from Aspen to Chicago in March is currently the most expensive (average of $321). 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
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

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Alternative routes for Aspen to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
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Top 2 airlines flying from Aspen to Chicago

Discover the top 2 airlines that operate flights from Aspen to Chicago. 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 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$172Average$439FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$289Average$471FlexibilityNo cancel feeOn-time69%

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