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$127+ 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 1/9. Fares are subject to change and may not be available on all flights or dates of travel.
ASE — CHI
Nov 15 — Nov 221
Sat 11/15
Sat 11/22
1 adult, Economy
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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 October 16, 2025.

This Delta deal was found by Cheapflights users on 10/16. 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.
Fri 10/317:21 amASE - MDW
1 stop7h 05mDelta
Sun 11/25:00 amMDW - ASE
1 stop6h 10mDelta
Deal found 10/16$339
This Delta deal was found by Cheapflights users on 10/16. 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.
Fri 10/317:21 amASE - ORD
1 stop8h 20mDelta
Sun 11/25:20 amORD - ASE
1 stop6h 50mDelta
Deal found 10/16$339
This American Airlines deal was found by Cheapflights users on 10/15. 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.
Wed 11/127:34 amASE - ORD
1 stop6h 50mAmerican Airlines
Sat 11/1511:46 amORD - ASE
1 stop8h 45mAmerican Airlines
Deal found 10/15$350
This United Airlines deal was found by Cheapflights users on 10/16. 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.
Wed 11/121:35 pmASE - ORD
1 stop5h 05mUnited Airlines
Sun 11/167:10 amORD - ASE
1 stop4h 26mUnited Airlines
Deal found 10/16$411
This American Airlines deal was found by Cheapflights users on 10/16. 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.
Fri 10/318:00 amASE - ORD
1 stop8h 17mAmerican Airlines
Sun 11/25:18 amORD - ASE
1 stop7h 24mAmerican Airlines
Deal found 10/16$415
This American Airlines deal was found by Cheapflights users on 10/16. 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.
Mon 11/1712:25 pmASE - ORD
1 stop7h 56mAmerican Airlines
Thu 11/205:18 amORD - ASE
1 stop7h 24mAmerican Airlines
Deal found 10/16$441
This United Airlines deal was found by Cheapflights users on 10/15. 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 11/125:12 pmASE - ORD
2 stops13h 29mUnited Airlines
Sat 11/158:47 amORD - ASE
1 stop6h 49mUnited Airlines
Deal found 10/15$452
This United Airlines deal was found by Cheapflights users on 10/15. 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.
Thu 11/135:12 pmASE - ORD
2 stops13h 29mUnited Airlines
Sat 11/151:55 pmORD - ASE
1 stop7h 13mUnited Airlines
Deal found 10/15$455
This United Airlines deal was found by Cheapflights users on 10/16. 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.
Fri 10/317:10 amASE - ORD
2 stops12h 00mUnited Airlines
Sun 11/27:10 amORD - ASE
1 stop6h 19mUnited Airlines
Deal found 10/16$474
This United Airlines deal was found by Cheapflights users on 10/16. 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.
Mon 11/173:34 pmASE - ORD
1 stop4h 24mUnited Airlines
Thu 11/208:59 amORD - ASE
2 stops6h 37mUnited Airlines
Deal found 10/16$638
This Delta deal was found by Cheapflights users on 10/14. 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.
Wed 10/297:21 amASE - MDW
1 stop7h 48mDelta
Sun 11/25:00 amMDW - ASE
1 stop6h 10mDelta
Deal found 10/14$884

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 October 16, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$339
(Delta)

One-way from

$127
(American Airlines)

Popular in

December

Cheapest in

April

Average price

$366

Good round-trip deal

$368 or less

Good one-way deal

$320 or less
Provider with most accurate pricing for Aspen Pitkin County-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Aspen Pitkin County-Chicago (CHI) flights.
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From Aspen Pitkin County to Chicago (CHI)
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One-way flight from Aspen Pitkin County to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 6% potential increase in price ($30 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($17 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
Search Deals
Price to beat on a round-trip flight from Aspen Pitkin County to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Aspen Pitkin County to Chicago (CHI).
Search Deals

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 October 16, 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 - MDW

ASEMDW

Aspen Pitkin County

Fri 10/31

7:21 am-3:26 pm

1 stop7h 05m

Chicago Midway

Sun 11/2

5:00 am-10:10 am

1 stop6h 10m

$339

AspenChicago

ASE - MDW

ASEMDW

Aspen Pitkin County

Fri 10/31

7:21 am-3:26 pm

1 stop7h 05m

Chicago Midway

Tue 11/4

6:00 am-11:10 am

1 stop6h 10m

$339

AspenChicago

ASE - ORD

ASEORD

Aspen Pitkin County

Fri 10/31

7:21 am-4:41 pm

1 stop8h 20m

Chicago O'Hare Intl

Tue 11/4

5:20 am-11:10 am

1 stop6h 50m

$339

AspenChicago

ASE - ORD

ASEORD

Aspen Pitkin County

Fri 10/31

7:21 am-4:41 pm

1 stop8h 20m

Chicago O'Hare Intl

Sun 11/2

5:20 am-11:10 am

1 stop6h 50m

$339

AspenChicago

ASE - ORD

ASEORD

Aspen Pitkin County

Wed 11/12

7:34 am-3:24 pm

1 stop6h 50m

Chicago O'Hare Intl

Sat 11/15

11:46 am-7:31 pm

1 stop8h 45m

$350

AspenChicago

ASE - ORD

ASEORD

Aspen Pitkin County

Thu 11/13

12:25 pm-7:42 pm

1 stop6h 17m

Chicago O'Hare Intl

Sat 11/15

5:18 am-11:44 am

1 stop7h 26m

$350

AspenChicago

ASE - ORD

ASEORD

Aspen Pitkin County

Wed 11/12

1:35 pm-7:40 pm

1 stop5h 05m

Chicago O'Hare Intl

Sun 11/16

7:10 am-10:36 am

1 stop4h 26m

$411

AspenChicago

ASE - ORD

ASEORD

Aspen Pitkin County

Fri 10/31

8:00 am-5:17 pm

1 stop8h 17m

Chicago O'Hare Intl

Sun 11/2

5:18 am-11:42 am

1 stop7h 24m

$415

AspenChicago

ASE - ORD

ASEORD

Aspen Pitkin County

Mon 11/17

12:25 pm-9:21 pm

1 stop7h 56m

Chicago O'Hare Intl

Thu 11/20

5:18 am-11:42 am

1 stop7h 24m

$441

AspenChicago

ASE - ORD

ASEORD

Aspen Pitkin County

Wed 11/12

5:12 pm-7:41 am

2 stops13h 29m

Chicago O'Hare Intl

Sat 11/15

8:47 am-2:36 pm

1 stop6h 49m

$452

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/16

Showing 1-10 of 26 results
1
2
3
  • Most accurate provider: When it comes to deals on Aspen-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Aspen-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Aspen-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Aspen-Chicago flights, Cheapflights users trust FlightHub the most. FlightHub 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 Aspen-Chicago 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 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 $183). Flying from Aspen to Chicago in April is currently the most expensive (average of $361). 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 October 16, 2025.

It’s optimal to fly from Aspen to Chicago in the evening. By choosing this option you can save up to 55% 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 October 16, 2025.

The most flights from ASE to CHI 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).

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 October 16, 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
8,982 reviews

Comfort

7.3

Crew

8.1

Entertainment

7.1

Boarding

7.7

Food

6.6

Overall

7.4

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
United Airlines
7.4
Good
8,982 reviews
United Airlines
7.4
Good
8,982 reviews

Comfort

7.3

Crew

8.1

Entertainment

7.1

Boarding

7.7

Food

6.6

Overall

7.4

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
American Airlines
7.2
Good
11,043 reviews
United Airlines
7.4
Good
8,982 reviews

Comfort

7.3

Crew

8.1

Entertainment

7.1

Boarding

7.7

Food

6.6

Overall

7.4

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.

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 4 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 $411, Delta can have you in Chicago from Aspen in 5h 05m. 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 61% cheaper than the other options available to this destination.

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

    $127 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 $167 and $221, respectively.

  • 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 (80%), Lufthansa (79%), SkyWest Airlines( 71%).

  • What are the cheapest flights from Aspen to Chicago?

    While on average a flight from Aspen to Chicago is generally $782, our data shows the cheapest flight currently is $160. When looking at the most popular route, (Aspen Pitkin County - Chicago O'Hare Intl), you can expect to pay $452 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 $183). Flying from Aspen to Chicago in April is currently the most expensive (average of $361). 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
Porter
Benton Harbor
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 October 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$172Average$404FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$289Average$409FlexibilityNo cancel feeOn-time69%

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