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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 12/9. Fares are subject to change and may not be available on all flights or dates of travel.
ASE — CHI
déc. 12 — déc. 191
ven. 12/12
ven. 12/19
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 novembre 12, 2025.

This Delta deal was found by Cheapflights users on 11/10. 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.
mar. 11/181:05 pmASE - ORD
1 stop8h 25mDelta
mer. 11/195:23 amORD - ASE
1 stop6h 58mDelta
Deal found 11/10$365
This American Airlines deal was found by Cheapflights users on 11/12. 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.
ven. 12/57:33 amASE - ORD
1 stop6h 46mAmerican Airlines
dim. 12/75:18 amORD - ASE
1 stop7h 31mAmerican Airlines
Deal found 11/12$431
This United Airlines deal was found by Cheapflights users on 11/12. 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.
ven. 12/51:35 pmASE - ORD
1 stop6h 41mUnited Airlines
dim. 12/73:35 pmORD - ASE
Nonstop3h 14mUnited Airlines
Deal found 11/12$435
This United Airlines deal was found by Cheapflights users on 11/9. 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.
mar. 11/181:35 pmASE - ORD
1 stop6h 23mUnited Airlines
ven. 11/217:10 amORD - ASE
1 stop4h 26mUnited Airlines
Deal found 11/9$503
This United Airlines deal was found by Cheapflights users on 11/12. 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.
mer. 12/109:00 amASE - ORD
Nonstop3h 12mUnited Airlines
ven. 12/128:04 pmORD - ASE
2 stops13h 57mUnited Airlines
Deal found 11/12$504
This United Airlines deal was found by Cheapflights users on 11/10. 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.
mar. 11/185:12 pmASE - ORD
2 stops15h 14mUnited Airlines
mer. 11/191:00 pmORD - ASE
1 stop4h 31mUnited Airlines
Deal found 11/10$563
This Delta deal was found by Cheapflights users on 11/11. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jeu. 11/201:05 pmASE - ORD
1 stop7h 51mDelta
ven. 11/215:23 amORD - ASE
1 stop6h 58mDelta
Deal found 11/11$576

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 novembre 12, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
1 star

Round-trip from

$401
(United Airlines)

One-way from

$211
(United Airlines)

Popular in

March

Cheapest in

April

Good round-trip deal

$333 or less

Good one-way deal

$320 or less
Provider with most accurate pricing for Aspen Pitkin County-Chicago (CHI) flight deals.
Search Deals
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. 14% potential increase in price ($72 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($20 potential savings vs. average RT price).
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 novembre 12, 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

jeu. 3/26

5:26 pm-11:56 pm

1 stop5h 30m

Chicago O'Hare Intl

lun. 3/30

4:00 pm-6:15 pm

Nonstop3h 15m

$401

AspenChicago

ASE - ORD

ASEORD

Aspen Pitkin County

ven. 12/5

12:25 pm-7:35 pm

1 stop6h 10m

Chicago O'Hare Intl

dim. 12/7

11:55 am-7:38 pm

1 stop8h 43m

$431

AspenChicago

ASE - ORD

ASEORD

Aspen Pitkin County

mer. 12/10

9:00 am-1:12 pm

Nonstop3h 12m

Chicago O'Hare Intl

ven. 12/12

8:04 pm-9:01 am

2 stops13h 57m

$504

AspenChicago

ASE - MDW

ASEMDW

Aspen Pitkin County

jeu. 3/26

3:00 pm-9:56 am

1 stop17h 56m

Chicago Midway

lun. 3/30

6:00 am-2:19 pm

1 stop9h 19m

$776

AspenChicago

ASE - ORD

ASEORD

Aspen Pitkin County

mar. 2/10

12:54 pm-4:55 pm

Nonstop3h 01m

$211

AspenChicago

ASE - ORD

ASEORD

Aspen Pitkin County

jeu. 12/11

12:40 pm-4:39 pm

Nonstop2h 59m

$211

AspenChicago

ASE - ORD

ASEORD

Aspen Pitkin County

mer. 12/10

12:40 pm-4:39 pm

Nonstop2h 59m

$211

AspenChicago

ASE - ORD

ASEORD

Aspen Pitkin County

dim. 1/11

2:48 pm-6:55 pm

Nonstop3h 07m

$211

AspenChicago

ASE - ORD

ASEORD

Aspen Pitkin County

mar. 1/13

1:33 pm-11:57 pm

1 stop9h 24m

$221

AspenChicago

ASE - ORD

ASEORD

Aspen Pitkin County

lun. 12/22

1:20 pm-9:14 pm

1 stop6h 54m

$221

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/11

Showing 1-10 of 17 results
1
2
  • 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 novembre 12, 2025.

It’s optimal to fly from Aspen to Chicago in the evening. By choosing this option you can save up to 62% on the cost of your flight, compared to a flight at noon.

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 novembre 12, 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
9,016 reviews

Boarding

7.7

Crew

8.1

Comfort

7.3

Entertainment

7.1

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
9,016 reviews
United Airlines
7.4
Good
9,016 reviews

Boarding

7.7

Crew

8.1

Comfort

7.3

Entertainment

7.1

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
11,052 reviews
United Airlines
7.4
Good
9,016 reviews

Boarding

7.7

Crew

8.1

Comfort

7.3

Entertainment

7.1

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 0 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 $401, United Airlines can have you in Chicago from Aspen in 5h 30m. 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 60% cheaper than the other options available to this destination.

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

    $211 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 $211 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: American Airlines (86%), SkyWest Airlines (86%), United Airlines( 86%).

  • What are the cheapest flights from Aspen to Chicago?

    While on average a flight from Aspen to Chicago is generally $822, our data shows the cheapest flight currently is $210. When looking at the most popular route, (Aspen Pitkin County - Chicago O'Hare Intl), you can expect to pay $311 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
Lansing
Hammond
Porter
Benton Harbor
Merrillville

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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 novembre 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$172Average$404FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$289Average$409FlexibilityNo cancel feeOn-time69%

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