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$191+ 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 2/27. Fares are subject to change and may not be available on all flights or dates of travel.
ASE — CHI
Mar 13 — Mar 201
Fri 3/13
Fri 3/20
1 adult, Economy
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Cheap 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 February 11, 2026.

This American Airlines deal was found by Cheapflights users on 2/11. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/113:46 pm
ASE
-
ORD
Nonstop3h 01m
American Airlines
Mon 3/1610:18 am
ORD
-
ASE
Nonstop3h 31m
American Airlines
Deal found 2/11$331
This American Airlines deal was found by Cheapflights users on 2/8. 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.
Thu 2/2611:51 am
ASE
-
ORD
Nonstop2h 58m
American Airlines
Sun 3/17:10 am
ORD
-
ASE
Nonstop3h 22m
American Airlines
Deal found 2/8$333
This United Airlines deal was found by Cheapflights users on 2/11. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/276:25 pm
ASE
-
ORD
1 stop5h 19m
United Airlines
Tue 6/27:00 am
ORD
-
ASE
1 stop4h 36m
United Airlines
Deal found 2/11$351
This United Airlines deal was found by Cheapflights users on 2/9. 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.
Wed 3/114:20 pm
ASE
-
ORD
Nonstop3h 00m
United Airlines
Wed 3/189:00 am
ORD
-
ASE
Nonstop3h 41m
United Airlines
Deal found 2/9$360
This Delta deal was found by Cheapflights users on 2/11. 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.
Wed 5/278:05 am
ASE
-
ORD
2 stops11h 14m
Delta
Tue 6/26:00 am
ORD
-
ASE
1 stop6h 19m
Delta
Deal found 2/11$366
This United Airlines deal was found by Cheapflights users on 2/7. 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 6/109:05 am
ASE
-
ORD
Nonstop3h 08m
United Airlines
Sun 6/147:40 pm
ORD
-
ASE
Nonstop3h 06m
United Airlines
Deal found 2/7$375
This United Airlines deal was found by Cheapflights users on 2/9. 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.
Fri 7/106:25 pm
ASE
-
ORD
1 stop5h 19m
United Airlines
Sun 7/127:40 pm
ORD
-
ASE
Nonstop3h 06m
United Airlines
Deal found 2/9$386
This Delta deal was found by Cheapflights users on 2/9. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/83:00 pm
ASE
-
MDW
1 stop6h 31m
Delta
Wed 4/156:00 am
MDW
-
ASE
1 stop6h 38m
Delta
Deal found 2/9$554
This Delta deal was found by Cheapflights users on 2/9. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/111:45 pm
ASE
-
MDW
1 stop7h 46m
Delta
Wed 3/186:00 am
MDW
-
ASE
1 stop6h 40m
Delta
Deal found 2/9$784
This Delta deal was found by Cheapflights users on 2/9. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/111:45 pm
ASE
-
MDW
1 stop7h 46m
Delta
Mon 3/166:00 am
MDW
-
ASE
1 stop6h 40m
Delta
Deal found 2/9$900
This Delta deal was found by Cheapflights users on 2/10. 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.
Thu 7/168:05 am
ASE
-
MDW
1 stop7h 20m
Delta
Sun 7/196:00 am
MDW
-
ASE
1 stop6h 29m
Delta
Deal found 2/10$1,169
This Delta deal was found by Cheapflights users on 2/9. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/108:05 am
ASE
-
MDW
1 stop7h 20m
Delta
Sun 7/126:00 am
MDW
-
ASE
1 stop6h 29m
Delta
Deal found 2/9$1,269

Find 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 February 11, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$331
(American Airlines)

One-way from

$191
(American Airlines)

Popular in

December

Cheapest in

April

Average price

$550

Good round-trip deal

$289 or less

Good one-way deal

$346 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.
Search Deals
From Aspen Pitkin County to Chicago (CHI)
Search Deals
One-way flight from Aspen Pitkin County to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 27% potential increase in price ($175 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($24 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2026
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 February 11, 2026.
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

Wed 3/11

3:46 pm-7:47 pm

Nonstop3h 01m

Chicago O'Hare Intl

Mon 3/16

7:15 am-9:37 am

Nonstop3h 22m

$331

AspenChicago

ASE - ORD

ASEORD

Aspen Pitkin County

Wed 5/27

12:25 pm-4:33 pm

Nonstop3h 08m

Chicago O'Hare Intl

Tue 6/2

7:40 pm-9:46 pm

Nonstop3h 06m

$331

AspenChicago

ASE - ORD

ASEORD

Aspen Pitkin County

Thu 2/26

11:51 am-3:49 pm

Nonstop2h 58m

Chicago O'Hare Intl

Sun 3/1

7:10 am-9:32 am

Nonstop3h 22m

$333

AspenChicago

ASE - ORD

ASEORD

Aspen Pitkin County

Wed 6/10

9:05 am-1:13 pm

Nonstop3h 08m

Chicago O'Hare Intl

Sun 6/14

5:00 am-10:36 am

1 stop6h 36m

$341

AspenChicago

ASE - ORD

ASEORD

Aspen Pitkin County

Fri 7/10

5:25 pm-12:44 am

1 stop6h 19m

Chicago O'Hare Intl

Sun 7/12

5:00 am-8:43 am

1 stop4h 43m

$351

AspenChicago

ASE - MDW

ASEMDW

Aspen Pitkin County

Wed 4/8

3:00 pm-10:31 pm

1 stop6h 31m

Chicago Midway

Wed 4/15

6:00 am-11:38 am

1 stop6h 38m

$554

AspenChicago

ASE - MDW

ASEMDW

Aspen Pitkin County

Wed 3/11

1:45 pm-10:31 pm

1 stop7h 46m

Chicago Midway

Wed 3/18

6:00 am-11:40 am

1 stop6h 40m

$784

AspenChicago

ASE - MDW

ASEMDW

Aspen Pitkin County

Wed 3/11

1:45 pm-10:31 pm

1 stop7h 46m

Chicago Midway

Mon 3/16

6:00 am-11:40 am

1 stop6h 40m

$900

AspenChicago

ASE - MDW

ASEMDW

Aspen Pitkin County

Thu 7/16

8:05 am-4:25 pm

1 stop7h 20m

Chicago Midway

Sun 7/19

6:00 am-11:29 am

1 stop6h 29m

$1,169

AspenChicago

ASE - MDW

ASEMDW

Aspen Pitkin County

Fri 7/10

8:05 am-4:25 pm

1 stop7h 20m

Chicago Midway

Sun 7/12

6:00 am-11:29 am

1 stop6h 29m

$1,269

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/11

Showing 1-10 of 29 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 January is currently the most expensive (average of $376). 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 February 11, 2026.

When flying from Aspen to Chicago, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

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 February 11, 2026.
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
9,276 reviews

Entertainment

7.1

Crew

8.1

Boarding

7.7

Food

6.6

Overall

7.4

Comfort

7.3

Reviews

1 / 20
10.0
Excellent

Michelle,Dec 2025

DEN - MKE

I liked that the plane waited 5 minutes for a family whose incoming plane was late. This was the last flight of the day to MKE. Flight attendants actually checked in throughout the flight. Although, not really friendly. Happy to see screens on seat backs again. This is my first time not flying first class in over 10 years. It was economy plus.
United Airlines
7.4
Good
9,276 reviews
United Airlines
7.4
Good
9,276 reviews

Entertainment

7.1

Crew

8.1

Boarding

7.7

Food

6.6

Overall

7.4

Comfort

7.3

Reviews

1 / 20
10.0
Excellent

Michelle,Dec 2025

DEN - MKE

I liked that the plane waited 5 minutes for a family whose incoming plane was late. This was the last flight of the day to MKE. Flight attendants actually checked in throughout the flight. Although, not really friendly. Happy to see screens on seat backs again. This is my first time not flying first class in over 10 years. It was economy plus.
American Airlines
7.2
Good
11,267 reviews
United Airlines
7.4
Good
9,276 reviews

Entertainment

7.1

Crew

8.1

Boarding

7.7

Food

6.6

Overall

7.4

Comfort

7.3

Reviews

1 / 20
10.0
Excellent

Michelle,Dec 2025

DEN - MKE

I liked that the plane waited 5 minutes for a family whose incoming plane was late. This was the last flight of the day to MKE. Flight attendants actually checked in throughout the flight. Although, not really friendly. Happy to see screens on seat backs again. This is my first time not flying first class in over 10 years. It was economy plus.

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 2 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 $331, American Airlines can have you in Chicago from Aspen in 3h 01m. 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 ($319) 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 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 (57%), Lufthansa (57%), SkyWest Airlines( 50%).

  • What are the cheapest flights from Aspen to Chicago?

    While on average a flight from Aspen to Chicago is generally $538, our data shows the cheapest flight currently is $249. When looking at the most popular route, (Aspen Pitkin County - Chicago O'Hare Intl), you can expect to pay $351 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 January is currently the most expensive (average of $376). 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
Merrillville
Hammond
Porter
Benton Harbor

Browse thousands of different options on Cheapflights for your next trip

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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 February 11, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$172Average$404FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$319Average$409FlexibilityNo cancel feeOn-time69%

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