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$177+ 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 9/4. Fares are subject to change and may not be available on all flights or dates of travel.
ASE — CHI
Sep 2 — Sep 91
Wed 9/2
Wed 9/9
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 August 3, 2026.

This American Airlines deal was found by Cheapflights users on 8/1. 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 9/177:00 am
ASE
-
ORD
Nonstop3h 05m
American Airlines
Sun 9/207:20 pm
ORD
-
ASE
Nonstop3h 09m
American Airlines
Deal found 8/1$353
This United Airlines deal was found by Cheapflights users on 8/1. 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 9/172:15 pm
ASE
-
ORD
1 stop6h 15m
United Airlines
Sun 9/209:00 am
ORD
-
ASE
Nonstop3h 10m
United Airlines
Deal found 8/1$363
This American Airlines deal was found by Cheapflights users on 7/30. 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 10/712:48 pm
ASE
-
ORD
Nonstop3h 17m
American Airlines
Sun 10/119:59 am
ORD
-
ASE
Nonstop3h 16m
American Airlines
Deal found 7/30$391
This United Airlines deal was found by Cheapflights users on 7/29. 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 11/51:30 pm
ASE
-
ORD
1 stop5h 35m
United Airlines
Sun 11/87:00 am
ORD
-
ASE
1 stop4h 46m
United Airlines
Deal found 7/29$393
This Delta deal was found by Cheapflights users on 7/29. 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 11/57:30 am
ASE
-
MDW
1 stop6h 47m
Delta
Sun 11/86:04 am
MDW
-
ASE
1 stop6h 20m
Delta
Deal found 7/29$403
This American Airlines deal was found by Cheapflights users on 7/30. 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 9/197:00 am
ASE
-
ORD
Nonstop3h 05m
American Airlines
Sun 9/207:20 pm
ORD
-
ASE
Nonstop3h 09m
American Airlines
Deal found 7/30$416
This United Airlines deal was found by Cheapflights users on 7/30. 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 9/193:20 pm
ASE
-
ORD
2 stops13h 35m
United Airlines
Sun 9/209:00 am
ORD
-
ASE
Nonstop3h 10m
United Airlines
Deal found 7/30$419
This American Airlines deal was found by Cheapflights users on 7/30. 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 8/201:54 pm
ASE
-
ORD
Nonstop3h 13m
American Airlines
Sun 8/2311:16 am
ORD
-
ASE
Nonstop3h 08m
American Airlines
Deal found 7/30$429
This Delta deal was found by Cheapflights users on 8/2. 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 9/37:20 am
ASE
-
MDW
1 stop7h 55m
Delta
Sun 9/66:05 am
MDW
-
ASE
1 stop6h 18m
Delta
Deal found 8/2$461
This Delta deal was found by Cheapflights users on 8/2. 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 9/47:20 am
ASE
-
MDW
1 stop7h 55m
Delta
Tue 9/86:05 am
MDW
-
ASE
1 stop6h 16m
Delta
Deal found 8/2$746
This Delta deal was found by Cheapflights users on 7/31. 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 8/197:20 am
ASE
-
MDW
1 stop7h 55m
Delta
Sun 8/236:05 am
MDW
-
ASE
1 stop6h 18m
Delta
Deal found 7/31$854
This Delta deal was found by Cheapflights users on 7/29. 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 9/127:35 am
ASE
-
MDW
1 stop6h 49m
Delta
Mon 9/146:05 am
MDW
-
ASE
1 stop6h 16m
Delta
Deal found 7/29$1,116

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 August 3, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$353
(American Airlines)

One-way from

$177
(American Airlines)

Good round-trip deal

$458 or less

Good one-way deal

$254 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
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 August 3, 2026.
Use the filters below to find and compare flights from Aspen to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

AspenChicago

ASE - MDW

ASEMDW

Aspen Pitkin County

Thu 11/5

7:30 am-3:17 pm

1 stop6h 47m

Chicago Midway

Sun 11/8

6:04 am-11:24 am

1 stop6h 20m

$403

AspenChicago

ASE - ORD

ASEORD

Aspen Pitkin County

Sat 9/19

3:20 pm-5:55 am

2 stops13h 35m

Chicago O'Hare Intl

Sun 9/20

9:00 am-11:10 am

Nonstop3h 10m

$419

AspenChicago

ASE - ORD

ASEORD

Aspen Pitkin County

Sat 9/19

12:53 pm-10:04 pm

1 stop8h 11m

Chicago O'Hare Intl

Sun 9/20

7:20 pm-9:29 pm

Nonstop3h 09m

$426

AspenChicago

ASE - MDW

ASEMDW

Aspen Pitkin County

Thu 9/3

7:20 am-4:15 pm

1 stop7h 55m

Chicago Midway

Sun 9/6

6:05 am-11:23 am

1 stop6h 18m

$461

AspenChicago

ASE - ORD

ASEORD

Aspen Pitkin County

Thu 9/3

4:45 pm-11:59 pm

1 stop6h 14m

Chicago O'Hare Intl

Sun 9/6

8:56 am-11:06 am

Nonstop3h 10m

$473
Quickest round-trip

AspenChicago

ASE - ORD

ASEORD

Aspen Pitkin County

Sat 10/31

11:54 am-4:03 pm

Nonstop3h 09m

Chicago O'Hare Intl

Tue 11/3

1:05 pm-4:57 pm

1 stop4h 52m

$524

AspenChicago

ASE - MDW

ASEMDW

Aspen Pitkin County

Wed 8/19

7:20 am-4:15 pm

1 stop7h 55m

Chicago Midway

Sun 8/23

6:05 am-11:23 am

1 stop6h 18m

$854

AspenChicago

ASE - MDW

ASEMDW

Aspen Pitkin County

Fri 9/4

7:20 am-6:33 pm

2 stops10h 13m

Chicago Midway

Tue 9/8

6:05 am-11:21 am

1 stop6h 16m

$921

AspenChicago

ASE - MDW

ASEMDW

Aspen Pitkin County

Sat 9/12

7:35 am-4:57 pm

2 stops8h 22m

Chicago Midway

Mon 9/14

6:05 am-11:21 am

1 stop6h 16m

$1,121

AspenChicago

ASE - MDW

ASEMDW

Aspen Pitkin County

Sat 9/19

7:35 am-6:22 pm

2 stops9h 47m

Chicago Midway

Sun 9/20

6:05 am-11:21 am

1 stop6h 16m

$1,179

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/2

Showing 1-10 of 23 resultsSorted by cheapest first
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 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 August 3, 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.

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 August 3, 2026.

The most flights from ASE to CHI are scheduled on a Tuesday (7 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (3 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 August 3, 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
10,058 reviews

Crew

8.1

Comfort

7.3

Food

6.7

Overall

7.4

Entertainment

7.1

Boarding

7.7

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
10,058 reviews
United Airlines
7.4
Good
10,058 reviews

Crew

8.1

Comfort

7.3

Food

6.7

Overall

7.4

Entertainment

7.1

Boarding

7.7

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
7.1
Good
11,842 reviews
United Airlines
7.4
Good
10,058 reviews

Crew

8.1

Comfort

7.3

Food

6.7

Overall

7.4

Entertainment

7.1

Boarding

7.7

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 $403, Delta can have you in Chicago from Aspen in 6h 47m. Aspen and Chicago are separated by a distance of 1017 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, United Airlines ($335), and American Airlines ($343) offers the cheapest pricing from Aspen to Chicago.

  • 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 (72%), SkyWest Airlines (66%), Qatar Airways( 64%).

  • What are the cheapest flights from Aspen to Chicago?

    While on average a flight from Aspen to Chicago is generally $1,040, our data shows the cheapest flight currently is $209. When looking at the most popular route, (Aspen Pitkin County - Chicago O'Hare Intl), you can expect to pay $353 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.

See more FAQs

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Benton Harbor
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
Porter

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 August 3, 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$335Average$449FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$343Average$414FlexibilityNo cancel feeOn-time71%

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