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$151+ 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 6/26. Fares are subject to change and may not be available on all flights or dates of travel.
ASE — CHI
juin 17 — juin 241
mar. 6/17
mar. 6/24
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 juin 12, 2025.

Round-trip from

$239
(United Airlines)

One-way from

$151
(American Airlines)

Popular in

March

Cheapest in

April

Average price

$404

Good round-trip deal

$365 or less

Good one-way deal

$180 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. 6% potential increase in price ($32 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($14 potential savings vs. average RT price).
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Average for round-trip flights in June 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 juin 12, 2025.

This United Airlines deal was found by Cheapflights users on 6/10. 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.
jeu. 8/212:40 pmASE - ORD
1 stop7h 02mUnited Airlines
lun. 8/257:35 pmORD - ASE
Nonstop3h 10mUnited Airlines
Deal found 6/10$239
This American Airlines deal was found by Cheapflights users on 6/10. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mer. 7/91:35 pmASE - ORD
1 stop6h 49mAmerican Airlines
jeu. 7/1010:54 amORD - ASE
Nonstop3h 11mAmerican Airlines
Deal found 6/10$360
This Delta deal was found by Cheapflights users on 6/10. 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.
jeu. 8/217:16 amASE - MDW
2 stops10h 21mDelta
lun. 8/256:00 amMDW - ASE
1 stop6h 21mDelta
Deal found 6/10$761
This Delta deal was found by Cheapflights users on 6/10. 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.
sam. 6/148:05 amASE - ORD
2 stops11h 06mDelta
sam. 6/215:35 amORD - ASE
1 stop6h 47mDelta
Deal found 6/10$894

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 juin 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. 8/21

2:40 pm-10:42 pm

1 stop7h 02m

Chicago O'Hare Intl

lun. 8/25

7:35 pm-9:45 pm

Nonstop3h 10m

$239

AspenChicago

ASE - ORD

ASEORD

Aspen Pitkin County

mer. 7/9

1:35 pm-9:24 pm

1 stop6h 49m

Chicago O'Hare Intl

jeu. 7/10

10:54 am-1:05 pm

Nonstop3h 11m

$360

AspenChicago

ASE - MDW

ASEMDW

Aspen Pitkin County

jeu. 8/21

7:16 am-6:37 pm

2 stops10h 21m

Chicago Midway

lun. 8/25

6:00 am-11:21 am

1 stop6h 21m

$761

AspenChicago

ASE - ORD

ASEORD

Aspen Pitkin County

jeu. 8/21

7:16 am-7:28 pm

2 stops11h 12m

Chicago O'Hare Intl

lun. 8/25

5:45 am-11:21 am

1 stop6h 36m

$951

AspenChicago

ASE - ORD

ASEORD

Aspen Pitkin County

jeu. 6/26

1:34 pm-9:24 pm

1 stop6h 50m

$151

AspenChicago

ASE - ORD

ASEORD

Aspen Pitkin County

jeu. 6/26

6:15 pm-12:30 am

1 stop5h 15m

$191

AspenChicago

ASE - MDW

ASEMDW

Aspen Pitkin County

jeu. 6/26

8:05 am-6:41 pm

2 stops9h 36m

$385

AspenChicago

ASE - ORD

ASEORD

Aspen Pitkin County

mer. 7/9

8:05 am-8:15 pm

2 stops11h 10m

$605

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/10

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 juin 12, 2025.

It’s optimal to fly from Aspen to Chicago in the afternoon. By choosing this option you can save up to 15% 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 juin 12, 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).

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 juin 12, 2025.
Delta
8.0
Very good
7,950 reviews

Entertainment

7.9

Crew

8.5

Overall

8.0

Comfort

7.9

Boarding

8.2

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Delta
8.0
Very good
7,950 reviews
Delta
8.0
Very good
7,950 reviews

Entertainment

7.9

Crew

8.5

Overall

8.0

Comfort

7.9

Boarding

8.2

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
United Airlines
7.4
Good
8,790 reviews
Delta
8.0
Very good
7,950 reviews

Entertainment

7.9

Crew

8.5

Overall

8.0

Comfort

7.9

Boarding

8.2

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,950 reviews

Entertainment

7.9

Crew

8.5

Overall

8.0

Comfort

7.9

Boarding

8.2

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

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.

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

    According to our current data, United Airlines ($239), American Airlines ($360), and Delta ($761) offers the cheapest pricing from Aspen to Chicago. Users have found that United Airlines is 49% cheaper than the other options available to this destination.

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

    $151 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 $191 and $385, 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 (58%), SkyWest Airlines (56%), Lufthansa( 52%).

  • What are the cheapest flights from Aspen to Chicago?

    While on average a flight from Aspen to Chicago is generally $520, our data shows the cheapest flight currently is $140. When looking at the most popular route, (Aspen Pitkin County - Chicago O'Hare Intl), you can expect to pay $239 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 Aspen?

Book flights to Aspen if you plan to visit one of these locations
Merrillville
Lansing
Benton Harbor
Porter
Hammond
Valparaiso
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 juin 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$235Average$361FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$315Average$463FlexibilityNo cancel feeOn-time69%

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