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$258+ 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 4/25. Fares are subject to change and may not be available on all flights or dates of travel.
ASE — CHI
Feb 27 — Mar 61
Thu 2/27
Thu 3/6
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 February 22, 2025.

Round-trip from

$329
(American Airlines)

One-way from

$258
(American Airlines)

Popular in

February

Cheapest in

May

Average price

$1,514

Good round-trip deal

$423 or less

Good one-way deal

$475 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. 35% potential increase in price ($318 potential increase over avg. RT price).
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Cheapest flight prices on average. 17% potential price decrease ($86 potential savings vs. average RT price).
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Average for round-trip flights in February 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 February 22, 2025.

This American Airlines deal was found by Cheapflights users on 2/22. 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 3/2111:35 amASE - ORD
Nonstop2h 58mAmerican Airlines
Sun 3/3011:51 amORD - ASE
Nonstop3h 13mAmerican Airlines
Deal found 2/22$329
This United Airlines deal was found by Cheapflights users on 2/21. 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 4/96:13 pmASE - ORD
1 stop5h 22mUnited Airlines
Mon 4/147:10 amORD - ASE
1 stop6h 21mUnited Airlines
Deal found 2/21$349
This Delta deal was found by Cheapflights users on 2/21. 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 4/92:55 pmASE - MDW
1 stop6h 26mDelta
Mon 4/146:04 amMDW - ASE
1 stop6h 34mDelta
Deal found 2/21$364
This Delta deal was found by Cheapflights users on 2/21. 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 6/187:45 amASE - ORD
2 stops11h 49mDelta
Fri 6/206:00 amORD - ASE
1 stop6h 23mDelta
Deal found 2/21$1,044

Find flights from Aspen to Chicago within your budget

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 22, 2025.

Fly from

Aspen

Fly to

Chicago

Route

Depart

Return

Price

AspenChicago

ASE - ORD

ASEORD

Aspen Pitkin County

Fri 3/21

11:35 am-3:33 pm

Nonstop2h 58m

Chicago O'Hare Intl

Sun 3/30

11:51 am-2:04 pm

Nonstop3h 13m

$329

AspenChicago

ASE - ORD

ASEORD

Aspen Pitkin County

Wed 4/9

6:13 pm-12:35 am

1 stop5h 22m

Chicago O'Hare Intl

Mon 4/14

7:10 am-12:31 pm

1 stop6h 21m

$349

AspenChicago

ASE - MDW

ASEMDW

Aspen Pitkin County

Wed 4/9

2:55 pm-10:21 pm

1 stop6h 26m

Chicago Midway

Mon 4/14

6:04 am-11:38 am

1 stop6h 34m

$364

AspenChicago

ASE - ORD

ASEORD

Aspen Pitkin County

Wed 6/18

7:45 am-8:34 pm

2 stops11h 49m

Chicago O'Hare Intl

Fri 6/20

6:00 am-11:23 am

1 stop6h 23m

$1,044

AspenChicago

ASE - ORD

ASEORD

Aspen Pitkin County

Fri 4/25

12:29 pm-7:05 am

2 stops17h 36m

$258

AspenChicago

ASE - MDW

ASEMDW

Aspen Pitkin County

Wed 4/16

1:39 pm-10:26 pm

1 stop7h 47m

$295

AspenChicago

ASE - ORD

ASEORD

Aspen Pitkin County

Wed 4/23

7:00 am-8:25 pm

2 stops12h 25m

$299

AspenChicago

ASE - ORD

ASEORD

Aspen Pitkin County

Fri 4/18

1:39 pm-8:50 pm

1 stop6h 11m

$320

AspenChicago

ASE - ORD

ASEORD

Aspen Pitkin County

Tue 3/11

1:04 pm-7:37 pm

3 stops29h 33m

$985

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/21

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.

Travel insights for flights from Aspen to Chicago

Get recent, data-driven insights about flights from Aspen to Chicago including ideal travel times, pricing trends, and more.

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 February 22, 2025.

It’s optimal to fly from Aspen to Chicago in the afternoon. By choosing this option you can save up to 13% on the cost of your flight, compared to a flight in the morning.

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 February 22, 2025.

The most flights from ASE to CHI are scheduled on a Monday (7 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (6 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 February 22, 2025.
Alaska Airlines
8.0
Very good
9,700 reviews

Overall

8.0

Comfort

7.9

Entertainment

7.1

Food

7.1

Crew

8.5

Boarding

8.2

Reviews

1 / 20

10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

Alaska Airlines
8.0
Very good
9,700 reviews
Alaska Airlines
8.0
Very good
9,700 reviews

Overall

8.0

Comfort

7.9

Entertainment

7.1

Food

7.1

Crew

8.5

Boarding

8.2

Reviews

1 / 20

10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

Delta
8.0
Very good
8,203 reviews
Alaska Airlines
8.0
Very good
9,700 reviews

Overall

8.0

Comfort

7.9

Entertainment

7.1

Food

7.1

Crew

8.5

Boarding

8.2

Reviews

1 / 20

10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

United Airlines
7.4
Good
8,754 reviews
Alaska Airlines
8.0
Very good
9,700 reviews

Overall

8.0

Comfort

7.9

Entertainment

7.1

Food

7.1

Crew

8.5

Boarding

8.2

Reviews

1 / 20

10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

American Airlines
7.2
Good
10,000 reviews
Alaska Airlines
8.0
Very good
9,700 reviews

Overall

8.0

Comfort

7.9

Entertainment

7.1

Food

7.1

Crew

8.5

Boarding

8.2

Reviews

1 / 20

10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

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 6 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, American Airlines ($329), United Airlines ($349), and Delta ($364) offers the cheapest pricing from Aspen to Chicago. Users have found that American Airlines is 42% cheaper than the other options available to this destination.

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

    $258 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 Delta and United Airlines, with prices starting from $295 and $299, 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: Lufthansa (75%), Qatar Airways (58%), United Airlines( 47%).

  • What are the cheapest flights from Aspen to Chicago?

    While on average a flight from Aspen to Chicago is generally $526, our data shows the cheapest flight currently is $334. When looking at the most popular route, (Aspen Pitkin County - Chicago O'Hare Intl), you can expect to pay $339 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
New Buffalo
Hammond
Benton Harbor
Porter
Lansing
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 February 22, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$235Average$398FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$302Average$463FlexibilityNo cancel feeOn-time69%
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