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$145+ 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 8/22. Fares are subject to change and may not be available on all flights or dates of travel.
ASE — CHI
Apr 2 — Apr 91
Wed 4/2
Wed 4/9
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 March 28, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$259
(United Airlines)

One-way from

$145
(American Airlines)

Popular in

March

Cheapest in

May

Average price

$621

Good round-trip deal

$458 or less

Good one-way deal

$364 or less
Provider with most accurate pricing for Aspen Pitkin County-Chicago (CHI) flight deals.
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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)
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Highest demand for flights based on searches. 11% potential increase in price ($60 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($14 potential savings vs. average RT price).
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Average for round-trip flights in March 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 March 28, 2025.

This United Airlines deal was found by Cheapflights users on 3/27. 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 7/256:15 pmASE - ORD
1 stop5h 15mUnited Airlines
Sun 8/35:00 amORD - ASE
1 stop4h 42mUnited Airlines
Deal found 3/27$259
This American Airlines deal was found by Cheapflights users on 3/27. 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 6/510:22 amASE - ORD
1 stop7h 23mAmerican Airlines
Wed 6/1110:50 amORD - ASE
Nonstop3h 13mAmerican Airlines
Deal found 3/27$344
This Delta deal was found by Cheapflights users on 3/27. 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 6/57:45 amASE - ORD
2 stops10h 35mDelta
Wed 6/115:45 amORD - ASE
1 stop6h 37mDelta
Deal found 3/27$624
This Delta deal was found by Cheapflights users on 3/27. 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 4/171:39 pmASE - MDW
1 stop7h 43mDelta
Sun 4/206:04 amMDW - ASE
1 stop6h 34mDelta
Deal found 3/27$1,009

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 March 28, 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

Fri 7/25

6:15 pm-12:30 am

1 stop5h 15m

Chicago O'Hare Intl

Sun 8/3

5:00 am-8:42 am

1 stop4h 42m

$259

AspenChicago

ASE - ORD

ASEORD

Aspen Pitkin County

Thu 6/5

10:22 am-6:45 pm

1 stop7h 23m

Chicago O'Hare Intl

Wed 6/11

10:50 am-1:03 pm

Nonstop3h 13m

$344

AspenChicago

ASE - ORD

ASEORD

Aspen Pitkin County

Thu 6/5

7:45 am-7:20 pm

2 stops10h 35m

Chicago O'Hare Intl

Wed 6/11

5:45 am-11:22 am

1 stop6h 37m

$624

AspenChicago

ASE - MDW

ASEMDW

Aspen Pitkin County

Thu 4/17

1:39 pm-10:22 pm

1 stop7h 43m

Chicago Midway

Sun 4/20

6:04 am-11:38 am

1 stop6h 34m

$1,009

AspenChicago

ASE - ORD

ASEORD

Aspen Pitkin County

Fri 8/22

12:21 pm-4:10 pm

Nonstop2h 49m

$145

AspenChicago

ASE - ORD

ASEORD

Aspen Pitkin County

Fri 8/22

2:50 pm-9:32 pm

1 stop5h 42m

$195

AspenChicago

ASE - MDW

ASEMDW

Aspen Pitkin County

Fri 8/22

7:45 am-2:56 pm

1 stop6h 11m

$480

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/27

  • Most accurate provider: When it comes to deals on Aspen-Chicago flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Aspen-Chicago flight deals on Cheapflights vs. eDreams >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 eDreams the most. eDreams 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 $245). Flying from Aspen to Chicago in March is currently the most expensive (average of $323). 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 March 28, 2025.

It’s optimal to fly from Aspen to Chicago in the afternoon. By choosing this option you can save up to 14% on the cost of your flight, compared to a flight in the morning.

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 March 28, 2025.
Delta
8.0
Very good
7,897 reviews

Boarding

8.2

Comfort

8.0

Food

7.3

Entertainment

7.9

Overall

8.0

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
Delta
8.0
Very good
7,897 reviews
Delta
8.0
Very good
7,897 reviews

Boarding

8.2

Comfort

8.0

Food

7.3

Entertainment

7.9

Overall

8.0

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
United Airlines
7.4
Good
8,603 reviews
Delta
8.0
Very good
7,897 reviews

Boarding

8.2

Comfort

8.0

Food

7.3

Entertainment

7.9

Overall

8.0

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,897 reviews

Boarding

8.2

Comfort

8.0

Food

7.3

Entertainment

7.9

Overall

8.0

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

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.

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

    According to our current data, United Airlines ($259), American Airlines ($344), and Delta ($624) offers the cheapest pricing from Aspen to Chicago. Users have found that United Airlines is 44% cheaper than the other options available to this destination.

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

    $145 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 $195 and $480, 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 (65%), American Airlines( 59%).

  • What are the cheapest flights from Aspen to Chicago?

    While on average a flight from Aspen to Chicago is generally $709, our data shows the cheapest flight currently is $196. When looking at the most popular route, (Aspen Pitkin County - Chicago O'Hare Intl), you can expect to pay $259 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 $323). 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 March 28, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$235Average$361FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$302Average$457FlexibilityNo cancel feeOn-time69%
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