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

According to our current data, American Airlines ($210), United Airlines ($249), and Delta ($609) offers the cheapest pricing from Aspen to Chicago. Users have found that American Airlines is 55% cheaper than the other options available to this destination.

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

$110 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 $284 and $540, respectively.

What is the cheapest day to fly from Aspen to Chicago?

Travelers seeking maximum savings on their Aspen to Chicago flight should consider departing on Monday at noon when fares are most often at their lowest. Sunday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

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.

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).

What are the cheapest flights from Aspen to Chicago?

While on average a flight from Aspen to Chicago is generally $625, 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 $264 for that flight.

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 (70%), SkyWest Airlines (65%), Lufthansa( 64%).

What is the cheapest day to fly round-trip from Aspen to Chicago?

Departing on a Wednesday is a good option for securing a great price. You can expect to save up to 86% when planning your travel around this day of the week.

What is the cheapest month to fly from Aspen to Chicago?

April can be a great time to fly to Chicago from Aspen with a flight ticket averaging about $473. Cheapflights users have found deals in the month of April for as cheap as $329. The most expensive prices can be found in the month of March.

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 3 outbound flights to Chicago per day from 2 airlines. Aspen Pitkin County is conveniently located just 3.5 mi from Aspen’s city center.

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.

$110+ Flights from Aspen to Chicago

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Cheap flight deals from Aspen to Chicago

Round-trip from	$210 (American Airlines)
One-way from	$110 (American Airlines)
Popular in	March
Cheapest in	April
Average price	$410
Good round-trip deal	$410 or less
Good one-way deal	$278 or less

From Aspen Pitkin County to Chicago (CHI)

Search Deals

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 ($30 potential increase over avg. RT price).

Search Deals

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 July 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 July 2, 2025.

Wed 9/1012:14 pmASE - ORD

Nonstop2h 58mAmerican Airlines

Sat 9/139:31 amORD - ASE

Nonstop3h 10mAmerican Airlines

Deal found 7/2

$210

Thu 7/246:15 pmASE - ORD

1 stop5h 15mUnited Airlines

Mon 7/285:00 amORD - ASE

1 stop4h 42mUnited Airlines

Deal found 7/2

$249

Wed 9/107:16 amASE - ORD

2 stops12h 07mDelta

Sat 9/135:30 amORD - ASE

1 stop6h 48mDelta

Deal found 7/2

$609

Fri 10/107:45 amASE - MDW

1 stop7h 38mDelta

Sun 10/126:00 amMDW - ASE

1 stop6h 39mDelta

Deal found 7/2

$748

Best flights from Aspen to Chicago
Discover carefully curated flight deals from Aspen to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated July 2, 2025.

Wed 9/1012:14 pmASE - ORD

Nonstop2h 58mAmerican Airlines

Sat 9/139:31 amORD - ASE

Nonstop3h 10mAmerican Airlines

Deal found 7/2

$210

Thu 7/246:15 pmASE - ORD

1 stop5h 15mUnited Airlines

Mon 7/285:00 amORD - ASE

1 stop4h 42mUnited Airlines

Deal found 7/2

$249

Wed 9/107:16 amASE - ORD

2 stops12h 07mDelta

Sat 9/135:30 amORD - ASE

1 stop6h 48mDelta

Deal found 7/1

$609

Fri 10/107:45 amASE - MDW

1 stop7h 38mDelta

Sun 10/126:00 amMDW - ASE

1 stop6h 39mDelta

Deal found 7/2

$748

Last-minute flights from Aspen to Chicago
Discover last-minute flight deals from Aspen to Chicago. Data last updated July 2, 2025 and is based on user searches.

Wed 7/912:06 pmASE - ORD

Nonstop2h 58mAmerican Airlines

Sat 7/125:00 amORD - ASE

1 stop5h 50mAmerican Airlines

Deal found 6/30

$384

Wed 7/98:05 amASE - MDW

2 stops9h 35mDelta

Fri 7/116:00 amMDW - ASE

1 stop6h 21mDelta

Deal found 6/30

$1,174

Fri 7/1111:36 amASE - ORD

1 stop5h 48mUnited Airlines

Tue 7/225:00 amORD - ASE

1 stop4h 42mUnited Airlines

Deal found 7/1

$382

Sat 7/194:35 pmASE - ORD

1 stop6h 11mAmerican Airlines

Tue 7/2210:54 amORD - ASE

Nonstop3h 11mAmerican Airlines

Deal found 7/2

$294

Thu 7/246:15 pmASE - ORD

1 stop5h 15mUnited Airlines

Mon 7/285:00 amORD - ASE

1 stop4h 42mUnited Airlines

Deal found 7/2

$249

Fri 8/297:16 amASE - MDW

1 stop7h 26mDelta

Mon 9/16:00 amMDW - ASE

1 stop6h 21mDelta

Deal found 6/30

$789

One-way flights from Aspen to Chicago
Search for one-way flight options from Aspen to Chicago. Find affordable one-way fares based on user searches. Data last updated July 2, 2025.

Fri 9/512:14 pmASE - ORD

Nonstop2h 58mAmerican Airlines

Deal found 7/1

$110

Fri 8/16:15 pmASE - ORD

1 stop5h 15mUnited Airlines

Deal found 7/1

$284

Fri 8/297:16 amASE - MDW

1 stop7h 26mDelta

Deal found 6/30

$540

Cheapflights Fare Finder

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

AspenChicago

ASE - ORD

ASEORD

Aspen Pitkin County

Wed 9/10

12:14 pm-4:12 pm

Nonstop2h 58m

Chicago O'Hare Intl

Sat 9/13

9:31 am-11:41 am

Nonstop3h 10m

$210

AspenChicago

ASE - ORD

ASEORD

Aspen Pitkin County

Thu 7/24

6:15 pm-12:30 am

1 stop5h 15m

Chicago O'Hare Intl

Mon 7/28

5:00 am-8:42 am

1 stop4h 42m

$249

AspenChicago

ASE - ORD

ASEORD

Aspen Pitkin County

Wed 9/10

7:16 am-8:23 pm

2 stops12h 07m

Chicago O'Hare Intl

Sat 9/13

5:30 am-11:18 am

1 stop6h 48m

$609

AspenChicago

ASE - MDW

ASEMDW

Aspen Pitkin County

Fri 10/10

7:45 am-4:23 pm

1 stop7h 38m

Chicago Midway

Sun 10/12

6:00 am-11:39 am

1 stop6h 39m

$748

AspenChicago

ASE - ORD

ASEORD

Aspen Pitkin County

Fri 9/5

12:14 pm-4:12 pm

Nonstop2h 58m

$110

AspenChicago

ASE - ORD

ASEORD

Aspen Pitkin County

Fri 8/1

6:15 pm-12:30 am

1 stop5h 15m

$284

AspenChicago

ASE - MDW

ASEMDW

Aspen Pitkin County

Fri 8/29

7:16 am-3:42 pm

1 stop7h 26m

$540

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/1

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?

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

The most flights from ASE to CHI are scheduled on a Monday (4 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (2 on average).

How much does it cost to fly round-trip from Aspen to Chicago?

Reviews of airlines servicing Chicago

Read through reviews of airlines operating flights from Aspen to Chicago, such as Delta, United Airlines, and American Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.

Delta

8.0

Very good

7,983 reviews

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

7,983 reviews

Delta

8.0

Very good

7,983 reviews

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

8,861 reviews

Delta

8.0

Very good

7,983 reviews

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

7,983 reviews

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

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 3 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 ($210), United Airlines ($249), and Delta ($609) offers the cheapest pricing from Aspen to Chicago. Users have found that American Airlines is 55% cheaper than the other options available to this destination.
What are the cheapest airlines to fly from Aspen to Chicago one-way?
$110 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 $284 and $540, 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 (70%), SkyWest Airlines (65%), Lufthansa( 64%).
What are the cheapest flights from Aspen to Chicago?
While on average a flight from Aspen to Chicago is generally $625, 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 $264 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

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Porter

Hammond

Valparaiso

Chesterton

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Top 2 airlines flying from Aspen to Chicago

Airline	Cheapest	Average	Flexibility	On-time
American Airlines	Cheapest$172	Average$361	FlexibilityNo cancel fee	On-time71%
United Airlines	Cheapest$302	Average$469	FlexibilityNo cancel fee	On-time69%

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$110+ 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 9/5. Fares are subject to change and may not be available on all flights or dates of travel.

Find cheap flights from Aspen to Chicago with Cheapflights

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2. Select your favorite providers

3. Compare prices and book

Cheap flight deals from Aspen to Chicago

Round-trip from

One-way from

Popular in

Cheapest in

Average price

Good round-trip deal

Good one-way deal

Find flight deals from Aspen to Chicago

Cheapest flights from Aspen to ChicagoExplore 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 July 2, 2025.

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 July 2, 2025.

Cheapflights Fare Finder

Use the filters below to find and compare flights from Aspen to Chicago that are best for you.

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.

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?

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 July 2, 2025.

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 July 2, 2025.

How much does it cost to fly round-trip from Aspen to Chicago?

Reviews of airlines servicing Chicago

Read through reviews of airlines operating flights from Aspen to Chicago, such as Delta, United Airlines, and American Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.

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?

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

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

What are the most reliable airlines from Aspen to Chicago?

What are the cheapest flights from Aspen to Chicago?

Can I find deals for flights from Aspen to Chicago that include hotel bookings?

How can I find direct flights from Aspen to Chicago?

Can I find deals for business class flights from Aspen to Chicago?

What is the cheapest month to book a flight from Aspen to Chicago?

Traveling to a place near Aspen?

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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.

Top 2 airlines flying from Aspen to Chicago

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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 July 2, 2025.