HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chicago

$208+ 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 11/19. Fares are subject to change and may not be available on all flights or dates of travel.
ASE — CHI
Dec 5 — Dec 121
Fri 12/5
Fri 12/12
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Aspen to Chicago with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 November 5, 2025.

This United Airlines deal was found by Cheapflights users on 11/5. 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 12/184:15 pmASE - ORD
Nonstop3h 05mUnited Airlines
Tue 12/234:47 pmORD - ASE
Nonstop3h 30mUnited Airlines
Deal found 11/5$311
This United Airlines deal was found by Cheapflights users on 11/4. 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 12/59:52 amASE - ORD
1 stop6h 06mUnited Airlines
Sun 12/73:35 pmORD - ASE
Nonstop3h 14mUnited Airlines
Deal found 11/4$321
This Delta deal was found by Cheapflights users on 11/4. 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 11/191:05 pmASE - ORD
1 stop8h 25mDelta
Sun 11/235:23 amORD - ASE
1 stop6h 58mDelta
Deal found 11/4$335
This American Airlines deal was found by Cheapflights users on 11/4. 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.
Mon 12/2912:01 pmASE - ORD
Nonstop3h 11mAmerican Airlines
Sat 1/39:52 amORD - ASE
Nonstop3h 34mAmerican Airlines
Deal found 11/4$349
This American Airlines deal was found by Cheapflights users on 11/2. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/137:34 amASE - ORD
1 stop8h 43mAmerican Airlines
Sun 11/165:18 amORD - ASE
1 stop7h 24mAmerican Airlines
Deal found 11/2$372
This United Airlines deal was found by Cheapflights users on 11/5. 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 12/49:00 amASE - ORD
Nonstop3h 12mUnited Airlines
Sun 12/73:35 pmORD - ASE
Nonstop3h 14mUnited Airlines
Deal found 11/5$391
This Delta deal was found by Cheapflights users on 11/5. 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 11/201:05 pmASE - ORD
1 stop7h 51mDelta
Mon 11/245:23 amORD - ASE
1 stop6h 58mDelta
Deal found 11/5$399
This Delta deal was found by Cheapflights users on 11/5. 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 12/41:20 pmASE - ORD
2 stops19h 40mDelta
Sun 12/75:30 amORD - ASE
1 stop7h 07mDelta
Deal found 11/5$410
This Delta deal was found by Cheapflights users on 11/4. 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 12/51:20 pmASE - ORD
1 stop7h 36mDelta
Sun 12/75:30 amORD - ASE
1 stop7h 07mDelta
Deal found 11/4$415
This Delta deal was found by Cheapflights users on 11/4. 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 11/67:21 amASE - MDW
2 stops10h 04mDelta
Sun 11/96:00 amMDW - ASE
1 stop6h 21mDelta
Deal found 11/4$985

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 November 5, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
1 star

Round-trip from

$311
(United Airlines)

One-way from

$211
(United Airlines)

Popular in

December

Cheapest in

April

Average price

$398

Good round-trip deal

$333 or less

Good one-way deal

$320 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
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. 3% potential price decrease ($17 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2025
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 November 5, 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

Thu 12/18

4:15 pm-8:20 pm

Nonstop3h 05m

Chicago O'Hare Intl

Tue 12/23

4:47 pm-7:17 pm

Nonstop3h 30m

$311

AspenChicago

ASE - ORD

ASEORD

Aspen Pitkin County

Fri 12/5

9:52 am-4:58 pm

1 stop6h 06m

Chicago O'Hare Intl

Sun 12/7

3:35 pm-5:49 pm

Nonstop3h 14m

$321

AspenChicago

ASE - ORD

ASEORD

Aspen Pitkin County

Fri 12/12

12:40 pm-4:39 pm

Nonstop2h 59m

Chicago O'Hare Intl

Tue 12/16

7:10 am-10:38 am

1 stop4h 28m

$321

AspenChicago

ASE - ORD

ASEORD

Aspen Pitkin County

Wed 11/19

1:05 pm-10:30 pm

1 stop8h 25m

Chicago O'Hare Intl

Sun 11/23

5:23 am-11:21 am

1 stop6h 58m

$335

AspenChicago

ASE - ORD

ASEORD

Aspen Pitkin County

Mon 12/29

12:01 pm-4:12 pm

Nonstop3h 11m

Chicago O'Hare Intl

Sat 1/3

9:52 am-12:26 pm

Nonstop3h 34m

$349

AspenChicago

ASE - ORD

ASEORD

Aspen Pitkin County

Thu 3/26

3:50 pm-7:50 pm

Nonstop3h 00m

Chicago O'Hare Intl

Mon 3/30

1:10 pm-3:29 pm

Nonstop3h 19m

$391

AspenChicago

ASE - ORD

ASEORD

Aspen Pitkin County

Thu 12/4

9:00 am-1:12 pm

Nonstop3h 12m

Chicago O'Hare Intl

Sun 12/7

3:35 pm-5:49 pm

Nonstop3h 14m

$391

AspenChicago

ASE - ORD

ASEORD

Aspen Pitkin County

Thu 11/20

1:05 pm-9:56 pm

1 stop7h 51m

Chicago O'Hare Intl

Mon 11/24

5:23 am-11:21 am

1 stop6h 58m

$399

AspenChicago

ASE - MDW

ASEMDW

Aspen Pitkin County

Thu 3/26

1:50 pm-9:46 pm

1 stop6h 56m

Chicago Midway

Mon 3/30

6:00 am-2:19 pm

1 stop9h 19m

$774

AspenChicago

ASE - ORD

ASEORD

Aspen Pitkin County

Wed 11/19

1:05 pm-10:30 pm

1 stop8h 25m

$208

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/5

Showing 1-10 of 27 results
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 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 $183). Flying from Aspen to Chicago in April is currently the most expensive (average of $361). 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 November 5, 2025.

It’s optimal to fly from Aspen to Chicago in the evening. By choosing this option you can save up to 62% on the cost of your flight, compared to a flight at noon.

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 November 5, 2025.
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
9,002 reviews

Comfort

7.3

Crew

8.1

Boarding

7.7

Entertainment

7.1

Food

6.6

Overall

7.4

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
United Airlines
7.4
Good
9,002 reviews
United Airlines
7.4
Good
9,002 reviews

Comfort

7.3

Crew

8.1

Boarding

7.7

Entertainment

7.1

Food

6.6

Overall

7.4

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
American Airlines
7.2
Good
11,042 reviews
United Airlines
7.4
Good
9,002 reviews

Comfort

7.3

Crew

8.1

Boarding

7.7

Entertainment

7.1

Food

6.6

Overall

7.4

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.

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 0 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 $311, United Airlines can have you in Chicago from Aspen in 3h 05m. Aspen and Chicago are separated by a distance of 1010 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, American Airlines ($172), and United Airlines ($289) offers the cheapest pricing from Aspen to Chicago. Users have found that American Airlines is 61% cheaper than the other options available to this destination.

  • 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 (86%), SkyWest Airlines (86%), United Airlines( 86%).

  • What are the cheapest flights from Aspen to Chicago?

    While on average a flight from Aspen to Chicago is generally $822, our data shows the cheapest flight currently is $210. When looking at the most popular route, (Aspen Pitkin County - Chicago O'Hare Intl), you can expect to pay $311 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 $183). Flying from Aspen to Chicago in April is currently the most expensive (average of $361). 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 Chicago?

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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Aspen to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
Denver to O'Hare Intl flights
Denver to Midway flights
Denver to St. Louis flights
Colorado Springs to O'Hare Intl flights
Denver to Peoria flights
Denver to Moline flights
Colorado Springs to Midway flights
Vail to O'Hare Intl flights
Denver to Bloomington flights
Denver to Rockford flights
Grand Junction to O'Hare Intl flights
Colorado Springs to St. Louis flights
Montrose to O'Hare Intl flights
Durango to O'Hare Intl flights
Vail to St. Louis flights
Denver to Evansville flights
Denver to Springfield flights
Montrose to St. Louis flights
Aspen to O'Hare Intl flights
Denver to Decatur flights
Durango to St. Louis flights
Colorado Springs to Peoria flights
Gunnison to O'Hare Intl flights
Grand Junction to St. Louis flights
Colorado Springs to Moline flights
Hayden to O'Hare Intl flights
Aspen to Midway flights
Aspen to St. Louis flights
Montrose to Midway flights
Denver to Champaign flights
Grand Junction to Midway flights
Gunnison to St. Louis flights
Hayden to St. Louis flights
Denver to Dubuque flights
Montrose to Peoria flights
Grand Junction to Peoria flights
Grand Junction to Bloomington flights
Colorado Springs to Evansville flights
Vail to Midway flights
Colorado Springs to Bloomington flights
Hayden to Moline flights
Durango to Moline flights
Colorado Springs to Springfield flights
Colorado Springs to Champaign flights
Durango to Midway flights
Montrose to Springfield flights

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 November 5, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$172Average$404FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$289Average$409FlexibilityNo cancel feeOn-time69%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.