$217+ Cheap flights from Aspen (ASE) to Chicago (CHI)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 2/9. Fares are subject to change and may not be available on all flights or dates of travel.
ASE — CHI
Nov 24 — Dec 11
Round-trip
1 adult, Economy
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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.Cheap flight deals from Aspen to Chicago
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Best
Last-minute
One-way
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 October 25, 2026.
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 October 25, 2026.
This United Airlines deal was found by Cheapflights users on 10/20. 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.
Sun 11/153:18 pm -
1 stop6h 28m
Sun 11/227:00 am -
1 stop4h 42m
Deal found 10/20![United Airlines logo]()
$496
This United Airlines deal was found by Cheapflights users on 10/20. 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.
Tue 12/112:45 pm -
Nonstop3h 00m
Fri 12/44:15 pm -
Nonstop3h 22m
Deal found 10/20![United Airlines logo]()
$504
This American Airlines deal was found by Cheapflights users on 10/23. 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.
Tue 10/2712:48 pm -
Nonstop3h 17m
Sun 11/13:00 pm -
1 stop6h 17m
Deal found 10/23![American Airlines logo]()
$519
This United Airlines deal was found by Cheapflights users on 10/22. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/1011:23 am -
1 stop7h 42m
Sat 11/148:47 am -
Nonstop3h 26m
Deal found 10/22![United Airlines logo]()
$524
This United Airlines deal was found by Cheapflights users on 10/22. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/61:30 pm -
1 stop5h 59m
Tue 11/1010:55 am -
1 stop4h 42m
Deal found 10/22![United Airlines logo]()
$529
This Delta deal was found by Cheapflights users on 10/21. 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.
Thu 11/57:30 am -
2 stops12h 00m
Sun 11/85:27 am -
1 stop6h 57m
Deal found 10/21![Delta logo]()
$534
This Delta deal was found by Cheapflights users on 10/22. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/67:30 am -
2 stops12h 00m
Tue 11/105:30 am -
1 stop7h 13m
Deal found 10/22![Delta logo]()
$554
This United Airlines deal was found by Cheapflights users on 10/22. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/71:30 pm -
1 stop5h 01m
Sun 11/87:00 am -
1 stop4h 42m
Deal found 10/22![United Airlines logo]()
$564
This Delta deal was found by Cheapflights users on 10/22. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/77:30 am -
1 stop8h 28m
Mon 11/95:30 am -
1 stop7h 13m
Deal found 10/22![Delta logo]()
$584
This United Airlines deal was found by Cheapflights users on 10/20. 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.
Mon 11/306:09 pm -
1 stop4h 50m
Fri 12/44:15 pm -
Nonstop3h 22m
Deal found 10/20![United Airlines logo]()
$585
This United Airlines deal was found by Cheapflights users on 10/21. 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.
Thu 10/228:21 am -
Nonstop3h 08m
Thu 10/227:50 pm -
Nonstop3h 08m
Deal found 10/21![United Airlines logo]()
$587
Best flights from Aspen to ChicagoDiscover 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 October 25, 2026.
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 October 25, 2026.
This American Airlines deal was found by Cheapflights users on 10/21. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/281:07 pm -
Nonstop3h 15m
Sun 1/319:40 am -
Nonstop3h 57m
Deal found 10/21![American Airlines logo]()
$433
This United Airlines deal was found by Cheapflights users on 10/20. 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.
Sun 11/153:18 pm -
1 stop6h 28m
Sun 11/227:00 am -
1 stop4h 42m
Deal found 10/20![United Airlines logo]()
$496
This Delta deal was found by Cheapflights users on 10/25. 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 11/57:30 am -
1 stop8h 28m
Sun 11/85:27 am -
1 stop6h 57m
Deal found 10/25![Delta logo]()
$529
This United Airlines deal was found by Cheapflights users on 10/22. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/113:18 pm -
1 stop6h 28m
Sun 11/157:00 am -
1 stop4h 42m
Deal found 10/22![United Airlines logo]()
$529
This Delta deal was found by Cheapflights users on 10/25. 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 11/67:30 am -
1 stop8h 28m
Sun 11/85:27 am -
1 stop6h 57m
Deal found 10/25![Delta logo]()
$529
This Delta deal was found by Cheapflights users on 10/25. 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 11/47:30 am -
1 stop9h 17m
Sun 11/85:27 am -
1 stop6h 57m
Deal found 10/25![Delta logo]()
$529
This United Airlines deal was found by Cheapflights users on 10/24. 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 11/133:18 pm -
1 stop6h 28m
Mon 11/168:40 am -
1 stop5h 08m
Deal found 10/24![United Airlines logo]()
$529
Last-minute flights from Aspen to ChicagoDiscover last-minute flight deals from Aspen to Chicago. Data last updated October 25, 2026 and is based on user searches.
Discover last-minute flight deals from Aspen to Chicago. Data last updated October 25, 2026 and is based on user searches.
This United Airlines deal was found by Cheapflights users on 10/21. 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.
Thu 10/228:21 am -
Nonstop3h 08m
Thu 10/227:50 pm -
Nonstop3h 08m
Deal found 10/21![United Airlines logo]()
$587
This American Airlines deal was found by Cheapflights users on 10/23. 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.
Tue 10/2712:48 pm -
Nonstop3h 17m
Sun 11/13:00 pm -
1 stop6h 17m
Deal found 10/23![American Airlines logo]()
$519
This Delta deal was found by Cheapflights users on 10/21. 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.
Thu 11/57:30 am -
2 stops12h 00m
Sun 11/85:27 am -
1 stop6h 57m
Deal found 10/21![Delta logo]()
$534
This United Airlines deal was found by Cheapflights users on 10/22. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/61:30 pm -
1 stop5h 59m
Tue 11/1010:55 am -
1 stop4h 42m
Deal found 10/22![United Airlines logo]()
$529
This Delta deal was found by Cheapflights users on 10/22. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/67:30 am -
2 stops12h 00m
Tue 11/105:30 am -
1 stop7h 13m
Deal found 10/22![Delta logo]()
$554
This United Airlines deal was found by Cheapflights users on 10/22. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/71:30 pm -
1 stop5h 01m
Sun 11/87:00 am -
1 stop4h 42m
Deal found 10/22![United Airlines logo]()
$564
This Delta deal was found by Cheapflights users on 10/22. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/77:30 am -
1 stop8h 28m
Mon 11/95:30 am -
1 stop7h 13m
Deal found 10/22![Delta logo]()
$584
This United Airlines deal was found by Cheapflights users on 10/22. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/711:54 am -
Nonstop3h 06m
Mon 11/97:00 am -
1 stop7h 36m
Deal found 10/22![United Airlines logo]()
$594
This United Airlines deal was found by Cheapflights users on 10/22. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/1011:23 am -
1 stop7h 42m
Sat 11/148:47 am -
Nonstop3h 26m
Deal found 10/22![United Airlines logo]()
$524
This United Airlines deal was found by Cheapflights users on 10/20. 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.
Sun 11/153:18 pm -
1 stop6h 28m
Sun 11/227:00 am -
1 stop4h 42m
Deal found 10/20![United Airlines logo]()
$496
This United Airlines deal was found by Cheapflights users on 10/20. 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.
Mon 11/306:09 pm -
1 stop4h 50m
Fri 12/44:15 pm -
Nonstop3h 22m
Deal found 10/20![United Airlines logo]()
$585
One-way flights from Aspen to ChicagoSearch for one-way flight options from Aspen to Chicago. Find affordable one-way fares based on user searches. Data last updated October 25, 2026.
Search for one-way flight options from Aspen to Chicago. Find affordable one-way fares based on user searches. Data last updated October 25, 2026.
This American Airlines deal was found by Cheapflights users on 10/20. 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.
Tue 2/93:10 pm -
Nonstop3h 17m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/20![American Airlines logo]()
$217
This American Airlines deal was found by Cheapflights users on 10/25. 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.
Tue 11/2412:57 pm -
1 stop8h 28m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/25![American Airlines logo]()
$227
This American Airlines deal was found by Cheapflights users on 10/24. 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 10/3012:48 pm -
Nonstop3h 17m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/24![American Airlines logo]()
$255
This United Airlines deal was found by Cheapflights users on 10/25. 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 10/303:18 pm -
1 stop5h 12m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/25![United Airlines logo]()
$265
This Delta deal was found by Cheapflights users on 10/23. 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 11/57:30 am -
2 stops12h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/23![Delta logo]()
$280
This United Airlines deal was found by Cheapflights users on 10/23. 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.
Sun 12/2010:35 am -
Nonstop3h 02m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/23![United Airlines logo]()
$288
This American Airlines deal was found by Cheapflights users on 10/21. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/137:30 am -
1 stop7h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/21![American Airlines logo]()
$298
This United Airlines deal was found by Cheapflights users on 10/21. 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.
Sun 12/1312:45 pm -
Nonstop3h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/21![United Airlines logo]()
$343
This Delta deal was found by Cheapflights users on 10/24. 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 11/132:22 pm -
2 stops17h 42m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/24![Delta logo]()
$355
This American Airlines deal was found by Cheapflights users on 10/24. 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.
Sat 11/147:30 am -
2 stops13h 21m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/24![American Airlines logo]()
$379
This American Airlines deal was found by Cheapflights users on 10/25. 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.
Wed 11/1812:54 pm -
2 stops16h 16m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/25![American Airlines logo]()
$386
This United Airlines deal was found by Cheapflights users on 10/24. 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.
Sat 11/1411:54 am -
Nonstop3h 06m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/24![United Airlines logo]()
$388
Find 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 October 25, 2026.
Most accurate provider | eDreams 2 stars |
|---|---|
Most trusted provider | eDreams 3 stars |
Round-trip from | $433 (American Airlines) |
One-way from | $217 (American Airlines) |
Good round-trip deal | $511 or less |
Good one-way deal | $298 or less |
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 7,457,451 searches. Data last updated October 25, 2026.
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
Cheapest round-trip
Quickest round-trip
AspenChicago
ASE Aspen Pitkin County - ORD Chicago O'Hare Intl
ASEORD
Aspen Pitkin County
Tue 2/9
3:10 pm-7:27 pm
Nonstop3h 17m
Chicago O'Hare Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$217
AspenChicago
ASE Aspen Pitkin County - ORD Chicago O'Hare Intl
ASEORD
Aspen Pitkin County
Tue 2/9
1:00 pm-8:01 pm
1 stop6h 01m
Chicago O'Hare Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$227
AspenChicago
ASE Aspen Pitkin County - ORD Chicago O'Hare Intl
ASEORD
Aspen Pitkin County
Tue 11/24
12:57 pm-10:25 pm
1 stop8h 28m
Chicago O'Hare Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$227
AspenChicago
ASE Aspen Pitkin County - ORD Chicago O'Hare Intl
ASEORD
Aspen Pitkin County
Thu 3/4
8:30 am-2:52 pm
1 stop5h 22m
Chicago O'Hare Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$227
AspenChicago
ASE Aspen Pitkin County - ORD Chicago O'Hare Intl
ASEORD
Aspen Pitkin County
Fri 10/30
12:48 pm-5:05 pm
Nonstop3h 17m
Chicago O'Hare Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$255
AspenChicago
ASE Aspen Pitkin County - ORD Chicago O'Hare Intl
ASEORD
Aspen Pitkin County
Wed 11/11
2:22 pm-11:54 pm
1 stop8h 32m
Chicago O'Hare Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$265
AspenChicago
ASE Aspen Pitkin County - ORD Chicago O'Hare Intl
ASEORD
Aspen Pitkin County
Fri 10/30
3:18 pm-9:30 pm
1 stop5h 12m
Chicago O'Hare Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$265
AspenChicago
ASE Aspen Pitkin County - ORD Chicago O'Hare Intl
ASEORD
Aspen Pitkin County
Thu 11/5
6:09 pm-11:59 pm
1 stop4h 50m
Chicago O'Hare Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$265
AspenChicago
ASE Aspen Pitkin County - ORD Chicago O'Hare Intl
ASEORD
Aspen Pitkin County
Thu 11/5
7:30 am-8:30 pm
2 stops12h 00m
Chicago O'Hare Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$280
AspenChicago
ASE Aspen Pitkin County - ORD Chicago O'Hare Intl
ASEORD
Aspen Pitkin County
Fri 11/6
7:30 am-8:30 pm
2 stops12h 00m
Chicago O'Hare Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$280
Showing 1-10 of 18 resultsSorted by cheapest first
- 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 90-95% 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.
ASE-CHI
ASE-ORD
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
ASE-CHI
ASE-ORD
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 October 25, 2026.
When flying from Aspen to Chicago, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.
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 October 25, 2026.
The most flights from ASE to CHI are scheduled on a Friday (5 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (2 on average).
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 October 25, 2026.
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.
Comfort
7.3
Crew
8.1
Food
6.7
Entertainment
7.1
Boarding
7.7
Overall
7.3
Reviews
1 / 20
4.0
OkayChris,Aug 2026
MIA - ORD
Comfort
7.3
Crew
8.1
Food
6.7
Entertainment
7.1
Boarding
7.7
Overall
7.3
Reviews
1 / 20
4.0
OkayChris,Aug 2026
MIA - ORD
Comfort
7.3
Crew
8.1
Food
6.7
Entertainment
7.1
Boarding
7.7
Overall
7.3
Reviews
1 / 20
4.0
OkayChris,Aug 2026
MIA - ORD
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.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsBenton Harbor
Merrillville
Lansing
Valparaiso
Hammond
Saint Joseph
Porter
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Alternative routes for Aspen to Chicago
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Other flights to Chicago
Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on October 25, 2026.
Complete your trip
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Aspen and Chicago flights
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Other flights from Aspen
Browse through other flights departing from Aspen. Flights are based on user searches made on Cheapflights and were last updated on October 25, 2026.
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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 7,457,451 searches. Data last updated October 25, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$229 | Average$414 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$376 | Average$604 | FlexibilityNo cancel fee | On-time69% |