$197+ 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 12/9. Fares are subject to change and may not be available on all flights or dates of travel.
ASE — CHI
Oct 14 — Oct 211
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 September 14, 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 September 14, 2026.
This American Airlines deal was found by Cheapflights users on 9/13. 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 10/1512:48 pm -
Nonstop3h 17m
Mon 10/1910:00 am -
Nonstop3h 16m
Deal found 9/13![American Airlines logo]()
$413
This United Airlines deal was found by Cheapflights users on 9/13. 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 10/156:05 pm -
1 stop4h 54m
Mon 10/197:50 pm -
Nonstop3h 08m
Deal found 9/13![United Airlines logo]()
$423
This United Airlines deal was found by Cheapflights users on 9/9. 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 11/243:18 pm -
1 stop7h 41m
Tue 12/14:10 pm -
Nonstop3h 06m
Deal found 9/9![United Airlines logo]()
$425
This American Airlines deal was found by Cheapflights users on 9/9. 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 10/812:48 pm -
Nonstop3h 17m
Mon 10/1210:00 am -
Nonstop3h 16m
Deal found 9/9![American Airlines logo]()
$431
This American Airlines deal was found by Cheapflights users on 9/10. 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 10/77:30 am -
1 stop7h 46m
Sun 10/1110:00 am -
Nonstop3h 16m
Deal found 9/10![American Airlines logo]()
$441
This United Airlines deal was found by Cheapflights users on 9/9. 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 10/86:05 pm -
1 stop4h 54m
Mon 10/129:10 am -
Nonstop3h 19m
Deal found 9/9![United Airlines logo]()
$452
This United Airlines deal was found by Cheapflights users on 9/9. 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 9/178:21 am -
Nonstop3h 08m
Mon 9/217:47 pm -
Nonstop3h 08m
Deal found 9/9![United Airlines logo]()
$469
This Delta deal was found by Cheapflights users on 9/12. 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 9/187:35 am -
1 stop7h 40m
Sun 9/206:05 am -
1 stop6h 16m
Deal found 9/12![Delta logo]()
$573
This Delta deal was found by Cheapflights users on 9/11. 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 9/267:35 am -
1 stop6h 49m
Wed 9/306:05 am -
1 stop6h 16m
Deal found 9/11![Delta logo]()
$579
This Delta deal was found by Cheapflights users on 9/14. 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 9/197:35 am -
1 stop6h 49m
Sun 9/206:05 am -
1 stop6h 16m
Deal found 9/14![Delta logo]()
$651
This Delta deal was found by Cheapflights users on 9/9. 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 9/177:35 am -
1 stop7h 40m
Mon 9/216:05 am -
1 stop6h 16m
Deal found 9/9![Delta logo]()
$769
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 September 14, 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 September 14, 2026.
This United Airlines deal was found by Cheapflights users on 9/9. 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 11/243:18 pm -
1 stop7h 41m
Tue 12/14:10 pm -
Nonstop3h 06m
Deal found 9/9![United Airlines logo]()
$425
This American Airlines deal was found by Cheapflights users on 9/10. 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 10/77:30 am -
1 stop6h 49m
Sun 10/116:00 am -
1 stop7h 26m
Deal found 9/10![American Airlines logo]()
$451
This Delta deal was found by Cheapflights users on 9/11. 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 9/267:35 am -
1 stop6h 49m
Wed 9/306:05 am -
1 stop6h 16m
Deal found 9/11![Delta logo]()
$579
This United Airlines deal was found by Cheapflights users on 9/13. 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 10/156:05 pm -
1 stop4h 54m
Mon 10/194:20 pm -
1 stop5h 01m
Deal found 9/13![United Airlines logo]()
$433
This United Airlines deal was found by Cheapflights users on 9/12. 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 10/96:05 pm -
1 stop4h 54m
Mon 10/127:50 pm -
Nonstop3h 08m
Deal found 9/12![United Airlines logo]()
$461
This Delta deal was found by Cheapflights users on 9/11. 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 9/267:35 am -
2 stops11h 55m
Wed 9/305:30 am -
1 stop6h 51m
Deal found 9/11![Delta logo]()
$584
This United Airlines deal was found by Cheapflights users on 9/11. 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 9/268:21 am -
Nonstop3h 08m
Wed 9/307:50 pm -
Nonstop3h 08m
Deal found 9/11![United Airlines logo]()
$539
This United Airlines deal was found by Cheapflights users on 9/10. 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
Mon 10/265:59 am -
1 stop8h 37m
Deal found 9/10![United Airlines logo]()
$566
This Delta deal was found by Cheapflights users on 9/12. 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.
Sun 9/277:35 am -
1 stop7h 40m
Thu 10/16:05 am -
1 stop6h 16m
Deal found 9/12![Delta logo]()
$1,327
This Delta deal was found by Cheapflights users on 9/12. 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 10/97:30 am -
1 stop7h 44m
Mon 10/126:04 am -
1 stop6h 17m
Deal found 9/12![Delta logo]()
$1,775
This Delta deal was found by Cheapflights users on 9/9. 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 10/87:30 am -
1 stop7h 44m
Mon 10/126:04 am -
1 stop6h 17m
Deal found 9/9![Delta logo]()
$3,296
Last-minute flights from Aspen to ChicagoDiscover last-minute flight deals from Aspen to Chicago. Data last updated September 14, 2026 and is based on user searches.
Discover last-minute flight deals from Aspen to Chicago. Data last updated September 14, 2026 and is based on user searches.
This United Airlines deal was found by Cheapflights users on 9/9. 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 9/178:21 am -
Nonstop3h 08m
Mon 9/217:47 pm -
Nonstop3h 08m
Deal found 9/9![United Airlines logo]()
$469
This Delta deal was found by Cheapflights users on 9/9. 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 9/177:35 am -
1 stop7h 40m
Mon 9/216:05 am -
1 stop6h 16m
Deal found 9/9![Delta logo]()
$769
This Delta deal was found by Cheapflights users on 9/12. 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 9/187:35 am -
1 stop7h 40m
Sun 9/206:05 am -
1 stop6h 16m
Deal found 9/12![Delta logo]()
$573
This Delta deal was found by Cheapflights users on 9/14. 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 9/197:35 am -
1 stop6h 49m
Sun 9/206:05 am -
1 stop6h 16m
Deal found 9/14![Delta logo]()
$651
This Delta deal was found by Cheapflights users on 9/11. 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 9/267:35 am -
1 stop6h 49m
Wed 9/306:05 am -
1 stop6h 16m
Deal found 9/11![Delta logo]()
$579
This American Airlines deal was found by Cheapflights users on 9/10. 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 10/77:30 am -
1 stop7h 46m
Sun 10/1110:00 am -
Nonstop3h 16m
Deal found 9/10![American Airlines logo]()
$441
This American Airlines deal was found by Cheapflights users on 9/9. 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 10/812:48 pm -
Nonstop3h 17m
Mon 10/1210:00 am -
Nonstop3h 16m
Deal found 9/9![American Airlines logo]()
$431
This United Airlines deal was found by Cheapflights users on 9/9. 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 10/86:05 pm -
1 stop4h 54m
Mon 10/129:10 am -
Nonstop3h 19m
Deal found 9/9![United Airlines logo]()
$452
This American Airlines deal was found by Cheapflights users on 9/13. 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 10/1512:48 pm -
Nonstop3h 17m
Mon 10/1910:00 am -
Nonstop3h 16m
Deal found 9/13![American Airlines logo]()
$413
This United Airlines deal was found by Cheapflights users on 9/13. 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 10/156:05 pm -
1 stop4h 54m
Mon 10/197:50 pm -
Nonstop3h 08m
Deal found 9/13![United Airlines logo]()
$423
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 September 14, 2026.
Search for one-way flight options from Aspen to Chicago. Find affordable one-way fares based on user searches. Data last updated September 14, 2026.
This United Airlines deal was found by Cheapflights users on 9/9. 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 12/99:00 am -
Nonstop3h 09m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![United Airlines logo]()
$197
This United Airlines deal was found by Cheapflights users on 9/14. 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 12/109:00 am -
Nonstop3h 09m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/14![United Airlines logo]()
$207
This Delta deal was found by Cheapflights users on 9/11. 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 11/121:52 pm -
1 stop9h 02m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/11![Delta logo]()
$217
This Delta deal was found by Cheapflights users on 9/14. 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 10/147:30 am -
2 stops12h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/14![Delta logo]()
$222
This American Airlines deal was found by Cheapflights users on 9/9. 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 10/812:48 pm -
Nonstop3h 17m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![American Airlines logo]()
$235
This United Airlines deal was found by Cheapflights users on 9/11. 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 12/89:00 am -
Nonstop3h 09m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/11![United Airlines logo]()
$242
This American Airlines deal was found by Cheapflights users on 9/13. 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 9/237:00 am -
Nonstop3h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/13![American Airlines logo]()
$245
This Delta deal was found by Cheapflights users on 9/11. 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.
Tue 3/92:55 pm -
1 stop6h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/11![Delta logo]()
$250
This United Airlines deal was found by Cheapflights users on 9/14. 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 10/1412:15 pm -
Nonstop3h 04m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/14![United Airlines logo]()
$252
This United Airlines deal was found by Cheapflights users on 9/13. 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 9/233:20 pm -
1 stop6h 26m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/13![United Airlines logo]()
$255
This United Airlines deal was found by Cheapflights users on 9/12. 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 10/131:15 pm -
1 stop5h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/12![United Airlines logo]()
$262
This United Airlines deal was found by Cheapflights users on 9/10. 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 10/108:21 am -
Nonstop3h 08m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![United Airlines logo]()
$269
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 September 14, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $413 (American Airlines) |
One-way from | $197 (United Airlines) |
Good round-trip deal | $514 or less |
Good one-way deal | $238 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 September 14, 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
AspenChicago
ASE Aspen Pitkin County - ORD Chicago O'Hare Intl
ASEORD
Aspen Pitkin County
Tue 3/9
1:50 pm-7:43 pm
1 stop4h 53m
Chicago O'Hare Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$207
Quickest round-trip
AspenChicago
ASE Aspen Pitkin County - ORD Chicago O'Hare Intl
ASEORD
Aspen Pitkin County
Wed 12/23
8:15 am-12:23 pm
Nonstop3h 08m
Chicago O'Hare Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$207
AspenChicago
ASE Aspen Pitkin County - ORD Chicago O'Hare Intl
ASEORD
Aspen Pitkin County
Fri 11/13
1:52 pm-11:54 pm
1 stop9h 02m
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
Thu 12/10
1:56 pm-11:52 pm
1 stop8h 56m
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
Wed 10/14
7:30 am-8:30 pm
2 stops12h 00m
Chicago O'Hare Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$222
AspenChicago
ASE Aspen Pitkin County - ORD Chicago O'Hare Intl
ASEORD
Aspen Pitkin County
Thu 12/10
9:00 am-1:09 pm
Nonstop3h 09m
Chicago O'Hare Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$242
AspenChicago
ASE Aspen Pitkin County - ORD Chicago O'Hare Intl
ASEORD
Aspen Pitkin County
Wed 3/10
2:10 pm-6:18 pm
Nonstop3h 08m
Chicago O'Hare Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$242
AspenChicago
ASE Aspen Pitkin County - ORD Chicago O'Hare Intl
ASEORD
Aspen Pitkin County
Wed 12/16
1:56 pm-11:52 pm
1 stop8h 56m
Chicago O'Hare Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$250
AspenChicago
ASE Aspen Pitkin County - ORD Chicago O'Hare Intl
ASEORD
Aspen Pitkin County
Tue 12/8
9:00 am-1:09 pm
Nonstop3h 09m
Chicago O'Hare Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$252
AspenChicago
ASE Aspen Pitkin County - ORD Chicago O'Hare Intl
ASEORD
Aspen Pitkin County
Sat 10/10
7:30 am-4:58 pm
1 stop8h 28m
Chicago O'Hare Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$278
Showing 1-10 of 29 resultsSorted by cheapest first
- 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.
ASE-CHI
ASE-ORD
ASE-MDW
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
ASE-MDW
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 September 14, 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 September 14, 2026.
The most flights from ASE to CHI are scheduled on a Monday (5 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (5 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 September 14, 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.
Crew
8.1
Entertainment
7.1
Food
6.7
Comfort
7.3
Boarding
7.7
Overall
7.4
Reviews
1 / 20
4.0
OkayChris,Aug 2026
MIA - ORD
Crew
8.1
Entertainment
7.1
Food
6.7
Comfort
7.3
Boarding
7.7
Overall
7.4
Reviews
1 / 20
4.0
OkayChris,Aug 2026
MIA - ORD
Crew
8.1
Entertainment
7.1
Food
6.7
Comfort
7.3
Boarding
7.7
Overall
7.4
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
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
Porter
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Aspen and Chicago flights
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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 September 14, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$229 | Average$414 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$369 | Average$449 | FlexibilityNo cancel fee | On-time69% |