$187+ 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 9/15. Fares are subject to change and may not be available on all flights or dates of travel.
ASE — CHI
Sep 18 — Sep 251
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
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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 August 19, 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 August 19, 2026.
This American Airlines deal was found by Cheapflights users on 8/15. 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 9/257:00 am -
Nonstop3h 05m
Sun 10/47:20 pm -
Nonstop3h 09m
Deal found 8/15![American Airlines logo]()
$373
This United Airlines deal was found by Cheapflights users on 8/17. 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 9/253:20 pm -
1 stop4h 58m
Sun 9/277:50 pm -
Nonstop3h 08m
Deal found 8/17![United Airlines logo]()
$383
This American Airlines deal was found by Cheapflights users on 8/17. 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 10/712:48 pm -
Nonstop3h 17m
Sun 10/1110:00 am -
Nonstop3h 16m
Deal found 8/17![American Airlines logo]()
$411
This American Airlines deal was found by Cheapflights users on 8/17. 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 9/197:00 am -
Nonstop3h 05m
Sun 9/207:20 pm -
Nonstop3h 09m
Deal found 8/17![American Airlines logo]()
$436
This American Airlines deal was found by Cheapflights users on 8/16. 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 10/712:48 pm -
Nonstop3h 17m
Fri 10/910:00 am -
Nonstop3h 16m
Deal found 8/16![American Airlines logo]()
$444
This American Airlines deal was found by Cheapflights users on 8/14. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/31:54 pm -
Nonstop3h 13m
Sun 9/611:16 am -
Nonstop3h 08m
Deal found 8/14![American Airlines logo]()
$449
This United Airlines deal was found by Cheapflights users on 8/16. 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 10/78:21 am -
Nonstop3h 08m
Fri 10/92:30 pm -
1 stop4h 58m
Deal found 8/16![United Airlines logo]()
$454
This Delta deal was found by Cheapflights users on 8/14. 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.
Thu 9/37:20 am -
1 stop7h 55m
Sun 9/66:05 am -
1 stop6h 18m
Deal found 8/14![Delta logo]()
$469
This Delta deal was found by Cheapflights users on 8/17. 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 8/197:20 am -
1 stop7h 55m
Sun 8/236:05 am -
1 stop6h 18m
Deal found 8/17![Delta logo]()
$533
This Delta deal was found by Cheapflights users on 8/19. 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 9/307:35 am -
2 stops9h 58m
Mon 10/56:05 am -
1 stop6h 16m
Deal found 8/19![Delta logo]()
$641
This Delta deal was found by Cheapflights users on 8/18. 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 9/157:35 am -
1 stop7h 40m
Tue 9/226:05 am -
1 stop6h 16m
Deal found 8/18![Delta logo]()
$716
This Delta deal was found by Cheapflights users on 8/19. 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 9/37:20 am -
1 stop7h 55m
Mon 9/76:05 am -
1 stop6h 18m
Deal found 8/19![Delta logo]()
$723
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 August 19, 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 August 19, 2026.
This United Airlines deal was found by Cheapflights users on 8/16. 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 9/154:45 pm -
1 stop5h 01m
Tue 9/297:50 pm -
Nonstop3h 08m
Deal found 8/16![United Airlines logo]()
$383
This American Airlines deal was found by Cheapflights users on 8/19. 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 10/712:56 pm -
1 stop8h 14m
Sun 10/116:55 am -
1 stop6h 31m
Deal found 8/19![American Airlines logo]()
$431
This Delta deal was found by Cheapflights users on 8/14. 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.
Thu 9/37:20 am -
1 stop7h 55m
Sun 9/66:05 am -
1 stop6h 18m
Deal found 8/14![Delta logo]()
$469
This United Airlines deal was found by Cheapflights users on 8/16. 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 10/78:21 am -
Nonstop3h 08m
Fri 10/92:30 pm -
1 stop4h 58m
Deal found 8/16![United Airlines logo]()
$454
This United Airlines deal was found by Cheapflights users on 8/19. 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 9/84:45 pm -
1 stop5h 01m
Sun 9/139:00 am -
Nonstop3h 10m
Deal found 8/19![United Airlines logo]()
$459
This United Airlines deal was found by Cheapflights users on 8/15. 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 10/2312:15 pm -
Nonstop3h 04m
Tue 10/277:00 am -
1 stop6h 48m
Deal found 8/15![United Airlines logo]()
$473
This Delta deal was found by Cheapflights users on 8/19. 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 9/307:35 am -
2 stops9h 58m
Mon 10/56:05 am -
1 stop6h 16m
Deal found 8/19![Delta logo]()
$641
This Delta deal was found by Cheapflights users on 8/18. 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 9/157:35 am -
1 stop7h 40m
Tue 9/226:05 am -
1 stop6h 16m
Deal found 8/18![Delta logo]()
$716
This Delta deal was found by Cheapflights users on 8/16. 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 9/157:35 am -
2 stops9h 58m
Tue 9/296:05 am -
1 stop6h 16m
Deal found 8/16![Delta logo]()
$811
This Delta deal was found by Cheapflights users on 8/17. 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 9/17:20 am -
1 stop7h 24m
Sat 9/56:05 am -
1 stop6h 18m
Deal found 8/17![Delta logo]()
$839
This Delta deal was found by Cheapflights users on 8/18. 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 8/18![Delta logo]()
$916
This Delta deal was found by Cheapflights users on 8/15. 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 9/257:35 am -
1 stop7h 40m
Sun 10/46:05 am -
1 stop6h 16m
Deal found 8/15![Delta logo]()
$967
This Delta deal was found by Cheapflights users on 8/19. 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 9/37:20 am -
2 stops10h 13m
Mon 9/76:05 am -
1 stop6h 18m
Deal found 8/19![Delta logo]()
$1,074
This Delta deal was found by Cheapflights users on 8/19. 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 10/77:30 am -
1 stop7h 44m
Fri 10/96:04 am -
1 stop6h 17m
Deal found 8/19![Delta logo]()
$1,132
Last-minute flights from Aspen to ChicagoDiscover last-minute flight deals from Aspen to Chicago. Data last updated August 19, 2026 and is based on user searches.
Discover last-minute flight deals from Aspen to Chicago. Data last updated August 19, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 8/16. 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 8/1912:50 pm -
1 stop8h 23m
Sun 8/2311:16 am -
Nonstop3h 08m
Deal found 8/16![American Airlines logo]()
$459
This Delta deal was found by Cheapflights users on 8/17. 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 8/197:20 am -
1 stop7h 55m
Sun 8/236:05 am -
1 stop6h 18m
Deal found 8/17![Delta logo]()
$533
This American Airlines deal was found by Cheapflights users on 8/17. 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 8/281:54 pm -
Nonstop3h 13m
Sun 10/47:20 pm -
Nonstop3h 09m
Deal found 8/17![American Airlines logo]()
$411
This United Airlines deal was found by Cheapflights users on 8/17. 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 8/286:05 pm -
1 stop4h 54m
Sun 10/45:00 am -
1 stop4h 59m
Deal found 8/17![United Airlines logo]()
$431
This American Airlines deal was found by Cheapflights users on 8/14. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/31:54 pm -
Nonstop3h 13m
Sun 9/611:16 am -
Nonstop3h 08m
Deal found 8/14![American Airlines logo]()
$449
This Delta deal was found by Cheapflights users on 8/14. 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.
Thu 9/37:20 am -
1 stop7h 55m
Sun 9/66:05 am -
1 stop6h 18m
Deal found 8/14![Delta logo]()
$469
This Delta deal was found by Cheapflights users on 8/19. 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 9/37:20 am -
1 stop7h 55m
Mon 9/76:05 am -
1 stop6h 18m
Deal found 8/19![Delta logo]()
$723
This Delta deal was found by Cheapflights users on 8/18. 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 9/157:35 am -
1 stop7h 40m
Tue 9/226:05 am -
1 stop6h 16m
Deal found 8/18![Delta logo]()
$716
This American Airlines deal was found by Cheapflights users on 8/17. 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 9/197:00 am -
Nonstop3h 05m
Sun 9/207:20 pm -
Nonstop3h 09m
Deal found 8/17![American Airlines logo]()
$436
This American Airlines deal was found by Cheapflights users on 8/15. 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 9/257:00 am -
Nonstop3h 05m
Sun 10/47:20 pm -
Nonstop3h 09m
Deal found 8/15![American Airlines logo]()
$373
This United Airlines deal was found by Cheapflights users on 8/17. 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 9/253:20 pm -
1 stop4h 58m
Sun 9/277:50 pm -
Nonstop3h 08m
Deal found 8/17![United Airlines logo]()
$383
This Delta deal was found by Cheapflights users on 8/19. 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 9/307:35 am -
2 stops9h 58m
Mon 10/56:05 am -
1 stop6h 16m
Deal found 8/19![Delta logo]()
$641
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 August 19, 2026.
Search for one-way flight options from Aspen to Chicago. Find affordable one-way fares based on user searches. Data last updated August 19, 2026.
This American Airlines deal was found by Cheapflights users on 8/16. 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 9/157:00 am -
Nonstop3h 05m
Deal found 8/16![American Airlines logo]()
$187
This United Airlines deal was found by Cheapflights users on 8/16. 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 9/151:15 pm -
1 stop6h 07m
Deal found 8/16![United Airlines logo]()
$197
This Delta deal was found by Cheapflights users on 8/18. 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 11/37:30 am -
1 stop6h 47m
Deal found 8/18![Delta logo]()
$212
This Delta deal was found by Cheapflights users on 8/17. 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 11/171:52 pm -
1 stop9h 07m
Deal found 8/17![Delta logo]()
$212
This Delta deal was found by Cheapflights users on 8/15. 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
Deal found 8/15![Delta logo]()
$217
This American Airlines deal was found by Cheapflights users on 8/16. 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 9/41:54 pm -
Nonstop3h 13m
Deal found 8/16![American Airlines logo]()
$225
This Delta deal was found by Cheapflights users on 8/18. 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 stop6h 47m
Deal found 8/18![Delta logo]()
$230
This Delta deal was found by Cheapflights users on 8/19. 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 10/167:30 am -
1 stop8h 28m
Deal found 8/19![Delta logo]()
$230
This American Airlines deal was found by Cheapflights users on 8/17. 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
Deal found 8/17![American Airlines logo]()
$232
This Delta deal was found by Cheapflights users on 8/15. 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 9/47:20 am -
1 stop7h 55m
Deal found 8/15![Delta logo]()
$235
This Delta deal was found by Cheapflights users on 8/19. 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 9/167:35 am -
2 stops11h 55m
Deal found 8/19![Delta logo]()
$240
This United Airlines deal was found by Cheapflights users on 8/18. 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 9/184:45 pm -
1 stop6h 14m
Deal found 8/18![United Airlines logo]()
$242
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 August 19, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $373 (American Airlines) |
One-way from | $187 (American Airlines) |
Good round-trip deal | $504 or less |
Good one-way deal | $299 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 August 19, 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 9/15
4:45 pm-10:46 pm
1 stop5h 01m
Chicago O'Hare Intl
Tue 9/29
7:50 pm-9:58 pm
Nonstop3h 08m
$383
AspenChicago
ASE Aspen Pitkin County - ORD Chicago O'Hare Intl
ASEORD
Aspen Pitkin County
Wed 10/7
12:56 pm-10:10 pm
1 stop8h 14m
Chicago O'Hare Intl
Sun 10/11
6:55 am-12:26 pm
1 stop6h 31m
$431
Quickest round-trip
AspenChicago
ASE Aspen Pitkin County - ORD Chicago O'Hare Intl
ASEORD
Aspen Pitkin County
Wed 10/7
8:21 am-12:29 pm
Nonstop3h 08m
Chicago O'Hare Intl
Fri 10/9
2:30 pm-6:28 pm
1 stop4h 58m
$454
AspenChicago
ASE Aspen Pitkin County - ORD Chicago O'Hare Intl
ASEORD
Aspen Pitkin County
Tue 9/8
4:45 pm-10:46 pm
1 stop5h 01m
Chicago O'Hare Intl
Sun 9/13
9:00 am-11:10 am
Nonstop3h 10m
$459
AspenChicago
ASE Aspen Pitkin County - MDW Chicago Midway
ASEMDW
Aspen Pitkin County
Thu 9/3
7:20 am-4:15 pm
1 stop7h 55m
Chicago Midway
Sun 9/6
6:05 am-11:23 am
1 stop6h 18m
$469
AspenChicago
ASE Aspen Pitkin County - ORD Chicago O'Hare Intl
ASEORD
Aspen Pitkin County
Fri 10/23
12:15 pm-4:19 pm
Nonstop3h 04m
Chicago O'Hare Intl
Tue 10/27
7:00 am-12:48 pm
1 stop6h 48m
$473
AspenChicago
ASE Aspen Pitkin County - MDW Chicago Midway
ASEMDW
Aspen Pitkin County
Wed 9/30
7:35 am-6:33 pm
2 stops9h 58m
Chicago Midway
Mon 10/5
6:05 am-11:21 am
1 stop6h 16m
$641
AspenChicago
ASE Aspen Pitkin County - MDW Chicago Midway
ASEMDW
Aspen Pitkin County
Tue 9/15
7:35 am-4:15 pm
1 stop7h 40m
Chicago Midway
Tue 9/22
6:05 am-11:21 am
1 stop6h 16m
$716
AspenChicago
ASE Aspen Pitkin County - MDW Chicago Midway
ASEMDW
Aspen Pitkin County
Tue 9/15
7:35 am-6:33 pm
2 stops9h 58m
Chicago Midway
Tue 9/29
6:05 am-11:21 am
1 stop6h 16m
$811
AspenChicago
ASE Aspen Pitkin County - MDW Chicago Midway
ASEMDW
Aspen Pitkin County
Tue 9/1
7:20 am-3:44 pm
1 stop7h 24m
Chicago Midway
Sat 9/5
6:05 am-11:23 am
1 stop6h 18m
$839
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 August 19, 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 August 19, 2026.
The most flights from ASE to CHI are scheduled on a Monday (6 on average). You will have fewer flight options on Wednesday, 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 August 19, 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
Boarding
7.7
Food
6.7
Comfort
7.3
Overall
7.4
Entertainment
7.1
Reviews
1 / 20
4.0
OkayChris,Aug 2026
MIA - ORD
Crew
8.1
Boarding
7.7
Food
6.7
Comfort
7.3
Overall
7.4
Entertainment
7.1
Reviews
1 / 20
4.0
OkayChris,Aug 2026
MIA - ORD
Crew
8.1
Boarding
7.7
Food
6.7
Comfort
7.3
Overall
7.4
Entertainment
7.1
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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Other flights to Chicago
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Aspen and Chicago flights
Browse other Aspen and Chicago flight options. Last updated on August 19, 2026.
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 August 19, 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 August 19, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$335 | Average$449 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$343 | Average$414 | FlexibilityNo cancel fee | On-time71% |