$217+ Cheap flights from Chicago (CHI) to Aspen (ASE)
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 12/22. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — ASE
Nov 22 — Nov 291
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to Aspen 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.Cheapflights Tip: The best prices from Chicago to Aspen Pitkin County are usually found in August or March, booked 69 days in advance, depart on a Sunday or Tuesday and return on a Friday
Cheap flight deals from Chicago to Aspen
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Cheapest flights from Chicago to AspenExplore the most affordable flight options available from Chicago to Aspen. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 23, 2026.
Explore the most affordable flight options available from Chicago to Aspen. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 23, 2026.
This United Airlines deal was found by Cheapflights users on 10/19. 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.
Sun 12/64:15 pm -
Nonstop3h 22m
Tue 12/1512:45 pm -
Nonstop3h 00m
Deal found 10/19![United Airlines logo]()
$433
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.
Sun 12/65:30 am -
1 stop7h 11m
Tue 12/152:30 pm -
1 stop8h 26m
Deal found 10/21![Delta logo]()
$453
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 12/239:40 am -
Nonstop3h 38m
Tue 12/298:15 am -
Nonstop3h 08m
Deal found 10/22![United Airlines logo]()
$476
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 11/174:20 pm -
1 stop5h 13m
Tue 11/241:30 pm -
1 stop5h 59m
Deal found 10/20![United Airlines logo]()
$491
This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/235:00 am -
1 stop7h 04m
Tue 12/291:04 pm -
1 stop5h 55m
Deal found 10/22![American Airlines logo]()
$496
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 10/2510:00 am -
Nonstop3h 16m
Fri 10/3012:48 pm -
Nonstop3h 17m
Deal found 10/21![American Airlines logo]()
$509
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/176:00 am -
1 stop6h 43m
Tue 11/242:22 pm -
1 stop7h 32m
Deal found 10/20![Delta logo]()
$511
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.
Sat 12/194:15 pm -
Nonstop3h 31m
Wed 12/2311:07 am -
1 stop4h 58m
Deal found 10/21![United Airlines logo]()
$511
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.
Fri 11/136:00 am -
1 stop6h 43m
Sun 11/152:22 pm -
1 stop7h 32m
Deal found 10/21![Delta logo]()
$539
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.
Tue 10/276:04 am -
1 stop6h 17m
Tue 11/102:22 pm -
1 stop7h 32m
Deal found 10/22![Delta logo]()
$549
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.
Thu 11/126:00 am -
1 stop6h 43m
Sun 11/152:22 pm -
1 stop7h 32m
Deal found 10/22![Delta logo]()
$559
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.
Sat 11/76:04 am -
1 stop6h 20m
Tue 11/102:22 pm -
1 stop7h 32m
Deal found 10/21![Delta logo]()
$564
Best flights from Chicago to AspenDiscover carefully curated flight deals from Chicago to Aspen that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 23, 2026.
Discover carefully curated flight deals from Chicago to Aspen that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 23, 2026.
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.
Sun 12/65:30 am -
1 stop7h 11m
Tue 12/152:30 pm -
1 stop8h 26m
Deal found 10/21![Delta logo]()
$453
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.
Thu 11/197:00 am -
1 stop4h 42m
Thu 11/268:45 am -
1 stop7h 19m
Deal found 10/20![United Airlines logo]()
$496
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/176:00 am -
1 stop6h 43m
Tue 11/242:22 pm -
1 stop7h 32m
Deal found 10/20![Delta logo]()
$511
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.
Sun 12/64:15 pm -
Nonstop3h 22m
Tue 12/1512:45 pm -
Nonstop3h 00m
Deal found 10/22![United Airlines logo]()
$544
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.
Fri 11/136:00 am -
1 stop6h 43m
Sun 11/152:22 pm -
1 stop7h 32m
Deal found 10/21![Delta logo]()
$539
This United Airlines deal was found by Cheapflights users on 10/18. 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.
Thu 12/1012:29 pm -
1 stop5h 03m
Sun 12/137:35 am -
1 stop4h 40m
Deal found 10/18![United Airlines logo]()
$581
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.
Sat 11/76:04 am -
1 stop6h 20m
Tue 11/102:22 pm -
1 stop7h 32m
Deal found 10/21![Delta logo]()
$564
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.
Sat 1/169:15 am -
Nonstop3h 38m
Tue 1/193:31 pm -
1 stop7h 27m
Deal found 10/21![United Airlines logo]()
$596
This Delta deal was found by Cheapflights users on 10/19. 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.
Tue 11/36:04 am -
1 stop6h 20m
Sat 11/77:30 am -
1 stop6h 47m
Deal found 10/19![Delta logo]()
$564
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/56:04 am -
1 stop6h 20m
Mon 11/92:22 pm -
1 stop7h 32m
Deal found 10/20![Delta logo]()
$599
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.
Thu 10/296:04 am -
1 stop6h 17m
Sun 11/17:30 am -
1 stop6h 47m
Deal found 10/22![Delta logo]()
$837
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/256:00 am -
1 stop6h 43m
Mon 11/302:22 pm -
1 stop7h 32m
Deal found 10/20![Delta logo]()
$1,307
This Delta deal was found by Cheapflights users on 10/18. 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 11/246:00 am -
1 stop6h 43m
Sat 11/282:22 pm -
1 stop7h 32m
Deal found 10/18![Delta logo]()
$1,319
This Delta deal was found by Cheapflights users on 10/19. 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.
Mon 11/236:00 am -
1 stop6h 43m
Sat 11/282:22 pm -
1 stop7h 32m
Deal found 10/19![Delta logo]()
$1,537
This Delta deal was found by Cheapflights users on 10/18. 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 11/246:00 am -
1 stop6h 43m
Sun 11/292:22 pm -
1 stop7h 32m
Deal found 10/18![Delta logo]()
$1,597
Last-minute flights from Chicago to AspenDiscover last-minute flight deals from Chicago to Aspen. Data last updated October 23, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Aspen. Data last updated October 23, 2026 and is based on user searches.
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 10/2510:00 am -
Nonstop3h 16m
Fri 10/3012:48 pm -
Nonstop3h 17m
Deal found 10/21![American Airlines logo]()
$509
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.
Tue 10/276:04 am -
1 stop6h 17m
Tue 11/102:22 pm -
1 stop7h 32m
Deal found 10/22![Delta logo]()
$549
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 10/271:30 pm -
1 stop4h 27m
Mon 11/93:18 pm -
1 stop5h 12m
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.
Mon 11/25:27 am -
1 stop6h 57m
Fri 11/67:30 am -
2 stops12h 00m
Deal found 10/22![Delta logo]()
$554
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.
Sat 11/76:04 am -
1 stop6h 20m
Tue 11/102:22 pm -
1 stop7h 32m
Deal found 10/21![Delta 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.
Thu 11/126:00 am -
1 stop6h 43m
Sun 11/152:22 pm -
1 stop7h 32m
Deal found 10/22![Delta logo]()
$559
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.
Fri 11/136:00 am -
1 stop6h 43m
Sun 11/152:22 pm -
1 stop7h 32m
Deal found 10/21![Delta logo]()
$539
This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/131:44 pm -
1 stop7h 33m
Sun 11/1512:54 pm -
1 stop8h 36m
Deal found 10/22![American Airlines logo]()
$539
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 11/174:20 pm -
1 stop5h 13m
Tue 11/241:30 pm -
1 stop5h 59m
Deal found 10/20![United Airlines logo]()
$491
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/176:00 am -
1 stop6h 43m
Tue 11/242:22 pm -
1 stop7h 32m
Deal found 10/20![Delta logo]()
$511
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.
Thu 11/197:00 am -
1 stop4h 42m
Thu 11/268:45 am -
1 stop7h 19m
Deal found 10/20![United Airlines logo]()
$496
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.
Thu 11/193:03 pm -
1 stop6h 23m
Thu 11/267:25 am -
2 stops23h 00m
Deal found 10/20![American Airlines logo]()
$549
One-way flights from Chicago to AspenSearch for one-way flight options from Chicago to Aspen. Find affordable one-way fares based on user searches. Data last updated October 23, 2026.
Search for one-way flight options from Chicago to Aspen. Find affordable one-way fares based on user searches. Data last updated October 23, 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 12/228:00 am -
Nonstop3h 42m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/20![American Airlines logo]()
$217
This United Airlines deal was found by Cheapflights users on 10/19. 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.
Mon 11/232:30 pm -
1 stop7h 03m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/19![United Airlines logo]()
$227
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 11/15:00 am -
1 stop8h 24m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/21![American Airlines logo]()
$265
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 11/242:30 pm -
1 stop4h 57m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/22![United Airlines logo]()
$267
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.
Sun 11/156:00 am -
1 stop6h 43m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/22![Delta logo]()
$275
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.
Wed 3/311:52 am -
Nonstop3h 51m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/21![American Airlines logo]()
$288
This American Airlines deal was found by Cheapflights users on 10/18. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/165:00 am -
1 stop8h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/18![American Airlines logo]()
$300
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.
Wed 10/286:04 am -
1 stop6h 17m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/21![Delta logo]()
$309
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.
Wed 10/285:27 am -
1 stop6h 54m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/21![Delta logo]()
$309
This Trip.com 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/145:30 am -
1 stop9h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/20![Delta logo]()
$310
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.
Fri 12/1112:59 pm -
1 stop6h 44m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/20![United Airlines logo]()
$313
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.
Wed 10/2810:00 am -
Nonstop3h 16m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/21![American Airlines logo]()
$333
Find flight deals from Chicago to Aspen
Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Aspen (ASE). 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 23, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $433 (United Airlines) |
One-way from | $217 (American Airlines) |
Popular in | January |
Cheapest in | August |
Average price | $559 |
Good round-trip deal | $499 or less |
Good one-way deal | $244 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago to Aspen 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 23, 2026.
Use the filters below to find and compare flights from Chicago to Aspen that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoAspen
ORD Chicago O'Hare Intl - ASE Aspen Pitkin County
ORDASE
Chicago O'Hare Intl
Mon 11/23
2:30 pm-8:33 pm
1 stop7h 03m
Aspen Pitkin County
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$227
ChicagoAspen
ORD Chicago O'Hare Intl - ASE Aspen Pitkin County
ORDASE
Chicago O'Hare Intl
Tue 11/24
7:00 am-10:42 am
1 stop4h 42m
Aspen Pitkin County
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$227
ChicagoAspen
ORD Chicago O'Hare Intl - ASE Aspen Pitkin County
ORDASE
Chicago O'Hare Intl
Sun 11/15
3:00 pm-8:17 pm
1 stop6h 17m
Aspen Pitkin County
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$265
ChicagoAspen
ORD Chicago O'Hare Intl - ASE Aspen Pitkin County
ORDASE
Chicago O'Hare Intl
Sun 11/1
5:00 am-12:24 pm
1 stop8h 24m
Aspen Pitkin County
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$265
ChicagoAspen
ORD Chicago O'Hare Intl - ASE Aspen Pitkin County
ORDASE
Chicago O'Hare Intl
Mon 10/26
10:55 am-4:57 pm
1 stop7h 02m
Aspen Pitkin County
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$265
ChicagoAspen
MDW Chicago Midway - ASE Aspen Pitkin County
MDWASE
Chicago Midway
Sun 11/15
6:00 am-11:43 am
1 stop6h 43m
Aspen Pitkin County
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$275
ChicagoAspen
ORD Chicago O'Hare Intl - ASE Aspen Pitkin County
ORDASE
Chicago O'Hare Intl
Fri 12/18
7:20 am-9:54 am
Nonstop3h 34m
Aspen Pitkin County
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$288
ChicagoAspen
ORD Chicago O'Hare Intl - ASE Aspen Pitkin County
ORDASE
Chicago O'Hare Intl
Wed 12/23
6:50 am-10:57 am
1 stop5h 07m
Aspen Pitkin County
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$298
ChicagoAspen
MDW Chicago Midway - ASE Aspen Pitkin County
MDWASE
Chicago Midway
Wed 10/28
6:04 am-11:21 am
1 stop6h 17m
Aspen Pitkin County
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$309
ChicagoAspen
ORD Chicago O'Hare Intl - ASE Aspen Pitkin County
ORDASE
Chicago O'Hare Intl
Wed 10/28
5:27 am-11:21 am
1 stop6h 54m
Aspen Pitkin County
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$309
Showing 1-10 of 33 resultsSorted by cheapest first
Compare providers for flights from Chicago to Aspen
Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Chicago to Aspen in October.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Chicago-Aspen flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-Aspen flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago-Aspen flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Chicago-Aspen 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 Chicago-Aspen 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 Chicago to Aspen
Have a flexible travel schedule? Discover the best time to fly to Aspen from Chicago with our price prediction graph.
CHI-ASE
ORD-ASE
MDW-ASE
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 Chicago to Aspen
CHI-ASE
ORD-ASE
MDW-ASE
What is the cheapest month to book a flight from Chicago to Aspen?
Currently, May is the cheapest month in which you can book a flight from Chicago to Aspen (average of $299). Flying from Chicago to Aspen in October is currently the most expensive (average of $733). 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 CHI to ASE?
Find hourly flight availability from Chicago to Aspen. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated October 23, 2026.
One of the essential ways to save on airfare from Chicago to Aspen is to remain as flexible as possible. Flights that are in the evening tend to be the most expensive. A flight in the afternoon could potentially save you up to 28% on airfare.
Weekly flight availability from Chicago to Aspen
Explore weekly flight availability from Chicago to Aspen. 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 23, 2026.
The most flights from CHI to ASE are scheduled on a Wednesday (4 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (1 on average).
How far ahead should I book a flight from Chicago to Aspen?
To ensure you get the cheapest price possible for a flight from Chicago to Aspen, you should look to book at least 62 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.
Reviews of airlines servicing Aspen
Get insights into the airlines that provide service to Aspen. 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 Aspen. Reviews last updated October 23, 2026.
Read reviews from past customers who have flown United Airlines and American Airlines from Chicago to Aspen. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Entertainment
7.1
Boarding
7.7
Food
6.7
Crew
8.1
Comfort
7.3
Overall
7.3
Reviews
1 / 20
2.0
MediocreDawn,Aug 2026
ORD - DEN
Entertainment
7.1
Boarding
7.7
Food
6.7
Crew
8.1
Comfort
7.3
Overall
7.3
Reviews
1 / 20
2.0
MediocreDawn,Aug 2026
ORD - DEN
Entertainment
7.1
Boarding
7.7
Food
6.7
Crew
8.1
Comfort
7.3
Overall
7.3
Reviews
1 / 20
2.0
MediocreDawn,Aug 2026
ORD - DEN
Related info for your journey
Find useful and relevant information for your journey from Chicago to Aspen. 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 Aspen?
Book flights to Aspen if you plan to visit one of these locationsSnowmass Village
Leadville
Snowmass
Browse thousands of different options on Cheapflights for your next trip
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Other flights to Aspen
Explore flights to Aspen departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on October 23, 2026.
Complete your trip
Complete your trip to Aspen by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Chicago to Aspen by cabin class
Find flights from Chicago to Aspen, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Chicago and Aspen flights
Browse other Chicago and Aspen flight options. Last updated on October 23, 2026.
Other flights from Chicago
Browse through other flights departing from Chicago. Flights are based on user searches made on Cheapflights and were last updated on October 23, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 2 airlines flying from Chicago to Aspen
Discover the top 2 airlines that operate flights from Chicago to Aspen. 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 23, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$328 | Average$499 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$356 | Average$552 | FlexibilityNo cancel fee | On-time69% |