$197+ 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 10/4. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — ASE
Oct 6 — Oct 131
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 Tuesday or Sunday and return on a Thursday
Cheap flight deals from Chicago to Aspen
Cheapest
Best
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One-way
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 September 6, 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 September 6, 2026.
This United Airlines deal was found by Cheapflights users on 9/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/207:20 am -
Nonstop3h 34m
Wed 12/2312:47 pm -
Nonstop3h 03m
Deal found 9/2![United Airlines logo]()
$393
This United Airlines deal was found by Cheapflights users on 9/1. 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 10/109:10 am -
Nonstop3h 19m
Wed 10/1412:15 pm -
Nonstop3h 04m
Deal found 9/1![United Airlines logo]()
$456
This American Airlines deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/217:20 pm -
Nonstop3h 09m
Fri 9/257:00 am -
Nonstop3h 05m
Deal found 9/4![American Airlines logo]()
$469
This Delta deal was found by Cheapflights users on 9/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure 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 11/101:52 pm -
1 stop8h 02m
Deal found 9/2![Delta logo]()
$476
This American Airlines deal was found by Cheapflights users on 9/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/76:59 am -
1 stop6h 25m
Tue 11/107:30 am -
1 stop7h 30m
Deal found 9/2![American Airlines logo]()
$476
This United Airlines deal was found by Cheapflights users on 9/1. 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 12/217:20 am -
Nonstop3h 34m
Thu 12/248:15 am -
Nonstop3h 08m
Deal found 9/1![United Airlines logo]()
$483
This United Airlines deal was found by Cheapflights users on 9/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/51:30 pm -
1 stop4h 27m
Fri 11/66:09 pm -
1 stop4h 50m
Deal found 9/2![United Airlines logo]()
$484
This United Airlines deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/31:30 pm -
1 stop4h 27m
Sat 11/711:54 am -
Nonstop3h 06m
Deal found 9/5![United Airlines logo]()
$486
This United Airlines deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/77:45 pm -
Nonstop3h 08m
Thu 9/108:21 am -
Nonstop3h 08m
Deal found 9/5![United Airlines logo]()
$489
This Delta deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/36:04 am -
1 stop6h 20m
Sat 11/77:30 am -
2 stops9h 30m
Deal found 9/5![Delta logo]()
$501
This Delta deal was found by Cheapflights users on 9/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure 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 11/91:52 pm -
1 stop8h 02m
Deal found 9/2![Delta logo]()
$539
This Delta deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/46:04 am -
1 stop6h 20m
Sat 11/77:30 am -
1 stop6h 47m
Deal found 9/4![Delta logo]()
$559
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 September 6, 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 September 6, 2026.
This United Airlines deal was found by Cheapflights users on 9/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/193:56 pm -
1 stop5h 37m
Fri 12/412:45 pm -
Nonstop3h 00m
Deal found 9/2![United Airlines logo]()
$466
This Delta deal was found by Cheapflights users on 9/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/196:00 am -
1 stop6h 43m
Fri 12/41:56 pm -
1 stop7h 59m
Deal found 9/2![Delta logo]()
$476
This United Airlines deal was found by Cheapflights users on 9/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/147:47 pm -
Nonstop3h 08m
Thu 9/1712:20 pm -
Nonstop3h 04m
Deal found 9/2![United Airlines logo]()
$469
This Delta deal was found by Cheapflights users on 9/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure 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 11/101:52 pm -
1 stop8h 02m
Deal found 9/2![Delta logo]()
$476
This United Airlines deal was found by Cheapflights users on 9/1. 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 9/283:50 pm -
1 stop5h 41m
Wed 9/3012:15 pm -
Nonstop3h 04m
Deal found 9/1![United Airlines logo]()
$479
This Delta deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/36:04 am -
1 stop6h 20m
Sat 11/77:30 am -
1 stop6h 47m
Deal found 9/5![Delta logo]()
$496
This United Airlines deal was found by Cheapflights users on 9/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/51:30 pm -
1 stop4h 27m
Fri 11/66:09 pm -
1 stop4h 50m
Deal found 9/2![United Airlines logo]()
$484
This United Airlines deal was found by Cheapflights users on 9/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/125:00 am -
1 stop6h 36m
Fri 10/161:15 pm -
1 stop7h 37m
Deal found 9/2![United Airlines logo]()
$503
This Delta deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/46:04 am -
1 stop6h 20m
Sat 11/77:30 am -
2 stops9h 30m
Deal found 9/4![Delta logo]()
$564
This United Airlines deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/47:00 am -
1 stop4h 46m
Sat 11/711:54 am -
Nonstop3h 06m
Deal found 9/4![United Airlines logo]()
$529
This United Airlines deal was found by Cheapflights users on 9/3. 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 12/37:15 am -
1 stop4h 16m
Sun 12/69:00 am -
Nonstop3h 09m
Deal found 9/3![United Airlines logo]()
$529
This United Airlines deal was found by Cheapflights users on 9/3. 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 10/166:00 am -
1 stop7h 34m
Sun 10/186:05 pm -
1 stop4h 54m
Deal found 9/3![United Airlines logo]()
$629
This United Airlines deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/39:10 am -
Nonstop3h 19m
Mon 12/149:00 am -
Nonstop3h 09m
Deal found 9/4![United Airlines logo]()
$664
This Delta deal was found by Cheapflights users on 9/1. 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 10/46:05 am -
1 stop6h 16m
Tue 10/137:30 am -
1 stop7h 44m
Deal found 9/1![Delta logo]()
$1,006
This United Airlines deal was found by Cheapflights users on 9/1. 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 9/169:00 am -
Nonstop3h 10m
Sun 9/206:05 pm -
1 stop4h 54m
Deal found 9/1![United Airlines logo]()
$682
This Delta deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/176:04 am -
1 stop6h 20m
Mon 10/197:30 am -
1 stop7h 44m
Deal found 9/5![Delta logo]()
$1,214
This Delta deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/116:05 am -
1 stop6h 16m
Mon 9/147:35 am -
1 stop7h 40m
Deal found 9/5![Delta logo]()
$1,327
This Delta deal was found by Cheapflights users on 9/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure 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
Fri 11/67:30 am -
2 stops9h 30m
Deal found 9/2![Delta logo]()
$1,678
Last-minute flights from Chicago to AspenDiscover last-minute flight deals from Chicago to Aspen. Data last updated September 6, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Aspen. Data last updated September 6, 2026 and is based on user searches.
This United Airlines deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/77:45 pm -
Nonstop3h 08m
Thu 9/108:21 am -
Nonstop3h 08m
Deal found 9/5![United Airlines logo]()
$489
This Delta deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/76:05 am -
1 stop6h 18m
Thu 9/107:35 am -
1 stop6h 49m
Deal found 9/5![Delta logo]()
$763
This American Airlines deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/217:20 pm -
Nonstop3h 09m
Fri 9/257:00 am -
Nonstop3h 05m
Deal found 9/4![American Airlines logo]()
$469
This Delta deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/216:05 am -
1 stop6h 16m
Fri 9/257:35 am -
1 stop7h 40m
Deal found 9/4![Delta logo]()
$869
This American Airlines deal was found by Cheapflights users on 9/1. 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 10/47:20 pm -
Nonstop3h 09m
Tue 10/1312:48 pm -
Nonstop3h 17m
Deal found 9/1![American Airlines logo]()
$393
This United Airlines deal was found by Cheapflights users on 9/1. 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 10/47:00 am -
1 stop4h 36m
Tue 10/138:21 am -
Nonstop3h 08m
Deal found 9/1![United Airlines logo]()
$403
This Delta deal was found by Cheapflights users on 9/1. 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 10/46:05 am -
1 stop6h 16m
Tue 10/137:30 am -
1 stop7h 44m
Deal found 9/1![Delta logo]()
$651
This Delta deal was found by Cheapflights users on 9/6. 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 10/66:04 am -
1 stop6h 17m
Tue 10/137:30 am -
1 stop7h 44m
Deal found 9/6![Delta logo]()
$566
This United Airlines deal was found by Cheapflights users on 9/1. 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 10/109:10 am -
Nonstop3h 19m
Wed 10/1412:15 pm -
Nonstop3h 04m
Deal found 9/1![United Airlines logo]()
$456
This Delta deal was found by Cheapflights users on 9/1. 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 10/106:04 am -
1 stop6h 20m
Wed 10/147:30 am -
1 stop7h 44m
Deal found 9/1![Delta logo]()
$476
This United Airlines deal was found by Cheapflights users on 9/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/127:50 pm -
Nonstop3h 08m
Fri 10/168:21 am -
Nonstop3h 08m
Deal found 9/2![United Airlines logo]()
$483
This Delta deal was found by Cheapflights users on 9/3. 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 10/226:04 am -
1 stop6h 17m
Sun 10/257:30 am -
1 stop7h 44m
Deal found 9/3![Delta logo]()
$1,029
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 September 6, 2026.
Search for one-way flight options from Chicago to Aspen. Find affordable one-way fares based on user searches. Data last updated September 6, 2026.
This American Airlines deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/47:20 pm -
Nonstop3h 09m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/4![American Airlines logo]()
$197
This Delta deal was found by Cheapflights users on 9/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/45:30 am -
1 stop6h 51m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/2![Delta logo]()
$207
This Delta deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/86:04 am -
1 stop6h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/5![Delta logo]()
$217
This Delta deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/65:27 am -
1 stop6h 54m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/4![Delta logo]()
$217
This United Airlines deal was found by Cheapflights users on 9/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/147:47 pm -
Nonstop3h 08m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/2![United Airlines logo]()
$235
This Delta deal was found by Cheapflights users on 9/3. 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 12/15:30 am -
1 stop7h 11m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/3![Delta logo]()
$240
This American Airlines deal was found by Cheapflights users on 9/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/27:05 am -
Nonstop3h 28m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/2![American Airlines logo]()
$242
This American Airlines deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/29:24 am -
2 stops11h 53m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/3![American Airlines logo]()
$243
This Delta deal was found by Cheapflights users on 9/3. 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 9/216:05 am -
1 stop6h 16m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/3![Delta logo]()
$245
This Delta deal was found by Cheapflights users on 9/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/295:30 am -
1 stop6h 51m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/2![Delta logo]()
$245
This United Airlines deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/74:10 pm -
Nonstop3h 06m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/4![United Airlines logo]()
$252
This American Airlines deal was found by Cheapflights users on 9/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/27:20 pm -
Nonstop3h 09m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/2![American Airlines logo]()
$268
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 September 6, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $393 (American Airlines) |
One-way from | $197 (American Airlines) |
Popular in | June |
Cheapest in | August |
Average price | $539 |
Good round-trip deal | $479 or less |
Good one-way deal | $247 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 September 6, 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 3/1
1:00 pm-3:19 pm
Nonstop3h 19m
Aspen Pitkin County
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$197
ChicagoAspen
MDW Chicago Midway - ASE Aspen Pitkin County
MDWASE
Chicago Midway
Sun 11/8
6:04 am-11:24 am
1 stop6h 20m
Aspen Pitkin County
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$217
ChicagoAspen
ORD Chicago O'Hare Intl - ASE Aspen Pitkin County
ORDASE
Chicago O'Hare Intl
Tue 10/6
5:27 am-11:21 am
1 stop6h 54m
Aspen Pitkin County
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$217
ChicagoAspen
ORD Chicago O'Hare Intl - ASE Aspen Pitkin County
ORDASE
Chicago O'Hare Intl
Tue 10/6
9:10 am-11:29 am
Nonstop3h 19m
Aspen Pitkin County
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$242
ChicagoAspen
MDW Chicago Midway - ASE Aspen Pitkin County
MDWASE
Chicago Midway
Mon 9/21
6:05 am-11:21 am
1 stop6h 16m
Aspen Pitkin County
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$245
Quickest round-trip
ChicagoAspen
ORD Chicago O'Hare Intl - ASE Aspen Pitkin County
ORDASE
Chicago O'Hare Intl
Wed 3/3
7:35 am-9:41 am
Nonstop3h 06m
Aspen Pitkin County
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$268
ChicagoAspen
MDW Chicago Midway - ASE Aspen Pitkin County
MDWASE
Chicago Midway
Sat 10/10
6:04 am-11:24 am
1 stop6h 20m
Aspen Pitkin County
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$278
ChicagoAspen
ORD Chicago O'Hare Intl - ASE Aspen Pitkin County
ORDASE
Chicago O'Hare Intl
Fri 3/5
3:35 pm-5:41 pm
Nonstop3h 06m
Aspen Pitkin County
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$278
ChicagoAspen
ORD Chicago O'Hare Intl - ASE Aspen Pitkin County
ORDASE
Chicago O'Hare Intl
Fri 10/2
2:30 pm-8:21 pm
1 stop6h 51m
Aspen Pitkin County
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$278
ChicagoAspen
ORD Chicago O'Hare Intl - ASE Aspen Pitkin County
ORDASE
Chicago O'Hare Intl
Fri 10/30
5:27 am-11:21 am
1 stop6h 54m
Aspen Pitkin County
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$278
Showing 1-10 of 36 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 September.
| 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 December is currently the most expensive (average of $681). 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 September 6, 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 at noon could potentially save you up to 37% on airfare.
How much does it cost to fly round-trip from Chicago to Aspen?
Airfare is below average for this route at the moment.
Chicago to Aspen flights typically cost between $509 and $645 in October.The cheapest round-trip price found within the last 5 days was $393 on American Airlines (Oct 4-Oct 13).
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.
What is the cheapest day to fly from Chicago to Aspen?
Use this chart to determine the cheapest time to fly round-trip from Chicago to Aspen. Price data was last updated on August 29, 2026.
Travelers seeking maximum savings on their Chicago to Aspen flight should consider departing on Friday evenings when fares are most often at their lowest. Saturday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
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 September 6, 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.
Food
6.6
Boarding
7.7
Entertainment
7.1
Crew
8.1
Overall
7.4
Comfort
7.3
Reviews
1 / 20
2.0
MediocreDawn,Aug 2026
ORD - DEN
Food
6.6
Boarding
7.7
Entertainment
7.1
Crew
8.1
Overall
7.4
Comfort
7.3
Reviews
1 / 20
2.0
MediocreDawn,Aug 2026
ORD - DEN
Food
6.6
Boarding
7.7
Entertainment
7.1
Crew
8.1
Overall
7.4
Comfort
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
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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 September 6, 2026.
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Chicago and Aspen flights
Browse other Chicago and Aspen flight options. Last updated on September 6, 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 September 6, 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 September 6, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$259 | Average$502 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$304 | Average$466 | FlexibilityNo cancel fee | On-time71% |