$207+ 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 3/1. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — ASE
Nov 4 — Nov 111
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 Friday
Cheap flight deals from Chicago to Aspen
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Best
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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 5, 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 5, 2026.
This American Airlines deal was found by Cheapflights users on 10/4. 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.
Tue 12/2212:30 pm -
Nonstop3h 44m
Fri 12/251:14 pm -
Nonstop3h 15m
Deal found 10/4![American Airlines logo]()
$414
This Delta deal was found by Cheapflights users on 9/30. 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 10/146:04 am -
1 stop6h 17m
Wed 10/217:30 am -
1 stop7h 44m
Deal found 9/30![Delta logo]()
$453
This Delta deal was found by Cheapflights users on 9/30. 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 10/145:27 am -
1 stop6h 54m
Wed 10/217:30 am -
1 stop8h 28m
Deal found 9/30![Delta logo]()
$453
This American Airlines deal was found by Cheapflights users on 9/30. 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 10/2210:00 am -
Nonstop3h 16m
Fri 10/3012:48 pm -
Nonstop3h 17m
Deal found 9/30![American Airlines logo]()
$455
This United Airlines deal was found by Cheapflights users on 10/2. 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.
Tue 12/14:15 pm -
Nonstop3h 22m
Sun 12/69:00 am -
Nonstop3h 09m
Deal found 10/2![United Airlines logo]()
$456
This American Airlines deal was found by Cheapflights users on 9/30. 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 10/255:00 am -
1 stop8h 26m
Fri 10/3012:48 pm -
Nonstop3h 17m
Deal found 9/30![American Airlines logo]()
$461
This Delta deal was found by Cheapflights users on 9/30. 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 9/30![Delta logo]()
$476
This Delta deal was found by Cheapflights users on 10/2. 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
Sun 11/87:30 am -
1 stop7h 31m
Deal found 10/2![Delta logo]()
$519
This Delta deal was found by Cheapflights users on 10/1. 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.
Fri 10/236:04 am -
1 stop6h 17m
Mon 10/267:30 am -
2 stops9h 30m
Deal found 10/1![Delta logo]()
$524
This Delta deal was found by Cheapflights users on 10/3. 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.
Fri 11/66:04 am -
1 stop6h 20m
Thu 11/192:22 pm -
1 stop7h 32m
Deal found 10/3![Delta logo]()
$692
This Delta deal was found by Cheapflights users on 10/4. 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 12/226:00 am -
1 stop9h 11m
Fri 12/252:51 pm -
1 stop6h 31m
Deal found 10/4![Delta logo]()
$811
This Delta deal was found by Cheapflights users on 9/30. 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
Thu 10/227:30 am -
1 stop7h 44m
Deal found 9/30![Delta logo]()
$909
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 5, 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 5, 2026.
This United Airlines deal was found by Cheapflights users on 9/30. 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 1/39:10 am -
Nonstop3h 38m
Fri 1/83:31 pm -
1 stop5h 00m
Deal found 9/30![United Airlines logo]()
$423
This Delta deal was found by Cheapflights users on 10/5. 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 11/76:04 am -
1 stop6h 20m
Tue 11/102:22 pm -
1 stop7h 32m
Deal found 10/5![Delta logo]()
$476
This United Airlines deal was found by Cheapflights users on 10/1. 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.
Fri 1/157:00 am -
1 stop4h 26m
Wed 1/207:30 am -
1 stop4h 51m
Deal found 10/1![United Airlines logo]()
$476
This Delta deal was found by Cheapflights users on 10/2. 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
Sun 11/87:30 am -
1 stop7h 31m
Deal found 10/2![Delta logo]()
$519
This United Airlines deal was found by Cheapflights users on 10/4. 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 12/234:15 pm -
Nonstop3h 31m
Mon 12/2812:47 pm -
Nonstop3h 03m
Deal found 10/4![United Airlines logo]()
$499
This Delta deal was found by Cheapflights users on 10/4. 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 10/206:04 am -
1 stop6h 17m
Mon 10/267:30 am -
1 stop7h 44m
Deal found 10/4![Delta logo]()
$544
This United Airlines deal was found by Cheapflights users on 9/30. 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 12/94:15 pm -
Nonstop3h 22m
Sun 12/137:35 am -
1 stop4h 53m
Deal found 9/30![United Airlines logo]()
$509
This Delta deal was found by Cheapflights users on 10/4. 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.
Fri 10/235:27 am -
1 stop6h 54m
Mon 10/267:30 am -
2 stops12h 00m
Deal found 10/4![Delta logo]()
$554
This United Airlines deal was found by Cheapflights users on 10/4. 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.
Tue 10/205:00 am -
1 stop4h 59m
Mon 10/266:09 pm -
1 stop4h 50m
Deal found 10/4![United Airlines logo]()
$514
This United Airlines deal was found by Cheapflights users on 10/2. 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 stop5h 57m
Sun 11/87:30 am -
1 stop4h 45m
Deal found 10/2![United Airlines logo]()
$519
This United Airlines deal was found by Cheapflights users on 9/30. 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 2/147:35 am -
Nonstop3h 40m
Fri 2/193:30 pm -
1 stop4h 59m
Deal found 9/30![United Airlines logo]()
$533
This United Airlines deal was found by Cheapflights users on 10/3. 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.
Sat 11/78:47 am -
Nonstop3h 26m
Tue 11/1011:23 am -
1 stop7h 42m
Deal found 10/3![United Airlines logo]()
$576
This Delta deal was found by Cheapflights users on 9/30. 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
Thu 10/227:30 am -
1 stop7h 44m
Deal found 9/30![Delta logo]()
$909
This Delta deal was found by Cheapflights users on 10/4. 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 12/236:00 am -
1 stop6h 46m
Mon 12/282:51 pm -
1 stop6h 31m
Deal found 10/4![Delta logo]()
$949
This Delta deal was found by Cheapflights users on 10/2. 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 10/256:04 am -
1 stop6h 17m
Fri 10/307:30 am -
1 stop7h 44m
Deal found 10/2![Delta logo]()
$993
This Delta deal was found by Cheapflights users on 10/1. 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.
Fri 1/156:00 am -
1 stop9h 00m
Wed 1/202:55 pm -
1 stop6h 15m
Deal found 10/1![Delta logo]()
$1,261
Last-minute flights from Chicago to AspenDiscover last-minute flight deals from Chicago to Aspen. Data last updated October 5, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Aspen. Data last updated October 5, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 9/30. 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 10/146:04 am -
1 stop6h 17m
Wed 10/217:30 am -
1 stop7h 44m
Deal found 9/30![Delta logo]()
$453
This Delta deal was found by Cheapflights users on 9/30. 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 10/145:27 am -
1 stop6h 54m
Wed 10/217:30 am -
1 stop8h 28m
Deal found 9/30![Delta logo]()
$453
This Delta deal was found by Cheapflights users on 9/30. 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
Thu 10/227:30 am -
1 stop7h 44m
Deal found 9/30![Delta logo]()
$909
This Delta deal was found by Cheapflights users on 10/4. 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 10/206:04 am -
1 stop6h 17m
Mon 10/267:30 am -
1 stop7h 44m
Deal found 10/4![Delta logo]()
$544
This American Airlines deal was found by Cheapflights users on 9/30. 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 10/2210:00 am -
Nonstop3h 16m
Fri 10/3012:48 pm -
Nonstop3h 17m
Deal found 9/30![American Airlines logo]()
$455
This Delta deal was found by Cheapflights users on 10/1. 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.
Fri 10/236:04 am -
1 stop6h 17m
Mon 10/267:30 am -
2 stops9h 30m
Deal found 10/1![Delta logo]()
$524
This American Airlines deal was found by Cheapflights users on 9/30. 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 10/255:00 am -
1 stop8h 26m
Fri 10/3012:48 pm -
Nonstop3h 17m
Deal found 9/30![American Airlines logo]()
$461
This Delta deal was found by Cheapflights users on 10/1. 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 10/256:04 am -
1 stop6h 17m
Fri 10/307:30 am -
1 stop7h 44m
Deal found 10/1![Delta logo]()
$939
This Delta deal was found by Cheapflights users on 10/2. 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
Sun 11/87:30 am -
1 stop7h 31m
Deal found 10/2![Delta logo]()
$519
This Delta deal was found by Cheapflights users on 10/3. 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.
Fri 11/66:04 am -
1 stop6h 20m
Thu 11/192:22 pm -
1 stop7h 32m
Deal found 10/3![Delta logo]()
$692
This Delta deal was found by Cheapflights users on 10/1. 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 11/76:04 am -
1 stop6h 20m
Tue 11/102:22 pm -
1 stop7h 32m
Deal found 10/1![Delta logo]()
$476
This United Airlines deal was found by Cheapflights users on 10/1. 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 11/71:00 pm -
1 stop4h 57m
Tue 11/101:30 pm -
1 stop5h 59m
Deal found 10/1![United Airlines logo]()
$476
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 5, 2026.
Search for one-way flight options from Chicago to Aspen. Find affordable one-way fares based on user searches. Data last updated October 5, 2026.
This United Airlines deal was found by Cheapflights users on 10/4. 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 3/17:35 am -
Nonstop3h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/4![United Airlines logo]()
$207
This Delta deal was found by Cheapflights users on 10/1. 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.
Tue 12/15:30 am -
1 stop7h 11m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/1![Delta logo]()
$217
This United Airlines deal was found by Cheapflights users on 10/1. 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.
Tue 12/159:10 am -
Nonstop3h 26m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/1![United Airlines logo]()
$231
This Delta deal was found by Cheapflights users on 10/2. 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 1/35:25 am -
1 stop7h 21m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/2![Delta logo]()
$237
This American Airlines deal was found by Cheapflights users on 10/1. 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 10/1110:00 am -
Nonstop3h 16m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/1![American Airlines logo]()
$245
This Delta deal was found by Cheapflights users on 10/2. 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.
Mon 3/16:00 am -
1 stop9h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/2![Delta logo]()
$250
This Delta deal was found by Cheapflights users on 10/5. 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 12/65:30 am -
1 stop7h 11m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/5![Delta logo]()
$250
This Delta deal was found by Cheapflights users on 10/1. 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 10/116:04 am -
1 stop6h 17m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/1![Delta logo]()
$255
This Delta deal was found by Cheapflights users on 10/3. 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.
Sun 11/15:27 am -
1 stop6h 57m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/3![Delta logo]()
$255
This United Airlines deal was found by Cheapflights users on 10/5. 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 12/14:15 pm -
Nonstop3h 22m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/5![United Airlines logo]()
$262
This American Airlines deal was found by Cheapflights users on 9/30. 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 3/2812:11 pm -
1 stop9h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/30![American Airlines logo]()
$272
This American Airlines deal was found by Cheapflights users on 9/30. 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 3/37:05 am -
Nonstop3h 28m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/30![American Airlines logo]()
$278
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 5, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $413 (United Airlines) |
One-way from | $207 (United Airlines) |
Popular in | June |
Cheapest in | August |
Average price | $559 |
Good round-trip deal | $499 or less |
Good one-way deal | $277 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 5, 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
Tue 3/30
7:10 am-2:00 pm
1 stop7h 50m
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
Sun 1/3
5:25 am-11:46 am
1 stop7h 21m
Aspen Pitkin County
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$237
ChicagoAspen
MDW Chicago Midway - ASE Aspen Pitkin County
MDWASE
Chicago Midway
Mon 3/1
6:00 am-2:00 pm
1 stop9h 00m
Aspen Pitkin County
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$250
ChicagoAspen
MDW Chicago Midway - ASE Aspen Pitkin County
MDWASE
Chicago Midway
Sun 10/11
6:04 am-11:21 am
1 stop6h 17m
Aspen Pitkin County
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$255
ChicagoAspen
ORD Chicago O'Hare Intl - ASE Aspen Pitkin County
ORDASE
Chicago O'Hare Intl
Sun 11/1
5:27 am-11:24 am
1 stop6h 57m
Aspen Pitkin County
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$255
Quickest round-trip
ChicagoAspen
ORD Chicago O'Hare Intl - ASE Aspen Pitkin County
ORDASE
Chicago O'Hare Intl
Tue 3/30
7:45 pm-9:51 pm
Nonstop3h 06m
Aspen Pitkin County
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$262
ChicagoAspen
ORD Chicago O'Hare Intl - ASE Aspen Pitkin County
ORDASE
Chicago O'Hare Intl
Wed 12/2
9:10 am-11:36 am
Nonstop3h 26m
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 4/2
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
Wed 3/3
5:00 am-11:45 am
1 stop7h 45m
Aspen Pitkin County
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$288
ChicagoAspen
MDW Chicago Midway - ASE Aspen Pitkin County
MDWASE
Chicago Midway
Wed 3/3
6:00 am-2:00 pm
1 stop9h 00m
Aspen Pitkin County
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$288
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 $750). 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 5, 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 30% 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 5, 2026.
The most flights from CHI to ASE are scheduled on a Friday (5 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (3 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.
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 October 3, 2026.
Travelers seeking maximum savings on their Chicago to Aspen flight should consider departing on Sunday 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 October 5, 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
6.7
Overall
7.4
Comfort
7.3
Crew
8.1
Entertainment
7.1
Boarding
7.7
Reviews
1 / 20
2.0
MediocreDawn,Aug 2026
ORD - DEN
Food
6.7
Overall
7.4
Comfort
7.3
Crew
8.1
Entertainment
7.1
Boarding
7.7
Reviews
1 / 20
2.0
MediocreDawn,Aug 2026
ORD - DEN
Food
6.7
Overall
7.4
Comfort
7.3
Crew
8.1
Entertainment
7.1
Boarding
7.7
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 5, 2026.
Complete your trip
Complete your trip to Aspen by adding a car rental and/or hotel reservation to your travel itinerary.
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Chicago and Aspen flights
Browse other Chicago and Aspen flight options. Last updated on October 5, 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 5, 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 5, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$308 | Average$556 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$327 | Average$499 | FlexibilityNo cancel fee | On-time71% |