$172+ Cheap flights from Aspen (ASE) to Chicago (CHI)
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 8/19. Fares are subject to change and may not be available on all flights or dates of travel.
ASE — CHI
Aug 4 — Aug 111
Round-trip
1 adult, Economy
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Find cheap flights from Aspen to Chicago with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Aspen to Chicago
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Cheapest flights from Aspen to ChicagoExplore the most affordable flight options available from Aspen to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 5, 2026.
Explore the most affordable flight options available from Aspen to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 5, 2026.
This American Airlines deal was found by Cheapflights users on 7/1. 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.
Wed 8/191:54 pm
ASE
- ORD
Nonstop3h 13m
American Airlines
Sun 8/236:45 pm
ORD
- ASE
Nonstop3h 10m
American Airlines
Deal found 7/1![American Airlines logo]()
$343
This American Airlines deal was found by Cheapflights users on 6/30. 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 7/307:25 am
ASE
- ORD
Nonstop3h 06m
American Airlines
Sun 8/27:49 pm
ORD
- ASE
Nonstop3h 07m
American Airlines
Deal found 6/30![American Airlines logo]()
$344
This American Airlines deal was found by Cheapflights users on 7/3. 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.
Thu 8/67:00 am
ASE
- ORD
Nonstop3h 06m
American Airlines
Sun 8/96:45 pm
ORD
- ASE
Nonstop3h 10m
American Airlines
Deal found 7/3![American Airlines logo]()
$346
This United Airlines deal was found by Cheapflights users on 7/2. 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 10/228:21 am
ASE
- ORD
Nonstop3h 08m
United Airlines
Sun 10/258:45 am
ORD
- ASE
Nonstop3h 19m
United Airlines
Deal found 7/2![United Airlines logo]()
$362
This Delta deal was found by Cheapflights users on 7/2. 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 10/227:30 am
ASE
- MDW
1 stop7h 50m
Delta
Sun 10/256:00 am
MDW
- ASE
1 stop6h 21m
Delta
Deal found 7/2![Delta logo]()
$363
This Delta deal was found by Cheapflights users on 7/2. 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 10/227:30 am
ASE
- ORD
2 stops12h 00m
Delta
Sun 10/255:30 am
ORD
- ASE
1 stop6h 51m
Delta
Deal found 7/2![Delta logo]()
$368
This American Airlines deal was found by Cheapflights users on 6/30. 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.
Sat 9/197:00 am
ASE
- ORD
Nonstop3h 05m
American Airlines
Sun 9/207:20 pm
ORD
- ASE
Nonstop3h 09m
American Airlines
Deal found 6/30![American Airlines logo]()
$406
This Delta deal was found by Cheapflights users on 6/29. 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 7/107:30 am
ASE
- MDW
2 stops9h 48m
Delta
Tue 7/146:00 am
MDW
- ASE
1 stop6h 22m
Delta
Deal found 6/29![Delta logo]()
$1,039
This Delta deal was found by Cheapflights users on 6/29. 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 7/107:30 am
ASE
- MDW
2 stops9h 48m
Delta
Sun 7/126:00 am
MDW
- ASE
1 stop6h 22m
Delta
Deal found 6/29![Delta logo]()
$1,047
This Delta deal was found by Cheapflights users on 7/4. 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.
Sat 9/197:35 am
ASE
- MDW
1 stop6h 50m
Delta
Sun 9/206:05 am
MDW
- ASE
1 stop6h 16m
Delta
Deal found 7/4![Delta logo]()
$1,086
This Delta deal was found by Cheapflights users on 7/3. 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 8/67:20 am
ASE
- MDW
1 stop7h 55m
Delta
Sun 8/96:05 am
MDW
- ASE
1 stop6h 18m
Delta
Deal found 7/3![Delta logo]()
$1,204
This Delta deal was found by Cheapflights users on 6/30. 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.
Fri 7/37:36 am
ASE
- MDW
1 stop7h 04m
Delta
Mon 7/66:00 am
MDW
- ASE
1 stop6h 22m
Delta
Deal found 6/30![Delta logo]()
$1,232
Best flights from Aspen to ChicagoDiscover carefully curated flight deals from Aspen to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated July 5, 2026.
Discover carefully curated flight deals from Aspen to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated July 5, 2026.
This American Airlines deal was found by Cheapflights users on 7/4. 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.
Wed 8/191:54 pm
ASE
- ORD
Nonstop3h 13m
American Airlines
Sun 8/236:45 pm
ORD
- ASE
Nonstop3h 10m
American Airlines
Deal found 7/4![American Airlines logo]()
$343
This United Airlines deal was found by Cheapflights users on 7/2. 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 10/228:21 am
ASE
- ORD
Nonstop3h 08m
United Airlines
Sun 10/258:45 am
ORD
- ASE
Nonstop3h 19m
United Airlines
Deal found 7/2![United Airlines logo]()
$362
This Delta deal was found by Cheapflights users on 7/2. 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 10/227:30 am
ASE
- MDW
1 stop7h 50m
Delta
Sun 10/256:00 am
MDW
- ASE
1 stop6h 21m
Delta
Deal found 7/2![Delta logo]()
$363
This Delta deal was found by Cheapflights users on 7/2. 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 10/227:30 am
ASE
- ORD
1 stop8h 27m
Delta
Sun 10/255:30 am
ORD
- ASE
1 stop6h 51m
Delta
Deal found 7/2![Delta logo]()
$363
This United Airlines deal was found by Cheapflights users on 6/30. 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.
Fri 7/176:12 pm
ASE
- ORD
1 stop5h 32m
United Airlines
Tue 7/218:52 am
ORD
- ASE
Nonstop3h 09m
United Airlines
Deal found 6/30![United Airlines logo]()
$429
This United Airlines deal was found by Cheapflights users on 6/30. 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.
Fri 10/3011:55 am
ASE
- ORD
Nonstop3h 00m
United Airlines
Tue 11/38:45 am
ORD
- ASE
Nonstop3h 19m
United Airlines
Deal found 6/30![United Airlines logo]()
$433
This United Airlines deal was found by Cheapflights users on 6/30. 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.
Sat 9/195:05 pm
ASE
- ORD
2 stops13h 39m
United Airlines
Sun 9/2010:55 am
ORD
- ASE
1 stop5h 13m
United Airlines
Deal found 6/30![United Airlines logo]()
$559
This Delta deal was found by Cheapflights users on 7/4. 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.
Sat 9/197:35 am
ASE
- MDW
1 stop6h 50m
Delta
Sun 9/206:05 am
MDW
- ASE
1 stop6h 16m
Delta
Deal found 7/4![Delta logo]()
$1,086
This Delta deal was found by Cheapflights users on 7/3. 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 8/67:20 am
ASE
- MDW
1 stop7h 55m
Delta
Sun 8/96:05 am
MDW
- ASE
1 stop6h 18m
Delta
Deal found 7/3![Delta logo]()
$1,204
This Delta deal was found by Cheapflights users on 6/29. 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 7/307:30 am
ASE
- MDW
1 stop7h 45m
Delta
Sun 8/26:00 am
MDW
- ASE
1 stop6h 22m
Delta
Deal found 6/29![Delta logo]()
$1,552
This Delta deal was found by Cheapflights users on 6/30. 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 8/197:20 am
ASE
- MDW
1 stop7h 55m
Delta
Sun 8/236:05 am
MDW
- ASE
1 stop6h 18m
Delta
Deal found 6/30![Delta logo]()
$1,605
Last-minute flights from Aspen to ChicagoDiscover last-minute flight deals from Aspen to Chicago. Data last updated July 5, 2026 and is based on user searches.
Discover last-minute flight deals from Aspen to Chicago. Data last updated July 5, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 6/30. 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.
Fri 7/37:25 am
ASE
- ORD
Nonstop3h 06m
American Airlines
Mon 7/67:49 pm
ORD
- ASE
Nonstop3h 07m
American Airlines
Deal found 6/30![American Airlines logo]()
$419
This Delta deal was found by Cheapflights users on 6/30. 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.
Fri 7/37:36 am
ASE
- MDW
1 stop7h 04m
Delta
Mon 7/66:00 am
MDW
- ASE
1 stop6h 22m
Delta
Deal found 6/30![Delta logo]()
$1,232
This American Airlines deal was found by Cheapflights users on 6/29. 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 7/1011:22 am
ASE
- ORD
Nonstop3h 07m
American Airlines
Sun 7/1211:15 am
ORD
- ASE
Nonstop3h 06m
American Airlines
Deal found 6/29![American Airlines logo]()
$420
This Delta deal was found by Cheapflights users on 6/29. 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 7/107:30 am
ASE
- MDW
2 stops9h 48m
Delta
Tue 7/146:00 am
MDW
- ASE
1 stop6h 22m
Delta
Deal found 6/29![Delta logo]()
$1,039
This Delta deal was found by Cheapflights users on 6/29. 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 7/107:30 am
ASE
- MDW
2 stops9h 48m
Delta
Sun 7/126:00 am
MDW
- ASE
1 stop6h 22m
Delta
Deal found 6/29![Delta logo]()
$1,047
This Delta deal was found by Cheapflights users on 7/3. 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.
Wed 7/157:30 am
ASE
- MDW
1 stop7h 45m
Delta
Sun 7/266:00 am
MDW
- ASE
1 stop6h 22m
Delta
Deal found 7/3![Delta logo]()
$1,469
This American Airlines deal was found by Cheapflights users on 6/30. 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 7/307:25 am
ASE
- ORD
Nonstop3h 06m
American Airlines
Sun 8/27:49 pm
ORD
- ASE
Nonstop3h 07m
American Airlines
Deal found 6/30![American Airlines logo]()
$344
This American Airlines deal was found by Cheapflights users on 7/3. 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.
Thu 8/67:00 am
ASE
- ORD
Nonstop3h 06m
American Airlines
Sun 8/96:45 pm
ORD
- ASE
Nonstop3h 10m
American Airlines
Deal found 7/3![American Airlines logo]()
$346
This Delta deal was found by Cheapflights users on 7/3. 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 8/67:20 am
ASE
- MDW
1 stop7h 55m
Delta
Sun 8/96:05 am
MDW
- ASE
1 stop6h 18m
Delta
Deal found 7/3![Delta logo]()
$1,204
This United Airlines deal was found by Cheapflights users on 7/3. 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 8/75:10 pm
ASE
- ORD
1 stop4h 39m
United Airlines
Mon 8/175:00 am
ORD
- ASE
1 stop4h 59m
United Airlines
Deal found 7/3![United Airlines logo]()
$406
This United Airlines deal was found by Cheapflights users on 6/30. 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.
Mon 8/105:10 pm
ASE
- ORD
1 stop5h 09m
United Airlines
Mon 8/177:45 pm
ORD
- ASE
Nonstop3h 08m
United Airlines
Deal found 6/30![United Airlines logo]()
$416
This American Airlines deal was found by Cheapflights users on 7/1. 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.
Wed 8/191:54 pm
ASE
- ORD
Nonstop3h 13m
American Airlines
Sun 8/236:45 pm
ORD
- ASE
Nonstop3h 10m
American Airlines
Deal found 7/1![American Airlines logo]()
$343
One-way flights from Aspen to ChicagoSearch for one-way flight options from Aspen to Chicago. Find affordable one-way fares based on user searches. Data last updated July 5, 2026.
Search for one-way flight options from Aspen to Chicago. Find affordable one-way fares based on user searches. Data last updated July 5, 2026.
This American Airlines deal was found by Cheapflights users on 7/2. 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.
Wed 8/191:54 pm
ASE
- ORD
Nonstop3h 13m
American Airlines
Deal found 7/2![American Airlines logo]()
$172
This United Airlines deal was found by Cheapflights users on 7/2. 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.
Wed 8/192:15 pm
ASE
- ORD
1 stop6h 14m
United Airlines
Deal found 7/2![United Airlines logo]()
$182
This Delta deal was found by Cheapflights users on 7/3. 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 9/37:20 am
ASE
- ORD
2 stops10h 09m
Delta
Deal found 7/3![Delta logo]()
$187
This KAYAK deal was found by Cheapflights users on 7/1. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/147:25 am
ASE
- ORD
Nonstop3h 06m
American Airlines
Deal found 7/1![American Airlines logo]()
$200
This American Airlines deal was found by Cheapflights users on 6/30. 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 7/167:25 am
ASE
- ORD
Nonstop3h 06m
American Airlines
Deal found 6/30![American Airlines logo]()
$210
This United Airlines deal was found by Cheapflights users on 7/1. 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 9/308:21 am
ASE
- ORD
Nonstop3h 08m
United Airlines
Deal found 7/1![United Airlines logo]()
$217
This United Airlines deal was found by Cheapflights users on 7/1. 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.
Thu 7/161:07 pm
ASE
- ORD
1 stop6h 07m
United Airlines
Deal found 7/1![United Airlines logo]()
$220
This United Airlines deal was found by Cheapflights users on 7/1. 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 7/292:22 pm
ASE
- ORD
1 stop5h 18m
United Airlines
Deal found 7/1![United Airlines logo]()
$225
This United Airlines deal was found by Cheapflights users on 7/3. 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 12/3112:20 pm
ASE
- ORD
1 stop6h 23m
United Airlines
Deal found 7/3![United Airlines logo]()
$227
This American Airlines deal was found by Cheapflights users on 7/2. 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.
Sun 8/307:00 am
ASE
- ORD
Nonstop3h 06m
American Airlines
Deal found 7/2![American Airlines logo]()
$243
This United Airlines deal was found by Cheapflights users on 6/30. 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.
Thu 8/2712:10 pm
ASE
- ORD
Nonstop3h 01m
United Airlines
Deal found 6/30![United Airlines logo]()
$244
This Delta deal was found by Cheapflights users on 7/4. 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 7/147:30 am
ASE
- MDW
1 stop7h 45m
Delta
Deal found 7/4![Delta logo]()
$249
Find flight deals from Aspen to Chicago
Discover tips and strategies to find the most affordable flight options for your journey from Aspen (ASE) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated July 5, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $343 (American Airlines) |
One-way from | $172 (American Airlines) |
Good round-trip deal | $488 or less |
Good one-way deal | $265 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Aspen to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated July 5, 2026.
Use the filters below to find and compare flights from Aspen to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
AspenChicago
ASE - ORD
ASEORD
Aspen Pitkin County
Wed 8/19
1:54 pm-6:07 pm
Nonstop3h 13m
Chicago O'Hare Intl
Sun 8/23
6:45 pm-8:55 pm
Nonstop3h 10m
$343
AspenChicago
ASE - ORD
ASEORD
Aspen Pitkin County
Thu 10/22
8:21 am-12:29 pm
Nonstop3h 08m
Chicago O'Hare Intl
Sun 10/25
8:45 am-11:04 am
Nonstop3h 19m
$362
AspenChicago
ASE - MDW
ASEMDW
Aspen Pitkin County
Thu 10/22
7:30 am-4:20 pm
1 stop7h 50m
Chicago Midway
Sun 10/25
6:00 am-11:21 am
1 stop6h 21m
$363
AspenChicago
ASE - ORD
ASEORD
Aspen Pitkin County
Thu 10/22
7:30 am-4:57 pm
1 stop8h 27m
Chicago O'Hare Intl
Sun 10/25
5:30 am-11:21 am
1 stop6h 51m
$363
AspenChicago
ASE - ORD
ASEORD
Aspen Pitkin County
Fri 7/17
6:12 pm-12:44 am
1 stop5h 32m
Chicago O'Hare Intl
Tue 7/21
8:52 am-11:01 am
Nonstop3h 09m
$429
Quickest round-trip
AspenChicago
ASE - ORD
ASEORD
Aspen Pitkin County
Fri 10/30
11:55 am-3:55 pm
Nonstop3h 00m
Chicago O'Hare Intl
Tue 11/3
8:45 am-11:04 am
Nonstop3h 19m
$433
AspenChicago
ASE - ORD
ASEORD
Aspen Pitkin County
Sat 9/19
5:05 pm-7:44 am
2 stops13h 39m
Chicago O'Hare Intl
Sun 9/20
10:55 am-3:08 pm
1 stop5h 13m
$559
AspenChicago
ASE - MDW
ASEMDW
Aspen Pitkin County
Sat 9/19
7:35 am-3:25 pm
1 stop6h 50m
Chicago Midway
Sun 9/20
6:05 am-11:21 am
1 stop6h 16m
$1,086
AspenChicago
ASE - MDW
ASEMDW
Aspen Pitkin County
Thu 8/6
7:20 am-4:15 pm
1 stop7h 55m
Chicago Midway
Sun 8/9
6:05 am-11:23 am
1 stop6h 18m
$1,204
AspenChicago
ASE - MDW
ASEMDW
Aspen Pitkin County
Thu 7/30
7:30 am-4:15 pm
1 stop7h 45m
Chicago Midway
Sun 8/2
6:00 am-11:22 am
1 stop6h 22m
$1,552
Showing 1-10 of 26 resultsSorted by cheapest first
- Most accurate provider: When it comes to deals on Aspen-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Aspen-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Aspen-Chicago flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Aspen-Chicago flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Aspen-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.
Best time to book a flight from Aspen to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Aspen with our price prediction graph.
ASE-CHI
ASE-ORD
ASE-MDW
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Aspen to Chicago
ASE-CHI
ASE-ORD
ASE-MDW
What is the cheapest time of day to fly from ASE to CHI?
Find hourly flight availability from Aspen to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated July 5, 2026.
When flying from Aspen to Chicago, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.
Weekly flight availability from Aspen to Chicago
Explore weekly flight availability from Aspen to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated July 5, 2026.
The most flights from ASE to CHI are scheduled on a Friday (7 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (6 on average).
Reviews of airlines servicing Chicago
Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated July 5, 2026.
Read through reviews of airlines operating flights from Aspen to Chicago, such as United Airlines and American Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Entertainment
7.1
Overall
7.4
Boarding
7.7
Food
6.7
Crew
8.1
Comfort
7.3
Reviews
1 / 20
2.0
MediocreDeb,Jan 2025
MKE - ORD
Entertainment
7.1
Overall
7.4
Boarding
7.7
Food
6.7
Crew
8.1
Comfort
7.3
Reviews
1 / 20
2.0
MediocreDeb,Jan 2025
MKE - ORD
Entertainment
7.1
Overall
7.4
Boarding
7.7
Food
6.7
Crew
8.1
Comfort
7.3
Reviews
1 / 20
2.0
MediocreDeb,Jan 2025
MKE - ORD
Related info for your journey
Find useful and relevant information for your journey from Aspen to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsBenton Harbor
Hammond
Lansing
Merrillville
Valparaiso
Porter
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Other flights to Chicago
Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on July 5, 2026.
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Aspen and Chicago flights
Browse other Aspen and Chicago flight options. Last updated on July 5, 2026.
Other flights from Aspen
Browse through other flights departing from Aspen. Flights are based on user searches made on Cheapflights and were last updated on July 5, 2026.
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Check out other popular destinations found by fellow travelers in 2026
Top 2 airlines flying from Aspen to Chicago
Discover the top 2 airlines that operate flights from Aspen to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated July 5, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$319 | Average$385 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$343 | Average$414 | FlexibilityNo cancel fee | On-time71% |