$231+ Cheap flights from Aspen (ASE) to Chicago (CHI)
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 2/4. Fares are subject to change and may not be available on all flights or dates of travel.
ASE — CHI
Dec 8 — Dec 151
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 November 8, 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 November 8, 2026.
This Delta deal was found by Cheapflights users on 11/7. 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 12/182:30 pm -
1 stop8h 26m
Mon 12/215:25 am -
1 stop7h 21m
Deal found 11/7![Delta logo]()
$463
This United Airlines deal was found by Cheapflights users on 11/4. 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 12/212:45 pm -
Nonstop3h 00m
Wed 12/99:10 am -
Nonstop3h 26m
Deal found 11/4![United Airlines logo]()
$499
This United Airlines deal was found by Cheapflights users on 11/4. 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 11/243:18 pm -
1 stop7h 41m
Tue 12/14:15 pm -
Nonstop3h 22m
Deal found 11/4![United Airlines logo]()
$519
This American Airlines deal was found by Cheapflights users on 11/7. 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 12/101:00 pm -
1 stop8h 15m
Mon 12/143:04 pm -
1 stop6h 20m
Deal found 11/7![American Airlines logo]()
$523
This Delta deal was found by Cheapflights users on 11/3. 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 11/67:30 am -
1 stop8h 28m
Sun 11/85:27 am -
1 stop6h 57m
Deal found 11/3![Delta logo]()
$524
This American Airlines deal was found by Cheapflights users on 11/5. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/137:30 am -
1 stop7h 30m
Mon 11/165:00 am -
1 stop8h 24m
Deal found 11/5![American Airlines logo]()
$539
This American Airlines deal was found by Cheapflights users on 11/7. 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 12/1811:12 am -
Nonstop3h 09m
Mon 12/219:40 am -
Nonstop3h 44m
Deal found 11/7![American Airlines logo]()
$540
This United Airlines deal was found by Cheapflights users on 11/7. 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 12/109:00 am -
Nonstop3h 09m
Mon 12/149:10 am -
Nonstop3h 26m
Deal found 11/7![United Airlines logo]()
$551
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 November 8, 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 November 8, 2026.
This American Airlines deal was found by Cheapflights users on 11/3. 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 1/281:07 pm -
Nonstop3h 15m
Sun 1/319:40 am -
Nonstop3h 57m
Deal found 11/3![American Airlines logo]()
$429
This Delta deal was found by Cheapflights users on 11/7. 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 12/182:30 pm -
1 stop8h 26m
Mon 12/215:25 am -
1 stop7h 21m
Deal found 11/7![Delta logo]()
$463
This United Airlines deal was found by Cheapflights users on 11/4. 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 11/243:18 pm -
1 stop6h 28m
Tue 12/112:59 pm -
1 stop4h 33m
Deal found 11/4![United Airlines logo]()
$529
This American Airlines deal was found by Cheapflights users on 11/7. 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 12/101:00 pm -
1 stop8h 15m
Mon 12/143:04 pm -
1 stop6h 20m
Deal found 11/7![American Airlines logo]()
$523
This United Airlines deal was found by Cheapflights users on 11/7. 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 12/109:00 am -
Nonstop3h 09m
Mon 12/149:10 am -
Nonstop3h 26m
Deal found 11/7![United Airlines logo]()
$551
This Delta deal was found by Cheapflights users on 11/5. 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.
Wed 1/1312:22 pm -
2 stops19h 38m
Tue 1/195:30 am -
1 stop7h 17m
Deal found 11/5![Delta logo]()
$564
This United Airlines deal was found by Cheapflights users on 11/3. 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.
Tue 12/112:45 pm -
Nonstop3h 00m
Tue 12/89:10 am -
Nonstop3h 26m
Deal found 11/3![United Airlines logo]()
$572
This United Airlines deal was found by Cheapflights users on 11/7. 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 12/2912:47 pm -
Nonstop3h 03m
Thu 12/311:10 pm -
Nonstop3h 31m
Deal found 11/7![United Airlines logo]()
$581
Last-minute flights from Aspen to ChicagoDiscover last-minute flight deals from Aspen to Chicago. Data last updated November 8, 2026 and is based on user searches.
Discover last-minute flight deals from Aspen to Chicago. Data last updated November 8, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 11/3. 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 11/67:30 am -
1 stop8h 28m
Sun 11/85:27 am -
1 stop6h 57m
Deal found 11/3![Delta logo]()
$524
This American Airlines deal was found by Cheapflights users on 11/5. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/137:30 am -
1 stop7h 30m
Mon 11/165:00 am -
1 stop8h 24m
Deal found 11/5![American Airlines logo]()
$539
This United Airlines deal was found by Cheapflights users on 11/4. 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 11/243:18 pm -
1 stop7h 41m
Tue 12/14:15 pm -
Nonstop3h 22m
Deal found 11/4![United Airlines logo]()
$519
This United Airlines deal was found by Cheapflights users on 11/4. 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 12/212:45 pm -
Nonstop3h 00m
Wed 12/99:10 am -
Nonstop3h 26m
Deal found 11/4![United Airlines logo]()
$499
This American Airlines deal was found by Cheapflights users on 11/7. 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 12/101:00 pm -
1 stop8h 15m
Mon 12/143:04 pm -
1 stop6h 20m
Deal found 11/7![American Airlines logo]()
$523
This United Airlines deal was found by Cheapflights users on 11/7. 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 12/109:00 am -
Nonstop3h 09m
Mon 12/149:10 am -
Nonstop3h 26m
Deal found 11/7![United Airlines logo]()
$551
This Delta deal was found by Cheapflights users on 11/7. 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 12/182:30 pm -
1 stop8h 26m
Mon 12/215:25 am -
1 stop7h 21m
Deal found 11/7![Delta logo]()
$463
This American Airlines deal was found by Cheapflights users on 11/7. 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 12/1811:12 am -
Nonstop3h 09m
Mon 12/219:40 am -
Nonstop3h 44m
Deal found 11/7![American Airlines logo]()
$540
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 November 8, 2026.
Search for one-way flight options from Aspen to Chicago. Find affordable one-way fares based on user searches. Data last updated November 8, 2026.
This American Airlines deal was found by Cheapflights users on 11/5. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/43:10 pm -
Nonstop3h 17m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/5![American Airlines logo]()
$231
This Delta deal was found by Cheapflights users on 11/5. 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.
Thu 2/43:00 pm -
1 stop7h 57m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/5![Delta logo]()
$232
This American Airlines deal was found by Cheapflights users on 11/3. 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.
Sun 12/2012:05 pm -
Nonstop3h 09m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![American Airlines logo]()
$250
This United Airlines deal was found by Cheapflights users on 11/5. 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 12/112:45 pm -
Nonstop3h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/5![United Airlines logo]()
$260
This Delta deal was found by Cheapflights users on 11/5. 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 11/132:22 pm -
1 stop8h 32m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/5![Delta logo]()
$270
This United Airlines deal was found by Cheapflights users on 11/4. 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 2/14:20 pm -
Nonstop3h 03m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/4![United Airlines logo]()
$288
This United Airlines deal was found by Cheapflights users on 11/7. 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 1/174:20 pm -
Nonstop3h 03m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/7![United Airlines logo]()
$293
This American Airlines deal was found by Cheapflights users on 11/4. 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.
Fri 11/2012:57 pm -
1 stop8h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/4![American Airlines logo]()
$294
This deal was found by Cheapflights users on 11/5. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/136:09 pm -
1 stop4h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/5![United Airlines logo]()
$325
This Delta deal was found by Cheapflights users on 11/5. 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 11/152:22 pm -
1 stop8h 32m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/5![Delta logo]()
$348
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 November 8, 2026.
Most accurate provider | eDreams 2 stars |
|---|---|
Most trusted provider | eDreams 3 stars |
Round-trip from | $429 (American Airlines) |
One-way from | $231 (American Airlines) |
Good round-trip deal | $550 or less |
Good one-way deal | $298 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Aspen to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated November 8, 2026.
Use the filters below to find and compare flights from Aspen to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
AspenChicago
ASE Aspen Pitkin County - ORD Chicago O'Hare Intl
ASEORD
Aspen Pitkin County
Thu 2/4
3:00 pm-11:57 pm
1 stop7h 57m
Chicago O'Hare Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$232
AspenChicago
ASE Aspen Pitkin County - ORD Chicago O'Hare Intl
ASEORD
Aspen Pitkin County
Thu 11/19
3:18 pm-9:30 pm
1 stop5h 12m
Chicago O'Hare Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$270
AspenChicago
ASE Aspen Pitkin County - ORD Chicago O'Hare Intl
ASEORD
Aspen Pitkin County
Fri 11/13
2:22 pm-11:54 pm
1 stop8h 32m
Chicago O'Hare Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$270
AspenChicago
ASE Aspen Pitkin County - ORD Chicago O'Hare Intl
ASEORD
Aspen Pitkin County
Mon 2/1
4:20 pm-8:23 pm
Nonstop3h 03m
Chicago O'Hare Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$288
AspenChicago
ASE Aspen Pitkin County - ORD Chicago O'Hare Intl
ASEORD
Aspen Pitkin County
Mon 2/1
1:07 pm-5:22 pm
Nonstop3h 15m
Chicago O'Hare Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$293
AspenChicago
ASE Aspen Pitkin County - ORD Chicago O'Hare Intl
ASEORD
Aspen Pitkin County
Mon 2/22
6:16 pm-11:59 pm
1 stop4h 43m
Chicago O'Hare Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$293
AspenChicago
ASE Aspen Pitkin County - ORD Chicago O'Hare Intl
ASEORD
Aspen Pitkin County
Sun 11/15
2:22 pm-11:54 pm
1 stop8h 32m
Chicago O'Hare Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$348
Quickest round-trip
AspenChicago
ASE Aspen Pitkin County - ORD Chicago O'Hare Intl
ASEORD
Aspen Pitkin County
Sun 12/13
12:45 pm-4:45 pm
Nonstop3h 00m
Chicago O'Hare Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$348
AspenChicago
ASE Aspen Pitkin County - ORD Chicago O'Hare Intl
ASEORD
Aspen Pitkin County
Thu 2/4
3:00 pm-6:42 am
2 stops14h 42m
Chicago O'Hare Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$363
AspenChicago
ASE Aspen Pitkin County - ORD Chicago O'Hare Intl
ASEORD
Aspen Pitkin County
Mon 2/22
12:15 pm-4:24 pm
Nonstop3h 09m
Chicago O'Hare Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$364
Showing 1-10 of 18 resultsSorted by cheapest first
- Most accurate provider: When it comes to deals on Aspen-Chicago flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Aspen-Chicago flight deals on Cheapflights vs. eDreams 90-95% 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 eDreams the most. eDreams 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
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
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 November 8, 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.
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 November 8, 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.
Comfort
7.3
Entertainment
7.1
Food
6.7
Overall
7.3
Boarding
7.7
Crew
8.1
Reviews
1 / 20
4.0
OkayChris,Aug 2026
MIA - ORD
Comfort
7.3
Entertainment
7.1
Food
6.7
Overall
7.3
Boarding
7.7
Crew
8.1
Reviews
1 / 20
4.0
OkayChris,Aug 2026
MIA - ORD
Comfort
7.3
Entertainment
7.1
Food
6.7
Overall
7.3
Boarding
7.7
Crew
8.1
Reviews
1 / 20
4.0
OkayChris,Aug 2026
MIA - ORD
Related info for your journey
Find useful and relevant information for your journey from Aspen to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsBenton Harbor
Merrillville
Lansing
Valparaiso
Hammond
Saint Joseph
Porter
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
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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 November 8, 2026.
Complete your trip
Complete your trip to Chicago by adding a car rental and/or hotel reservation to your travel itinerary.
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Aspen and Chicago flights
Browse other Aspen and Chicago flight options. Last updated on November 8, 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 November 8, 2026.
Popular flight searches
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 7,457,451 searches. Data last updated November 8, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$229 | Average$414 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$376 | Average$604 | FlexibilityNo cancel fee | On-time69% |