$207+ 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 10/29. Fares are subject to change and may not be available on all flights or dates of travel.
ASE — CHI
Oct 30 — Nov 61
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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Last-minute
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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 September 30, 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 September 30, 2026.
This United Airlines deal was found by Cheapflights users on 9/27. 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 11/133:18 pm -
1 stop6h 28m
Sun 11/157:00 am -
1 stop4h 42m
Deal found 9/27![United Airlines logo]()
$433
This United Airlines deal was found by Cheapflights users on 9/28. 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 11/286:09 pm -
1 stop4h 50m
Tue 12/14:15 pm -
Nonstop3h 22m
Deal found 9/28![United Airlines logo]()
$466
This United Airlines deal was found by Cheapflights users on 9/27. 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
Fri 12/44:15 pm -
Nonstop3h 22m
Deal found 9/27![United Airlines logo]()
$484
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 10/712:48 pm -
Nonstop3h 17m
Sun 10/1110:00 am -
Nonstop3h 16m
Deal found 9/30![American Airlines logo]()
$489
This United Airlines deal was found by Cheapflights users on 9/29. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/31:30 pm -
1 stop7h 00m
Thu 11/51:30 pm -
1 stop4h 27m
Deal found 9/29![United Airlines logo]()
$504
This United Airlines deal was found by Cheapflights users on 9/27. 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 10/22:15 pm -
1 stop5h 07m
Sun 10/47:00 am -
1 stop4h 36m
Deal found 9/27![United Airlines logo]()
$509
This Delta deal was found by Cheapflights users on 9/29. 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 10/167:30 am -
2 stops12h 00m
Sun 10/185:27 am -
1 stop6h 54m
Deal found 9/29![Delta logo]()
$514
This American Airlines deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/912:48 pm -
Nonstop3h 17m
Mon 10/125:00 am -
1 stop8h 26m
Deal found 9/28![American Airlines logo]()
$523
This United Airlines deal was found by Cheapflights users on 9/28. 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 10/138:21 am -
Nonstop3h 08m
Sat 10/177:50 pm -
Nonstop3h 08m
Deal found 9/28![United Airlines logo]()
$524
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 September 30, 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 September 30, 2026.
This United Airlines deal was found by Cheapflights users on 9/29. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/168:21 am -
Nonstop3h 08m
Mon 10/199:10 am -
Nonstop3h 19m
Deal found 9/29![United Airlines logo]()
$489
This Delta deal was found by Cheapflights users on 9/29. 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.
Tue 11/37:30 am -
2 stops12h 00m
Thu 11/55:27 am -
1 stop6h 57m
Deal found 9/29![Delta logo]()
$509
This United Airlines deal was found by Cheapflights users on 9/29. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/168:21 am -
Nonstop3h 08m
Sun 10/187:50 pm -
Nonstop3h 08m
Deal found 9/29![United Airlines logo]()
$489
This Delta deal was found by Cheapflights users on 9/27. 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 10/237:30 am -
2 stops12h 57m
Mon 10/265:27 am -
1 stop6h 54m
Deal found 9/27![Delta logo]()
$514
This United Airlines deal was found by Cheapflights users on 9/27. 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
Fri 12/412:29 pm -
1 stop5h 03m
Deal found 9/27![United Airlines logo]()
$494
This Delta deal was found by Cheapflights users on 9/29. 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 10/167:30 am -
2 stops11h 08m
Mon 10/195:27 am -
1 stop6h 54m
Deal found 9/29![Delta logo]()
$549
This United Airlines deal was found by Cheapflights users on 9/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/306:09 pm -
1 stop4h 50m
Fri 12/44:15 pm -
Nonstop3h 22m
Deal found 9/27![United Airlines logo]()
$565
This United Airlines deal was found by Cheapflights users on 9/25. 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 -
Nonstop3h 08m
Mon 10/267:00 am -
1 stop6h 48m
Deal found 9/25![United Airlines logo]()
$571
Last-minute flights from Aspen to ChicagoDiscover last-minute flight deals from Aspen to Chicago. Data last updated September 30, 2026 and is based on user searches.
Discover last-minute flight deals from Aspen to Chicago. Data last updated September 30, 2026 and is based on user searches.
This United Airlines deal was found by Cheapflights users on 9/27. 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 10/22:15 pm -
1 stop5h 07m
Sun 10/47:00 am -
1 stop4h 36m
Deal found 9/27![United Airlines logo]()
$509
This Delta deal was found by Cheapflights users on 9/29. 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 10/27:35 am -
2 stops12h 58m
Sun 10/45:30 am -
1 stop6h 51m
Deal found 9/29![Delta logo]()
$568
This American Airlines deal was found by Cheapflights users on 9/27. 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 10/37:00 am -
Nonstop3h 05m
Mon 10/510:00 am -
Nonstop3h 16m
Deal found 9/27![American Airlines logo]()
$567
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 10/712:48 pm -
Nonstop3h 17m
Sun 10/1110:00 am -
Nonstop3h 16m
Deal found 9/30![American Airlines logo]()
$489
This American Airlines deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/912:48 pm -
Nonstop3h 17m
Mon 10/125:00 am -
1 stop8h 26m
Deal found 9/28![American Airlines logo]()
$523
This United Airlines deal was found by Cheapflights users on 9/28. 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 10/138:21 am -
Nonstop3h 08m
Sat 10/177:50 pm -
Nonstop3h 08m
Deal found 9/28![United Airlines logo]()
$524
This American Airlines deal was found by Cheapflights users on 9/28. 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 10/1312:56 pm -
1 stop8h 14m
Sat 10/1710:00 am -
Nonstop3h 16m
Deal found 9/28![American Airlines logo]()
$534
This Delta deal was found by Cheapflights users on 9/29. 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 10/167:30 am -
2 stops12h 00m
Sun 10/185:27 am -
1 stop6h 54m
Deal found 9/29![Delta logo]()
$514
This Delta deal was found by Cheapflights users on 9/29. 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 10/167:30 am -
2 stops11h 08m
Mon 10/195:27 am -
1 stop6h 54m
Deal found 9/29![Delta logo]()
$549
This United Airlines deal was found by Cheapflights users on 9/25. 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 -
Nonstop3h 08m
Mon 10/267:00 am -
1 stop6h 48m
Deal found 9/25![United Airlines logo]()
$571
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 September 30, 2026.
Search for one-way flight options from Aspen to Chicago. Find affordable one-way fares based on user searches. Data last updated September 30, 2026.
This American Airlines deal was found by Cheapflights users on 9/29. 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.
Thu 10/2912:48 pm -
Nonstop3h 17m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/29![American Airlines logo]()
$207
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.
Thu 11/262:22 pm -
1 stop7h 58m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/30![Delta logo]()
$217
This Delta deal was found by Cheapflights users on 9/25. 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 10/277:30 am -
2 stops12h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/25![Delta logo]()
$222
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.
Tue 10/1312:15 pm -
Nonstop3h 04m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/30![United Airlines logo]()
$245
This Delta deal was found by Cheapflights users on 9/25. 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 10/237:30 am -
2 stops12h 57m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/25![Delta logo]()
$260
This American Airlines deal was found by Cheapflights users on 9/27. 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 10/2712:48 pm -
Nonstop3h 17m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/27![American Airlines logo]()
$262
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.
Fri 11/273:18 pm -
1 stop6h 28m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/30![United Airlines logo]()
$272
This American Airlines deal was found by Cheapflights users on 9/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/2612:48 pm -
Nonstop3h 17m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/27![American Airlines logo]()
$278
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 12/131:00 pm -
1 stop7h 11m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/30![American Airlines logo]()
$288
This Delta deal was found by Cheapflights users on 9/29. 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.
Sat 10/317:30 am -
2 stops12h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/29![Delta logo]()
$293
This United Airlines deal was found by Cheapflights users on 9/25. 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 10/238:21 am -
Nonstop3h 08m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/25![United Airlines logo]()
$300
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 September 30, 2026.
Round-trip from | $433 (United Airlines) |
|---|---|
One-way from | $207 (American Airlines) |
Good round-trip deal | $558 or less |
Good one-way deal | $275 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 September 30, 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
Fri 11/27
3:18 pm-10:46 pm
1 stop6h 28m
Chicago O'Hare Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$217
AspenChicago
ASE Aspen Pitkin County - ORD Chicago O'Hare Intl
ASEORD
Aspen Pitkin County
Wed 12/2
2:30 pm-11:56 pm
1 stop8h 26m
Chicago O'Hare Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$217
AspenChicago
ASE Aspen Pitkin County - ORD Chicago O'Hare Intl
ASEORD
Aspen Pitkin County
Tue 11/24
2:22 pm-11:54 pm
1 stop8h 32m
Chicago O'Hare Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$217
AspenChicago
ASE Aspen Pitkin County - ORD Chicago O'Hare Intl
ASEORD
Aspen Pitkin County
Thu 11/26
2:22 pm-11:20 pm
1 stop7h 58m
Chicago O'Hare Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$217
AspenChicago
ASE Aspen Pitkin County - ORD Chicago O'Hare Intl
ASEORD
Aspen Pitkin County
Tue 10/27
1:30 pm-9:30 pm
1 stop7h 00m
Chicago O'Hare Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$255
AspenChicago
ASE Aspen Pitkin County - ORD Chicago O'Hare Intl
ASEORD
Aspen Pitkin County
Wed 10/21
7:30 am-4:58 pm
1 stop8h 28m
Chicago O'Hare Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$255
Quickest round-trip
AspenChicago
ASE Aspen Pitkin County - ORD Chicago O'Hare Intl
ASEORD
Aspen Pitkin County
Thu 12/24
12:47 pm-4:50 pm
Nonstop3h 03m
Chicago O'Hare Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$262
AspenChicago
ASE Aspen Pitkin County - ORD Chicago O'Hare Intl
ASEORD
Aspen Pitkin County
Fri 10/30
3:18 pm-9:30 pm
1 stop5h 12m
Chicago O'Hare Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$272
AspenChicago
ASE Aspen Pitkin County - ORD Chicago O'Hare Intl
ASEORD
Aspen Pitkin County
Sat 10/31
7:30 am-5:47 pm
1 stop9h 17m
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
Sun 11/22
2:22 pm-11:54 pm
1 stop8h 32m
Chicago O'Hare Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$288
Showing 1-10 of 18 resultsSorted by cheapest first
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 September 30, 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 September 30, 2026.
The most flights from ASE to CHI are scheduled on a Monday (5 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (4 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 September 30, 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
Food
6.7
Boarding
7.7
Comfort
7.3
Crew
8.1
Overall
7.4
Reviews
1 / 20
4.0
OkayChris,Aug 2026
MIA - ORD
Entertainment
7.1
Food
6.7
Boarding
7.7
Comfort
7.3
Crew
8.1
Overall
7.4
Reviews
1 / 20
4.0
OkayChris,Aug 2026
MIA - ORD
Entertainment
7.1
Food
6.7
Boarding
7.7
Comfort
7.3
Crew
8.1
Overall
7.4
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
Lansing
Merrillville
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 September 30, 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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Find flights from Aspen to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Aspen and Chicago flights
Browse other Aspen and Chicago flight options. Last updated on September 30, 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 September 30, 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 September 30, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$229 | Average$414 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$376 | Average$533 | FlexibilityNo cancel fee | On-time69% |