Cheap Flights from Chicago to Aspen
Cheap Flights from Chicago to Aspen
Looking for cheap flights from Chicago to Aspen? PointsYeah scans award availability across major airline and bank transfer programs in one place, so travelers can compare the lowest points and cash routes faster. Instead of searching each airline separately, users can see pricing from programs like Chase, Amex, Capital One, Citi, and Bilt side by side.
Award prices from Chicago to Aspen vary by season, cabin, and date, but available award flights can start around 7,500 points one way, with premium cabins available at higher mileage levels. The live search above allows filtering by cabin, airline, stops, or maximum points to find the best award flights from Chicago to Aspen for specific travel dates.
2026-12-17
ORD - ASE
Economy | Non stop | 9+ left
From 7,500 Pts + $25.6
2026-12-18
ORD - ASE
Economy | Non stop | 9+ left
From 7,500 Pts + $25.6
2026-12-19
ORD - ASE
Economy | Non stop | 9+ left
From 7,500 Pts + $25.6
2026-12-20
ORD - ASE
Economy | Non stop | 9+ left
From 7,500 Pts + $25.6
2026-12-21
ORD - ASE
Economy | Non stop | 9+ left
From 7,500 Pts + $25.6
2026-12-22
ORD - ASE
Economy | Non stop | 9+ left
From 7,500 Pts + $25.6
Chicago to Aspen flight facts
Distance
1,007 mi
1,621 km in a straight line
Estimated flight time
about 2h 30m
In the air, for the straight-line distance
Time difference
−1h
Aspen is 1 hour behind Chicago.
Airports in Chicago
DPA · Dupage
MDW · Chicago Midway Intl
ORD · Chicago O'Hare Intl
Airports in Aspen
ASE · Aspen-Pitkin Co/Sardy Field
Nearby airport alternatives
Flights Chicago - Vail · Vail is 29 mi from Aspen
Flights Chicago - Gunnison · Gunnison is 48 mi from Aspen
Flights Chicago - Montrose CO · Montrose CO is 74 mi from Aspen
Flights South Bend - Aspen · South Bend is 86 mi from Chicago
Flights Chicago - Hayden · Hayden is 89 mi from Aspen
Flights Chicago - Colorado Springs · Colorado Springs is 120 mi from Aspen
Premium cabin flights from Chicago to Aspen
Premium cabin
2026-11-05
ORD - ASE
First | 1 Stop | 4 left
From 35,000 Pts + $25.6
Premium cabin
2026-11-07
ORD - ASE
First | 1 Stop | 1 left
From 35,000 Pts + $25.6
Premium cabin
2026-11-08
ORD - ASE
First | 1 Stop | 2 left
From 35,000 Pts + $25.6
Premium cabin
2026-11-10
ORD - ASE
First | 1 Stop | 2 left
From 35,000 Pts + $25.6
Premium cabin
2026-11-11
ORD - ASE
First | 1 Stop | 4 left
From 35,000 Pts + $25.6
Premium cabin
2026-11-12
ORD - ASE
First | 1 Stop | 4 left
From 35,000 Pts + $25.6
Selected hotels for your next stay
No hotels available at the moment. Check back soon!
Frequently Asked Questions
The cheapest route from Chicago to Aspen depends on award space, transfer bonuses, and travel dates. PointsYeah compares bank and airline programs in one place so you can find the best points and cash combinations faster.
Yes. Transferable points from Chase, Amex, Capital One, Citi, and Bilt can often be moved to airline partners for flights from Chicago to Aspen.
Yes. Searching metro codes when available helps compare nearby airport combinations for flights from Chicago to Aspen.
Chicago and Aspen are about 1,007 miles (1,621 km) apart in a straight line.
Flying the 1,007-mile straight-line distance takes about 2h 30m in the air, estimated from typical cruising speed. Actual travel time depends on the routing; itineraries with connections take longer.
Aspen is 1 hour behind Chicago.
Departures from Chicago: Dupage (DPA), Chicago Midway Intl (MDW), Chicago O'Hare Intl (ORD). Arrivals in Aspen: Aspen-Pitkin Co/Sardy Field (ASE).
Travelers searching this route also look at other popular routes into Aspen, plus the return trip when we track it. Fares and award space change daily.
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