Cheap Flights from Aspen to Chicago
Cheap Flights from Aspen to Chicago
Looking for cheap flights from Aspen to Chicago? 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 Aspen to Chicago 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 Aspen to Chicago for specific travel dates.
2026-12-17
ASE - ORD
Economy | Non stop | 9+ left
From 7,500 Pts + $25.6
2026-12-18
ASE - ORD
Economy | Non stop | 9+ left
From 7,500 Pts + $25.6
2026-12-19
ASE - ORD
Economy | Non stop | 9+ left
From 7,500 Pts + $25.6
2026-12-20
ASE - ORD
Economy | Non stop | 9+ left
From 7,500 Pts + $25.6
2026-12-21
ASE - ORD
Economy | Non stop | 9+ left
From 7,500 Pts + $25.6
2026-12-22
ASE - ORD
Economy | Non stop | 9+ left
From 7,500 Pts + $25.6
Aspen to Chicago 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
Chicago is 1 hour ahead of Aspen.
Airports in Aspen
ASE · Aspen-Pitkin Co/Sardy Field
Airports in Chicago
DPA · Dupage
MDW · Chicago Midway Intl
ORD · Chicago O'Hare Intl
Nearby airport alternatives
Flights Vail - Chicago · Vail is 29 mi from Aspen
Flights Gunnison - Chicago · Gunnison is 48 mi from Aspen
Flights Montrose CO - Chicago · Montrose CO is 74 mi from Aspen
Flights Aspen - South Bend · South Bend is 86 mi from Chicago
Flights Hayden - Chicago · Hayden is 89 mi from Aspen
Flights Grand Junction - Chicago · Grand Junction is 89 mi from Aspen
Premium cabin flights from Aspen to Chicago
Premium cabin
2026-11-07
ASE - ORD
First | 1 Stop | 5 left
From 35,000 Pts + $25.6
Premium cabin
2026-11-09
ASE - ORD
First | 1 Stop | 1 left
From 35,000 Pts + $25.6
Premium cabin
2026-11-10
ASE - ORD
First | 1 Stop | 3 left
From 35,000 Pts + $25.6
Premium cabin
2026-11-14
ASE - ORD
First | 1 Stop | 2 left
From 35,000 Pts + $25.6
Premium cabin
2026-11-17
ASE - ORD
First | 1 Stop | 4 left
From 35,000 Pts + $25.6
Premium cabin
2026-11-21
ASE - ORD
First | 1 Stop | 1 left
From 35,000 Pts + $25.6
Selected hotels for your next stay
Chicago (United States)
Chicago Athletic Association
From 15,000 Pts or $236
Chicago (USA)
ACME Hotel Chicago, Outset Collection by Hilton
From 28,000 Pts or $75
Chicago, IL (USA)
Waldorf Astoria Chicago
From 95,000 Pts or $407
Frequently Asked Questions
The cheapest route from Aspen to Chicago 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 Aspen to Chicago.
Yes. Searching metro codes when available helps compare nearby airport combinations for flights from Aspen to Chicago.
Aspen and Chicago 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.
Chicago is 1 hour ahead of Aspen.
Departures from Aspen: Aspen-Pitkin Co/Sardy Field (ASE). Arrivals in Chicago: Dupage (DPA), Chicago Midway Intl (MDW), Chicago O'Hare Intl (ORD).
Travelers searching this route also look at other popular routes into Chicago, plus the return trip when we track it. Fares and award space change daily.
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