Chicago→Aspen
Chicago Executive Airport (KPWK) — Aspen/Pitkin County Airport (KASE)
10 Empty Legs Available Now
Chicago to Aspen is a key Midwest ski corridor with strong seasonal demand. Affluent Chicago-area travelers drive weekend charter traffic to Aspen, generating return empty legs at discounts of 50-65%.
The route requires super-midsize or larger aircraft capable of handling Aspen's high-altitude approach. The Challenger 350 and Citation Latitude are popular choices, offering both the performance needed and comfortable cabins for the 2.5-hour flight.
Midwest ski travelers heading to Aspen for weekends create repositioning flights back to Chicago.
Sunday and Monday during ski season (Dec-Mar), with peaks around holiday weeks.
Weekly opportunities during ski season, with multiple legs available on peak holiday weekends.