Private jet from Chicago — cost to the top 10 summer destinations
DEPARTURE · CHICAGO EXECUTIVE (PWK), MIDWAY (MDW)CURRENCY · USD
Each destination below has its own indexable cost page with a dedicated canonical URL, aircraft-by-aircraft pricing for 2026, FBO recommendations and seasonality notes.
#1 · USA
Chicago → Aspen
ASE · 2h 30m
From $15,000 one-way (light jet)
VIEW COST →#2 · USA
Chicago → Jackson Hole
JAC · 2h 50m
From $17,000 one-way (light jet)
VIEW COST →#3 · USA
Chicago → Bozeman
BZN · 2h 50m
From $17,000 one-way (light jet)
VIEW COST →#4 · USA
Chicago → Nantucket
ACK · 2h 30m
From $16,500 one-way (light jet)
VIEW COST →#5 · USA
Chicago → East Hampton
HTO · 2h 20m
From $15,500 one-way (light jet)
VIEW COST →#6 · USA
Chicago → Miami
OPF · 2h 30m
From $15,000 one-way (light jet)
VIEW COST →#7 · MEXICO
Chicago → Cabo San Lucas
SJD · 4h 30m
From $27,000 one-way (light jet)
VIEW COST →#8 · MEXICO
Chicago → Cancún
CUN · 3h 20m
From $20,000 one-way (light jet)
VIEW COST →#9 · BAHAMAS
Chicago → Bahamas (Nassau)
NAS · 2h 50m
From $17,000 one-way (light jet)
VIEW COST →#10 · CANADA
Chicago → Vancouver
YVR · 4h 00m
From $24,000 one-way (light jet)
VIEW COST →
OTHER ORIGIN CITIES