Departing
Chicago
Madison
Arriving
Madison
✈
Empty Leg Flights from Chicago to Madison
Discounted one-way empty-leg private jet flights from Chicago to Madison. Availability changes daily — set a route alert to catch new legs the moment they list.
Legs available
1
Next available
Aug 18, 2026
Aircraft
Super mid
Price
Est. from $500
1 live Chicago → Madison empty leg
See live aircraft, dates and pricing. No account needed to look — only to request.
View 1 live leg