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Chicago metropolitan area

Empty Leg Flights Chicago

Chicago is a major private aviation market linking the Midwest with New York, Florida, Texas, Colorado, and the West Coast. Chicago Executive and Midway are frequent choices for business aviation close to the city.

Current Chicago empty legs

8 current routes across the city’s main private aviation airports.

Request any route
Embraer Phenom 100 empty leg from Chicago (KORD) to Dayton (KDAY) photo 12 photos

Chicago (KORD)Dayton (KDAY)

Departs today
September 10, 2026 - September 11, 2026
6 passengers
1.0 hours in flight
Embraer Phenom 100 (Entry level jet (VLJ))
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Empty leg price
USD 11,440
Members pay USD 10,400
No payment now — dispatch confirms availability and final price first.
Cessna Citation Sovereign empty leg from Chicago (KMDW) to Grand Rapids (KGRR) photo 12 photos

Chicago (KMDW)Grand Rapids (KGRR)

Departs today
September 10, 2026 - September 11, 2026
9 passengers
1.0 hours in flight
Cessna Citation Sovereign (Super midsize jet)
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Empty leg price
USD 25,840
Members pay USD 23,490
No payment now — dispatch confirms availability and final price first.
Beechcraft Hawker 800XP empty leg from Washington (KIAD) to Chicago (KMDW) photo 12 photos

Washington (KIAD)Chicago (KMDW)

Departs today
September 10, 2026 - September 10, 2026
8 passengers
1.1 hours in flight
Beechcraft Hawker 800XP (Midsize jet)
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Empty leg price
USD 28,960
Members pay USD 26,330
No payment now — dispatch confirms availability and final price first.
Cessna Citation XLS+ empty leg from Chicago (KMDW) to Asheville (KAVL) photo 12 photos

Chicago (KMDW)Asheville (KAVL)

Departs tomorrow
September 11, 2026 - September 11, 2026
8 passengers
1.0 hours in flight
Cessna Citation XLS+ (Midsize jet)
View details →
Empty leg price
USD 26,920
Members pay USD 24,470
No payment now — dispatch confirms availability and final price first.

Planning a Chicago empty leg

Chicago Executive is practical for the northern suburbs, Midway offers direct city access, and DuPage can open different operator inventory to the west. Keeping several airports available improves matching.

How confirmation works

Choose a route or send a custom request. Dispatch verifies the aircraft, operator, schedule, and final whole-aircraft price before you commit. Availability can change before contract; once signed, the empty leg is protected like a full-price charter.

Chicago empty leg FAQ

How do I find empty leg flights in Chicago?

Check the live routes connected to KPWK, KMDW, KORD, KDPA below. Inventory changes with operator schedules, so submit a request as soon as a suitable route appears.

Can I request a custom private jet route from Chicago?

Yes. If no empty leg matches, the charter desk can source a standard one-way, roundtrip, or multi-leg flight from the most practical Chicago airport.

Is the listed price guaranteed?

Dispatch confirms aircraft availability, schedule, and final pricing with the operator before any contract or payment.