Empty Leg Flights from & to Chicago

24 private jet empty legs to or from Chicago/Prospect Heights/Wheeling right now, from $18,200 for the whole aircraft. An empty leg is an aircraft flying without passengers, usually to reach its next charter or return to base, so the seats are offered at a fraction of a full charter price.

308 empty legs tracked since September 2026146 departing · 162 arriving9 seats on average

Naples → ChicagoAPF–PWK · Embraer Praetor 600 · 9 seats · ≈ 2h 55mEstimate $16k–29kTomorrow
Naples → ChicagoAPF–PWK · Legacy 500 · 9 seats · ≈ 2h 55mEstimate $14k–26kTomorrow
Omaha → ChicagoOMA–PWK · Bombardier Learjet 45 · 8 seats · ≈ 1h 20mEstimate $4k–8kTomorrow
Chicago → PittsburghPWK–PIT · Cessna Citation Bravo · 7 seats · ≈ 1h 25mEstimate $3k–6k11 Nov
Chicago → AustinPWK–AUS · Hawker 900 XP · 8 seats · ≈ 2h 45mEstimate $12k–21k11 Nov
Chicago → WoodruffPWK–ARV · Citation Excel 560XLS+ · 9 seats · ≈ 1h 05mEstimate $4k–7k11 Nov
Chicago → PittsburghPWK–PIT · Cessna Citation Bravo · 7 seats · ≈ 1h 25mEstimate $3k–6k11 Nov
Chicago → PittsburghPWK–PIT · Cessna Citation Bravo · 7 seats · ≈ 1h 25mEstimate $3k–6k11 Nov
Chicago → TeterboroPWK–TEB · Cessna Citation Bravo · 7 seats · ≈ 2h 15mEstimate $5k–9k13 Nov
Chicago → TeterboroPWK–TEB · Cessna Citation Bravo · 7 seats · ≈ 2h 15mEstimate $5k–9k13 Nov
Chicago → Fort WorthPWK–AFW · IAI Astra SPX · 7 seats · ≈ 2h 10mEstimate $8k–15k13 Nov
Fort Lauderdale → ChicagoFXE–PWK · Challenger 300/350 · 8 seats · ≈ 3h 00mEstimate $17k–32k16 Nov
Chicago → MiamiPWK–OPF · Cessna Citation Longitude · 12 seats · ≈ 3h 00mEstimate $14k–27k17 Nov
Nashville → ChicagoBNA–PWK · Cessna Citation CJ3 · 7 seats · ≈ 1h 20mEstimate $4k–8k19 Nov
Chicago → Kansas CityPWK–MKC · Bombardier Challenger 300 · 9 seats · ≈ 1h 20mEstimate $8k–14k19 Nov
Chicago → OmahaPWK–OMA · Cessna Citation XLS · 9 seats · ≈ 1h 20mOn request20 Nov
Kansas City → ChicagoMKC–PWK · Bombardier Challenger 300 · 9 seats · ≈ 1h 20mEstimate $8k–14k22 Nov
El Paso → ChicagoELP–PWK · LEAR 60 · 7 seats · ≈ 3h 10m$18,20029 Nov
Teterboro → ChicagoTEB–PWK · Citation Longitude · 9 seats · ≈ 2h 00mEstimate $10k–19k15 Dec
Pontiac → ChicagoPTK–PWK · Bombardier Challenger 604 · 12 seats · ≈ 55mEstimate $8k–15k18 Dec
Treasure Cay → ChicagoTCB–PWK · Citation V · 7 seats · ≈ 3h 20mEstimate $7k–13k22 Dec
Aspen → ChicagoASE–PWK · Cessna Citation XLS+ · 8 seats · ≈ 2h 45mEstimate $9k–17k26 Dec
Telluride → ChicagoTEX–PWK · Cessna Citation XLS+ · 8 seats · ≈ 2h 55mEstimate $10k–18k27 Dec
Chicago → AspenPWK–ASE · Cessna Citation XLS+ · 8 seats · ≈ 2h 45mEstimate $9k–17k30 Dec

Where Chicago/Prospect Heights/Wheeling empty legs fly

From Chicago/Prospect Heights/Wheeling to

Minneapolis12 legs
Woodruff12 legs
Indianapolis10 legs
Tucson8 legs
Omaha7 legs
Teterboro7 legs
Dallas6 legs
Bloomington4 legs

To Chicago/Prospect Heights/Wheeling from

Omaha9 legs
St Louis9 legs
Syracuse7 legs
Teterboro7 legs
Cleveland6 legs
Minneapolis6 legs
Naples5 legs
Pontiac5 legs

Aircraft seen

Cessna Citation XLS+46 legs
Bombardier Learjet 4533 legs
Bombardier Challenger 30020 legs
Embraer Praetor 50019 legs
Cessna Citation Bravo16 legs
Cessna Citation XLS16 legs
Dassault Falcon 200010 legs
LEAR 6010 legs

Counted from every empty leg JetsFly has listed to or from Chicago/Prospect Heights/Wheeling, including flights that have already departed. See also private jet charter in Chicago/Prospect Heights/Wheeling and all empty legs in United States.

Frequently asked questions

How much does an empty leg from Chicago cost?

Right now the 1 priced empty leg to or from Chicago start at $18,200 for the whole aircraft, not per seat. Empty legs usually cost well below a full charter of the same aircraft; the exact saving depends on the route and how close the flight is.

Where do empty legs from Chicago fly to?

The destinations we have seen most often are Minneapolis, Woodruff, Indianapolis, Tucson, Omaha. Routes change every day because each empty leg follows an aircraft's next charter.

How far ahead are empty legs from Chicago listed?

Most appear a few days to a few weeks before departure, when an operator knows where its aircraft has to be next. Dates and times can move with the main charter, so they suit travellers with some flexibility.

How do I book an empty leg?

Pick a flight with a price and press Book, or request one without a price and we confirm it with the operator. You book the whole aircraft, so bring everyone who fits in the seats shown.

Can I get told when a new empty leg from Chicago appears?

Yes. Set an empty leg alert and we e-mail you as soon as a matching flight is listed. You can set a maximum price and unsubscribe at any time.

Fly private from Chicago/Prospect Heights/Wheeling

Nearby cities, airports and destinations, with prices and empty legs.

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Empty legs in other cities

Las Vegas93 Teterboro90 Houston86 Toronto86 Lincoln71 Miami66 Dallas63 Van Nuys61 Calgary59 Fort Lauderdale40 Salt Lake City34 Palm Springs33

More from Chicago/Prospect Heights/Wheeling

Private jet charter in Chicago/Prospect Heights/Wheeling Turboprop charter in Chicago/Prospect Heights/Wheeling

Empty legs near Chicago/Prospect Heights/Wheeling

Chicago/West Chicago37 km Chicago39 km Kenosha54 km Gary68 km Milwaukee93 km Chicago/Rockford99 km