15Oct
Thu
Cessna Citation Excel/XLS Midsize jet, 9 seats
US$ 15,802
whole aircraft
Private jet from Naples to Chicago/West Chicago
We have seen 5 empty legs from Naples to Chicago/West Chicago, from US$ 15,802. A full charter is estimated at US$ 19,300–38,600. 998 nm, about 2h34 in the air.
- Distance
- 998 nm
- Flight time
- 2h34
- Typical empty leg, super-midsize jet
- US$ 24,690
- One-way charter, super-midsize jet
- US$ 38,600
Published flights
23Nov
Mon
Cessna Citation X Super-midsize jet, 9 seats
US$ 18,490
whole aircraft
27Dec
Sun
Gulfstream G280 Super-midsize jet, 10 seats
US$ 24,690
whole aircraft
Empty legs seen on this route
- Flights seen
- 5
- Lowest price
- US$ 15,802
- Median price
- US$ 19,790
- Latest flight
- 14 Oct 2026
Earlier flights
| 14 Oct 2026 | Gulfstream G280 | US$ 24,690 |
| 14 Oct 2026 | Hawker 125-700/800/850/900 | US$ 19,790 |
Prices are for the whole aircraft, converted to US dollars. Data from the public listings jetvega tracks.
What a full charter costs
| Class | Time | Hour | Charter |
|---|---|---|---|
| Turboprop, 8 seats | 3h58 | US$ 2,800 | US$ 11,100–US$ 22,200 |
| Very light jet, 4 seats | 3h20 | US$ 3,600 | US$ 12,000–US$ 24,000 |
| Light jet, 7 seats | 2h47 | US$ 4,800 | US$ 13,300–US$ 26,600 |
| Midsize jet, 8 seats | 2h40 | US$ 6,000 | US$ 16,000–US$ 32,000 |
| Super-midsize jet, 9 seats | 2h34 | US$ 7,500 | US$ 19,300–US$ 38,600 |
An empty leg on this route had a median price of US$ 24,690, against US$ 38,600 for a full charter on a super-midsize jet: about 36% less.
An estimate, not an offer: flight hours at the typical speed of the class × the average hourly rate. The lower figure applies when the aircraft is already in town; the higher one includes the aircraft flying back empty, which is how a one-way trip is usually priced. Airport fees not included.
Airports in Naples
- Southwest Florida International Airport RSW43 km from the centre
- Naples Municipal Airport APF0 km from the centre
- Page Field FMY49 km from the centre
- Marco Island Executive Airport MRK20 km from the centre
- Immokalee Regional Airport IMM48 km from the centre
Airports in Chicago/West Chicago
- Chicago O'Hare International Airport ORD30 km from the centre
- Chicago Midway International Airport MDW43 km from the centre
- Dupage Airport DPA0 km from the centre
- Chicago Executive Airport PWK37 km from the centre
- Aurora Municipal Airport AUZ24 km from the centre
Questions
How much is a private jet from Naples to Chicago/West Chicago?
A full charter runs about US$ 19,300–38,600 on a super-midsize jet (estimate). Empty legs on this route have been listed from US$ 15,802, with a median of US$ 19,790.
How long is the flight from Naples to Chicago/West Chicago?
It is 998 nautical miles (1,848 km): about 2h34 on a super-midsize jet, including take-off and landing.
Which aircraft fly Naples → Chicago/West Chicago?
Non-stop: turboprop (8 seats), very light jet (4 seats), light jet (7 seats), midsize jet (8 seats), super-midsize jet (9 seats). Seen on this route: Gulfstream G280, Cessna Citation Excel/XLS, Cessna Citation X, Hawker 125-700/800/850/900.
Are there empty legs from Naples to Chicago/West Chicago right now?
Yes, 3 listed now, from US$ 15,802. They are at the top of this page.
Which airports do the flights use?
In Naples: Southwest Florida International Airport (RSW), Naples Municipal Airport (APF), Page Field (FMY). In Chicago/West Chicago: Chicago O'Hare International Airport (ORD), Chicago Midway International Airport (MDW), Dupage Airport (DPA). Business jets often use smaller airports closer to where you are going.
What about the way back, Chicago/West Chicago to Naples?
Ask for a round trip in one request: the aircraft would fly back empty anyway, so it is usually cheaper than two one-way flights.
What is an empty leg?
It is a flight with no passengers on board: after dropping off a client the aircraft returns to base or repositions for the next trip. The operator sells that leg at a discount rather than fly it empty.