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One way empty legs between Chicago and Naples, Florida, exactly as the operators list them. The operator confirms availability and the price with you directly.
Straight line distance between the two cities. Actual routing and flight time depend on the aircraft and the airports.
Chicago to Naples is about 1,005 nautical miles between Chicago Executive and Naples Municipal, and the legs that publish a block time run three hours flat to three hours six. Southwest Florida is a second home market for the Midwest, and this is the outbound half of that traffic.
This is the quiet direction, and that is the single most useful thing to know about it. Naples back to Chicago is 27 recorded legs against these ten. The same corridor produces nearly three times as many empty legs northbound as southbound, because the aircraft that fly owners down to Florida are repositioning home rather than going down empty.
Three operators account for all ten, and they are not comparable. Elite Jets flies five, all of them an eight seat Embraer Phenom 300 out of Chicago Executive. DuPage Aerospace flies three out of DuPage, two on a Hawker 850XP and one on a Gulfstream G-280. Call a Jet supplies the last two, a nine seat Citation Excel in early August, and those two rows carry no airport code at either end, so they record that something flew the corridor and not where from or to.
The same two DuPage airframes work both directions. The Hawker 850XP and the Gulfstream G-280 on these southbound legs are the same tail numbers that appear on the Naples to Chicago page. That is what a genuine two way repositioning pattern looks like, rather than two unrelated feeds that happen to share a city.
Ten movements on ten dates, departing between 5 August 2026 and 6 May 2027, and the distribution is lumpy rather than regular. Two in early August, three in September, one in October, three in a single week in December and one in May.
Two were still on the board when this page was built, the 9 December and the 6 May Elite Jets Phenom 300s. Ten legs across nine months is a trickle, not a schedule, so the route alert is the sensible way to catch the next one. Notice here can be very long: the 6 May 2027 leg was first listed on 8 September 2026, eight months ahead.
Approximate corridor between Chicago and Naples. Operators fly the sector direct; the airports each listing uses are shown on the flight itself.
Chicago Executive and DuPage are an hour apart in Chicago traffic and which one you leave from is decided by which operator has the leg: Elite Jets runs Chicago Executive, DuPage Aerospace runs DuPage. The two Call a Jet legs in August name no field at either end, which is why the airport counts above add to eight rather than ten. Those two are also filed under Naples Florida rather than Naples in our record, so they sit in a different bucket from the other eight even though they are the same city. One more count needs explaining: the table below lists eleven rows for ten flights, because the 16 December Elite Jets Phenom 300 was listed twice, two weeks apart.
Reading the record.
| Departure | Aircraft | Seats | Operator's published price | Status |
|---|---|---|---|---|
| Reading the record. | ||||
Every leg we have recorded between Chicago and Naples, in either direction, since 30 July 2026, whether it is still on the board or not. A leg leaves the board when the operator stops publishing it, and we cannot tell from outside whether it was sold or withdrawn, so these are counts of what was listed, not of what flew.
One bar per calendar month, from the first month in our record to the furthest date an operator has published so far. Grey bars are months already past, gold is this month and the months ahead. A blank month is a month we have no record for, and before August 2026 that means we were not yet recording. The months ahead hold only what operators have published up to now, and most empty legs appear days or weeks before departure, so those bars will keep growing. The shape says how far ahead operators publish, not how busy a month will be.
| Airports flown | Legs recorded | On the board | Priced | Last seen | |
|---|---|---|---|---|---|
| Reading the record. | |||||
Each row is a pair of airports as the operator named them, in the direction flown. Both directions of the corridor are counted. An operator that names only the city leaves us the city, which is why some rows are city names.
The price on a card is the operator's figure for the whole aircraft. What that comes to per seat, across every type we see, is in how much an empty leg private jet costs.
Not one of the ten legs carries a published price. That is operator policy rather than anything about this route: Elite Jets has published a figure on none of its 170 recorded listings, DuPage Aerospace on none of its 77 and Call a Jet on none of its 214. That is 461 listings between the three of them without a price.
So nothing on this page can be compared on cost and we show nothing rather than guess. The figure comes from the operator when you ask, and on a three hour sector the whole aircraft figure is the first thing worth asking for.
What you can compare is the cabin, and the choice is narrow: five of the ten are the same eight seat Embraer Phenom 300, two are a nine seat Citation Excel, two an eight seat Hawker 850XP and one a ten seat Gulfstream G-280. Every leg publishes a seat count and they run eight to ten.
Two cautions rather than one. The five Elite Jets legs are the same aircraft on the same route, but four publish a block time of three hours six and the 6 May 2027 leg publishes three hours flat, and we show the feed as it stands. The two Call a Jet rows deserve more care: across its 214 listings Call a Jet names 47 different aircraft types and carries no airport code on a single row, so read those two as a record that a Citation Excel flew and not as a specification. Ask the operator which Chicago field you are leaving from, whether the departure time can still move, and what happens if the paid flight that created this empty leg falls through.
Chicago to Naples empty legs are posted days ahead, not months. Leave your email and we watch both directions for you, Chicago to Naples and Naples to Chicago, and send you nothing else.