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One way empty legs between Naples, Florida and Chicago, 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.
Naples to Chicago is about 1,005 nautical miles between Naples Municipal and Chicago Executive, the pairing that carries more of this corridor than any other, and the legs that publish a block time run from two hours 42 to three hours 18. Southwest Florida is a second home market for the Midwest, and the aircraft that bring owners down have to get back.
Chicago is the biggest thing Naples does, by a factor of two and a half. Naples sends 27 recorded movements to Chicago. The next biggest destination is Dallas at eleven, then Teterboro and Venice at seven each. From the other end the two cities are first for each other: Chicago takes 27 recorded arrivals from Naples and sixteen from Teterboro, which is the next biggest origin.
The return journey is a third of the size. Chicago back to Naples is ten recorded legs against these 27. Aircraft go north and find their own way back, which is the condition that fills a corridor with empty legs in one direction.
Three operators run this corridor and each one uses its own Chicago field. DuPage Aerospace flies ten legs and every one of them lands at DuPage. Elite Jets flies fourteen and lands at Chicago Executive, Midway and Rockford but never at DuPage. Jetvia flies three, to O'Hare and Chicago Executive. So the operator effectively decides which side of Chicago you arrive on, and the five fields are not interchangeable.
Twenty seven movements on 21 dates, departing between 12 September 2026 and 3 January 2027. The weight is in October: seventeen of the 27 depart that month, against eight in September and two over Christmas and New Year.
Two were still on the board when this page was built, the 31 October Jetvia Learjet 60 and the 3 January Elite Jets Phenom 300. The other 25 have either flown or come off the board, and that churn is the honest shape of this corridor: it produces a lot of listings and they do not sit around. Notice is generous by the standards of this site, most legs first appearing three to six weeks before departure, so the route alert is worth more than checking the page daily.
Approximate corridor between Naples and Chicago. Operators fly the sector direct; the airports each listing uses are shown on the flight itself.
Five fields at one end is the thing to watch on this route. Chicago Executive and DuPage are on opposite sides of the metropolitan area and are an hour apart in traffic. Rockford matters more: it is filed as Chicago in the listings and it is about 78 miles from the Loop, which is a drive of well over an hour, so the two Elite Jets legs that land there are a different proposition from the ones landing at Chicago Executive. Ask which field before anything else. Two counts on this page need explaining rather than hiding. The table below lists 29 rows for 27 flights, because the 4 October Jetvia Learjet 60 and the 14 October DuPage Gulfstream G-280 were each listed twice, weeks apart, and we show the feed as it stands rather than quietly dropping a row. The 31 October Jetvia leg is also filed as a Learjet 60XR in the live record and as a Learjet 60 in the archive, which is why the type count in the table reads one higher than the seven types named on this page.
Reading the record.
| Departure | Aircraft | Seats | Operator's published price | Status |
|---|---|---|---|---|
| Reading the record. | ||||
Every leg we have recorded between Naples and Chicago, 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.
Three of the 27 flights carry a published price and all three are Jetvia, all three at USD 16,300 for the whole aircraft on a seven seat Learjet 60. They appear as four of the 29 rows in the table below, because one of them was listed twice. That is one figure repeated across three different airframes on three different dates, so read it as this operator's rate for the sector rather than as a market price for the corridor.
The other 24 flights publish nothing, and the reason is operator policy rather than anything about this route. DuPage Aerospace has published a figure on none of its 77 recorded listings and Elite Jets on none of its 170. Jetvia is the opposite case, publishing on 1,993 of its 2,101, but its entire feed carries a single aircraft type, so its figures tell you about one Learjet 60 operation and not about the corridor.
What you can compare is the cabin, and it is narrow: every one of the 27 legs seats seven to ten. Twelve are an eight seat Embraer Phenom 300, five a ten seat Gulfstream G-280, five Hawkers at eight, three Learjet 60s at seven and two Gulfstream G200s at nine. There is no light jet and nothing above ten seats on the whole corridor.
One cluster to read carefully. A single DuPage Aerospace Gulfstream G-280 accounts for five of the 27, on 30 September and 8, 9, 14 and 15 October. That is one airframe on a repeating pattern, not five independent chances. Ask the operator which Chicago field you are landing at, whether the departure time can still move, and what happens if the paid flight that created this empty leg falls through.
Naples to Chicago empty legs are posted days ahead, not months. Leave your email and we watch both directions for you, Naples to Chicago and Chicago to Naples, and send you nothing else.