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One way empty legs between Pittsburgh 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.
Pittsburgh International to Chicago Midway is about 350 nautical miles, and the eight listings here that publish a block time give one hour twelve or one hour eighteen minutes. Both cities spread their private traffic across several fields, and these nine legs use four of them.
Five of the nine legs are one Gulfstream G450 on five consecutive days. Aircraft Management Group listed a thirteen seat G450 from Pittsburgh International to Midway on 27, 28, 29 and 30 September and 1 October. That run is more than half of everything we have recorded on this corridor, and it is one aeroplane rather than five separate opportunities.
Take that run out and four legs remain, from four different operators. A Cessna Citation X from Hera Flight on 16 September, a Hawker 850XP from DuPage Aerospace on 18 September, a Cessna Citation XLS+ from Aircraft Management Group into O'Hare on 3 October, and a Bombardier Learjet 60 from Jetvia on 13 October. Those four are genuinely independent repositioning flights, and they are the reason this corridor is worth watching rather than the G450 week.
The airports matter more here than on most corridors. Seven legs ran Pittsburgh International to Midway, one ran Pittsburgh International to O'Hare, and one ran Allegheny County to DuPage, which is a different pair of fields at both ends. The computed distance on this page uses Pittsburgh International to Midway, the pair that seven of the nine actually used.
Nine legs on nine dates between 16 September and 13 October 2026, all of them inside four weeks. Five of those dates are the consecutive G450 run from 27 September to 1 October, so the corridor is thinner than nine legs in a month sounds.
Nothing on this corridor was live when this page was built. All nine have flown and not one was withdrawn. This corridor releases extremely late: the legs went on the board between nought and eleven days before departure, and five of the nine were listed on the morning of the day they flew. A corridor like this cannot be caught by checking the page, which is what the route alert below is for.
Approximate corridor between Pittsburgh and Chicago. Operators fly the sector direct; the airports each listing uses are shown on the flight itself.
Midway, O'Hare and DuPage are not interchangeable. Midway is the quickest into downtown Chicago, O'Hare is the airline hub and the slowest to get out of, and DuPage is business aviation only and well into the western suburbs. On a flight of an hour and a quarter the field you land at makes more difference to the day than the sector does.
Between 31 July and 17 October 2026 we recorded 9 empty legs from Pittsburgh to Chicago. One of them carried a published price, USD 8,400 for the whole aircraft on the Bombardier Learjet 60 that Jetvia listed for 13 October. Eight of the nine publish a block time, one hour twelve minutes on seven of them and one hour eighteen on the O'Hare leg, and all nine publish a seat count between seven and thirteen. None publishes a tail number.
| Departure | Aircraft | Seats | Operator's published price | Status |
|---|---|---|---|---|
| 16 Sep 2026 | Cessna Citation X | 8 | On request | Already flown |
| 18 Sep 2026 | Hawker 850XP | 8 | On request | Already flown |
| 27 Sep 2026 | Gulfstream G450 | 13 | On request | Already flown |
| 28 Sep 2026 | Gulfstream G450 | 13 | On request | Already flown |
| 29 Sep 2026 | Gulfstream G450 | 13 | On request | Already flown |
| 30 Sep 2026 | Gulfstream G450 | 13 | On request | Already flown |
| 01 Oct 2026 | Gulfstream G450 | 13 | On request | Already flown |
| 03 Oct 2026 | Cessna Citation XLS+ | 8 | On request | Already flown |
| 13 Oct 2026 | Bombardier Learjet 60 | 7 | USD 8,400 | Already flown |
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.
One of the nine legs carries a published price, USD 8,400 for a seven seat Bombardier Learjet 60 on 13 October, listed by Jetvia with a block time of one hour twelve minutes. That figure is for the whole aircraft exactly as the operator published it, and it is not a per seat fare or a from price.
The one published figure is not a rate for this route. A seven seat Learjet 60 is a much smaller aeroplane than the thirteen seat Gulfstream G450 that flew five of these legs, so USD 8,400 says what Jetvia asked for its own aircraft on one date in October and nothing at all about what the G450 week would have cost.
The other eight publish nothing on price, and that is their operators' practice rather than a comment on the corridor. Aircraft Management Group has six of them and publishes no figure on any of its 469 listings on this board across 283 city pairs. Hera Flight publishes none on any of its 508 and DuPage Aerospace none on any of its 74. Jetvia is the exception: it publishes a price on 2,134 of its 2,268 listings, which is why the single priced leg here is theirs.
Eight of the nine publish a block time and all nine publish a seat count, between seven and thirteen. Ask which Chicago field you are landing at, whether the departure time can still move, and what happens if the paid flight behind the positioning leg falls through.
Pittsburgh to Chicago empty legs are posted days ahead, not months. Leave your email and we watch both directions for you, Pittsburgh to Chicago and Chicago to Pittsburgh, and send you nothing else.