Private jet hire · Illinois
Chicago Private jet hire Chicago: live empty legs, up to 75% less
Live empty legs to and from Chicago’s business-aviation airports: Midway, Chicago Executive, DuPage and O’Hare. Search your dates, or request a confirmed quote.
Live empty legs to and from Chicago’s business-aviation airports: Midway, Chicago Executive, DuPage and O’Hare. Search your dates, or request a confirmed quote.
Live prices, sourced from the global empty-leg marketplace. Empty legs reprice and vanish by the minute — get a live quote before yours reposts.
Set an alert and we’ll email you the moment one appears. Around 95% of legs don’t match a first search — they come and go daily, so watching a route is how most people actually fly one.
Flying both ways? Book any leg and we’ll find or pair your return — plus transfers, catering, pets in the cabin and the full itinerary, handled end to end.
Legs into Chicago come from New York, Texas and the west, as aircraft reposition across the country.
An empty leg is a private jet flying without passengers, usually to get back to base or to its next booking. Because the operator is flying anyway, the aircraft is offered for up to 75% less than chartering it in the usual way. Whether you call it private jet hire, private jet rental or charter, the board above shows every live leg touching Chicago’s business-aviation airports.
Four airports matter. Midway (MDW) is the closest to the Loop. Chicago Executive (PWK) and DuPage (DPA) are the business-aviation fields to the north-west and west, and O’Hare (ORD) takes long-range and heavy jets. Each has at least one private terminal (FBO) on the general-aviation side, where you check in and board without going near the airline halls.
Distances are from airport directories, not road distances. Drive times change sharply in rush hour on the Kennedy, the Eisenhower and the Dan Ryan, and your FBO can arrange a car to meet the aircraft.
Sources: CBP Midway fact sheet; FltPlan, Chicago Executive; ACUKWIK, DuPage; FltPlan, O’Hare.
Indicative charter rates by aircraft class, sourced from the global empty-leg marketplace. Empty legs are the bargain when your dates match.
About 9 miles south-west of the city, Midway is the obvious choice for downtown, the South Loop and McCormick Place. It has two FBOs: Atlantic Aviation on South Laramie Avenue and Signature on South Central Avenue. Its longest runway is 6,522 ft, which suits light, midsize and super-midsize jets; the operator confirms whether a larger aircraft can use it. International arrivals clear customs plane-side: a CBP officer meets the aircraft at the FBO, and the pilot must request permission to land at least 24 hours before arrival. Published hours are 08:00 to midnight, seven days a week (CBP Midway fact sheet).
Chicago Executive, in Wheeling, is about 18 miles north-west of the city. It is the old Palwaukee airport. There are three FBOs: Atlantic Aviation, Signature and Hawthorne Global Aviation Services. The longest runway is 5,001 ft, so this is light and midsize jet territory. For international arrivals, ask your operator about customs. Ground engine runs are banned between 22:00 and 07:00 and the field sits among noise-sensitive housing, so check with the operator before you plan a very late departure.
About 29 miles west of the city in West Chicago, DuPage is run by its own airport authority and has a 24-hour control tower. Its main runway is 7,571 ft, long enough for most business jets, and the single FBO is DuPage Flight Center. It is handy for Naperville, Oak Brook and the western suburbs. For international arrivals, ask your operator about customs.
O’Hare is about 14 miles north-west of the city, with a 13,000 ft runway. Private flights use the one FBO, Signature, on Patton Road. It has customs landing rights and suits heavy jets on long-range or international trips. The limits are the ones you would expect at a major airline hub: a landing fee, noise-abatement procedures from 22:00 to 07:00, and charter operators asked to contact Signature about security rules before departure (FltPlan, O’Hare).
With an empty leg, it is the one the operator has listed. When you are choosing between two legs, or pricing a full charter, a few rules of thumb help.
Legs from the middle of the country run in every direction, and the destinations change from day to day, so the best way to read them is the board itself. New York is the obvious business route; our page on private jet hire New York covers Teterboro and the other airports at that end.
If you are flexible, Texas is worth a look: see private jet hire Houston, Dallas private jet hire and our wider Texas page.
Further west, Las Vegas and Denver are common stops for aircraft repositioning across the country. For the national picture, read our guide to empty leg flights in the USA.
The mix of aircraft shifts as fleets reposition, so set a route alert as well as checking the board. Once someone enquires, the booking decision on an empty leg is usually made within a day or two, sometimes the same day.
An empty leg is priced for the whole aircraft, not per seat. Fill the seats and the cost per person falls with each passenger. Most of the spread in price is aircraft size and distance: a light jet on a short hop sits at the bottom, a heavy jet on a coast-to-coast run at the top. Every price on the board follows the currency picker, so you can compare in dollars, pounds or euros.
US domestic flights also carry federal tax: 7.5% of the fare plus $5.30 per passenger per segment (FAA aviation excise tax rates). Your confirmed quote shows what applies.
For hourly rates by aircraft size, see private jet rental costs by class and our guide to private jet charter cost. If no leg fits, the “Didn’t find your leg?” tool below prices a full charter on your route in seconds.
Chicago legs follow the city’s calendar. Most weeks they are repositioning flights: aircraft that brought business travellers in on Monday heading home, or jets from Chicago-based fleets going out to collect passengers. We expect more legs in event and convention weeks, when aircraft drop passengers, leave empty and come back empty to collect them.
These patterns are our reading of how event traffic behaves, not a promise of supply. Elsewhere in the US, the Las Vegas Grand Prix in November is another event that moves aircraft.
Snow and ice mostly add time on the ramp. At O’Hare the normal first measurable snow falls around 18 November and the last around 2 April, with inch-plus days normal from about 7 December to 20 March (NWS Chicago, 30-year normals). In that window, expect de-icing before departure.
De-icing means spraying the aircraft with heated fluid to clear ice, then often an anti-icing fluid to stop it re-forming before take-off. Atlantic Aviation at Chicago Executive lists Type I and Type IV fluids, and the airport has heated hangars that take aircraft up to Global Express size (FltPlan). Ask whether de-icing is included in your quote.
Winter weather can also move an empty leg, because the operator’s own schedule comes first. Read what happens if an empty leg is cancelled or delayed before you build a trip around one. Most legs are listed days rather than weeks ahead, so our guide on how to find empty legs explains why a route alert beats checking the board each morning.
The full walk-through is in how to book an empty leg. Empty legs fly the same aircraft, crew and operator certificate as a full-price charter; for the detail, see are empty legs safe?
Chicago’s board changes every day, and some days nothing matches your route. Save a free route alert for Chicago and where you want to go and we’ll email you when a matching leg is listed, or price a full charter on your dates below.
How empty legs work, what private hire really costs, and flying Chicago for less.
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Tell us your route and your email. The moment a matching empty leg appears on the live feed, it lands in your inbox — often days, sometimes hours, before it sells.