Empty leg flights to and from Chicago.
Empty leg flights from Chicago are discounted one-way private jet flights on aircraft repositioning out of Chicago Midway International Airport, Chicago Executive Airport. They typically cost 25–75% less than a standard charter. From Chicago, an empty leg to New York on a light jet is estimated at $1,700–$7,700, against $6,600–$10,300 for a full charter.
| Airports | Chicago Midway International Airport (MDW), Chicago Executive Airport (PWK) |
|---|---|
| Typical saving | 25–75% below standard charter |
| Routes with most empty legs | New York, Miami, Los Angeles, Toronto, Washington, D.C. |
| Empty legs on the board today | 0 |
| Market | United States · prices in USD |
Which airports do Chicago empty legs use?
Chicago Midway International Airport is the main private jet airport for Chicago on this site, with 1 other airport in range.
| Airport | Codes | Longest runway | Distance to centre | Type |
|---|---|---|---|---|
| Chicago Midway International Airport | KMDW / MDW | 1,988 m | 15 km | Airport with GA terminal |
| Chicago Executive Airport | KPWK / PWK | 1,524 m | 34 km | Business aviation terminal |
Runway lengths and coordinates from OurAirports (OurAirports open data (public domain), 2026); straight-line distances to the city centre use Wikidata coordinates (Wikidata (CC0), 2026).
Where do empty legs from Chicago usually go?
The corridors most likely to produce empty legs, judged by the size of the private jet market at each end, run from Chicago to New York, Miami, Los Angeles.
Estimates below use a light jet where it can fly the sector non-stop, otherwise the smallest category that can.
| Route | Distance | Block time | Empty leg (est.) | Charter (est.) |
|---|---|---|---|---|
| Chicago to New York | 618 nm | 1h 53m | $1,700–$7,700 | $6,600–$10,300 |
| Chicago to Miami | 1,035 nm | 2h 58m | $2,600–$12,300 | $10,400–$16,400 |
| Chicago to Los Angeles | 1,514 nm | 4h 14m | $3,700–$17,500 | $14,800–$23,300 |
| Chicago to Toronto | 379 nm | 1h 15m | $1,100–$5,200 | $4,400–$6,900 |
| Chicago to Washington, D.C. | 516 nm | 1h 36m | $1,400–$6,600 | $5,600–$8,800 |
| Chicago to Montreal | 646 nm | 1h 57m | $1,700–$8,000 | $6,800–$10,700 |
| Chicago to Dallas | 700 nm | 2h 05m | $1,800–$8,600 | $7,300–$11,500 |
| Chicago to Boston | 737 nm | 2h 11m | $1,900–$9,000 | $7,700–$12,000 |
| Chicago to Aspen | 889 nm | 2h 35m | $2,300–$10,700 | $9,100–$14,200 |
| Chicago to Las Vegas | 1,322 nm | 3h 44m | $3,300–$15,400 | $13,100–$20,500 |
| Chicago to San Francisco | 1,612 nm | 4h 29m | $3,900–$18,500 | $15,700–$24,700 |
| Chicago to London | 3,430 nm | 7h 42m | $17,400–$86,700 | $69,400–$115,600 |
Model estimate, not a quote. See how we calculate prices.
Which empty legs arrive into Chicago?
The largest private jet markets with modelled routes into Chicago are New York, Miami, Los Angeles, so those are the likeliest origins of an inbound empty leg.
| Route | Distance | Block time | Empty leg (est.) | Charter (est.) |
|---|---|---|---|---|
| New York to Chicago | 618 nm | 1h 53m | $1,700–$7,700 | $6,600–$10,300 |
| Miami to Chicago | 1,035 nm | 2h 58m | $2,600–$12,300 | $10,400–$16,400 |
| Los Angeles to Chicago | 1,514 nm | 4h 14m | $3,700–$17,500 | $14,800–$23,300 |
| Toronto to Chicago | 379 nm | 1h 15m | $1,100–$5,200 | $4,400–$6,900 |
| Washington, D.C. to Chicago | 516 nm | 1h 36m | $1,400–$6,600 | $5,600–$8,800 |
| Montreal to Chicago | 646 nm | 1h 57m | $1,700–$8,000 | $6,800–$10,700 |
| Dallas to Chicago | 700 nm | 2h 05m | $1,800–$8,600 | $7,300–$11,500 |
| Boston to Chicago | 737 nm | 2h 11m | $1,900–$9,000 | $7,700–$12,000 |
| Aspen to Chicago | 889 nm | 2h 35m | $2,300–$10,700 | $9,100–$14,200 |
| Las Vegas to Chicago | 1,322 nm | 3h 44m | $3,300–$15,400 | $13,100–$20,500 |
| San Francisco to Chicago | 1,612 nm | 4h 29m | $3,900–$18,500 | $15,700–$24,700 |
| London to Chicago | 3,430 nm | 7h 42m | $17,400–$86,700 | $69,400–$115,600 |
Model estimate, not a quote. See how we calculate prices.
How much does an empty leg from Chicago cost?
A light jet empty leg from Chicago is estimated at $900–$4,300 for a short sector and $2,100–$9,800 for a medium one.
The table models three sample distances: 300 nautical miles (about an hour in the air), 800 (about two hours) and 2,000 (five hours or more, beyond the range of the smallest categories).
| Aircraft category | 300 nm | 800 nm | 2,000 nm |
|---|---|---|---|
| Turboprop | $700–$3,300 | $1,700–$7,700 | Out of range |
| Very light jet | $800–$3,100 | $1,800–$7,100 | Out of range |
| Light jet | $900–$4,300 | $2,100–$9,800 | Out of range |
| Midsize jet | $1,300–$6,000 | $2,800–$13,200 | $6,400–$30,800 |
| Super-midsize jet | $1,900–$8,300 | $3,900–$17,100 | $9,000–$39,600 |
| Heavy jet | $2,300–$11,300 | $4,500–$22,400 | $10,400–$51,800 |
| Ultra-long-range jet | $3,500–$16,500 | $6,700–$31,700 | $15,500–$72,900 |
Model estimate, not a quote. See how we calculate prices.
How do I book an empty leg from Chicago?
Tell us your route and how flexible you are; we check the flights operators have released and confirm the one that fits.
- Send the route, dates you could travel and passenger numbers using the form below, or set up an alert.
- We check repositioning flights from licensed operators and price a standard charter for comparison.
- You choose. We confirm the flight with the operator and name the operating carrier and aircraft on the quote before you pay.
Questions about Chicago empty legs
Which airports do empty legs from Chicago use?
Chicago Executive Airport handle most business aviation in Chicago; Chicago Midway International Airport also have general aviation terminals. The operator chooses the airport the aircraft is already at.
How much does an empty leg from Chicago cost?
On a light jet, estimates run from $900 for a short sector of about 300 nautical miles to $9,800 for one of about 800. These are model estimates, not quotes; listed flights show the operator’s price plus our fee.
How far in advance are empty legs available?
Most appear between a few days and about two weeks before departure, because they depend on other bookings being confirmed. Some are published 24–48 hours ahead.
Can an empty leg flight be cancelled?
Yes. An empty leg exists only because of another customer’s booking. If that customer changes date or route, or cancels, the empty leg may be rescheduled or withdrawn. Refund terms are set out in your charter agreement, and consequential costs such as hotels or replacement flights are not normally covered. Check the terms before you pay. No audited industry cancellation rate is published.
Do you pay per seat or for the whole aircraft?
Almost always the whole aircraft. An empty leg on an eight-seat jet costs the same for one passenger or eight, which is why empty legs work best for groups. A few operators and apps sell single seats on selected flights; where that applies, the listing says so.
Sources
- OurAirports open data (public domain), 2026-09-20 (accessed 2026-09-20). Airport codes, coordinates, elevation and runway lengths.
- Wikidata (CC0), 2026-09-20 (accessed 2026-09-20). City-centre coordinates used for airport-to-city distances.
- Paramount Business Jets, "Private Jet Rental | Jet Cost & Hourly Rates (2026)", 2026-08 (accessed 2026-09-20)
- Amalfi Jets, "Private Jet Cost Per Hour 2026: Rates by Jet Type", 2026-06-15 (accessed 2026-09-20)
- Jetvice, "Private Jet Charter Hourly Rates 2026", 2026-09-01 (accessed 2026-09-20)
- Business Travel Executive, "Empty Legs, Empty Promises?", 2023-02-02 (accessed 2026-09-20). XO estimate that 30–50% of the charter fleet often flies empty; Victor on savings of up to 75%; Chapman Freeborn on change and cancellation risk.
- European Central Bank euro foreign exchange reference rates (via frankfurter.dev), 2026-09-18 (accessed 2026-09-20). Rates used for USD, EUR and GBP conversions.
Last reviewed 20 September 2026 by Empty Leg Exclusive Editorial Team.
Flying from Chicago? Tell us when.
Give us your route and dates. We will send you the empty legs that fit and a charter price for comparison.
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