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Empty leg flights to Chicago

2 empty legs (1 listed or confirmed in the last 5 days)

Chicago airports: MDW, ORD, PWK, DPA · prices include our fee · operators confirm availability before you’re quoted

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Free · stop any time · nearby airports included

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Alerts need a departure — use the search on the home page to set one for flights into Chicago.

Representative Citation CJ3 — not the actual aircraft
NewWed 7 OctConfirmed 11h ago
West Palm BeachChicago
Textron AviationCitation CJ3Light jet
982 nm · ~2 h 45 min
  • Starlink Wi-Fi

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Typical charter $12k–$23k · est.

Representative GIV-SP — not the actual aircraft
Thu 15 Oct – Fri 16 OctMay be gone
Fort LauderdaleChicago
GulfstreamGIV-SPHeavy jet
1,024 nm · ~2 h 30 minBuilt 2002 · refurb. 2026
  • Starlink Wi-Fi

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Typical charter $26k–$49k · est.

Where they fly in from

Airports

  • Chicago Midway International Airport (MDW / KMDW)
  • Chicago O'Hare International Airport (ORD / KORD)
  • Chicago Executive Airport (PWK / KPWK)
  • Dupage Airport (DPA / KDPA)

Nearby: Gary (GYY), Valparaiso (VPZ), Michigan City (MGC), Kankakee (IKK), Kenosha (ENW)

Empty legs from Chicago

Questions

How do empty leg flights to Chicago work?

An empty leg is a private jet flying to Chicago without passengers — usually on its way to or from another charter. Operators offer these flights for less than a normal charter. Prices on this page are for the whole aircraft, not per seat, and every leg is subject to the operator's main trip going ahead.

Which Chicago airports do they fly into?

We count legs at Chicago Midway International Airport (MDW), Chicago O'Hare International Airport (ORD), Chicago Executive Airport (PWK), Dupage Airport (DPA). Legs at nearby airports are listed separately below.

How much does an empty leg to Chicago cost?

Most operators share empty-leg prices on request. Request a leg — we reply in minutes and send your quote for the whole aircraft as soon as the operator confirms.

How far ahead are empty legs available?

Most are posted a day or two before departure, and they go quickly. Set an alert on this page and we'll email you when a new one is listed.

What if the flight I want isn't listed?

Request the flight you need. We'll look for an empty leg or a well-priced charter and send you a quote — free, with no obligation.

What happens if the operator cancels the leg?

An empty leg exists because of the operator's main trip, so it can change or be cancelled if that trip does. If a leg you booked is cancelled by the operator, you receive a credit for a future flight, valid 12 months, as set out in our booking terms.

New to empty legs? Read the empty leg guide.