Empty Leg Flights From Chicago — 73 Live

Departing from Chicago (24 of 73)

• Wed, Oct 7
  (KPWK) Chicago, Illinois, United States→(KGPZ) Grand Rapids, Minnesota, United States
  Cessna Citation CJ2
  $5,584
• Wed, Oct 7
  (KMKE) Milwaukee, Wisconsin, United States→(KBOS) Boston, Massachusetts, United States
  Bombardier Learjet 60
  $14,472
• Thu, Oct 8
  (KMKE) Milwaukee, Wisconsin, United States - General Mitchell International Airport→(KPTK) Pontiac, Michigan, United States - Oakland County International Airport
  Cessna Citation X
  $5,856
• Thu, Oct 8
  (KGYY) Gary, Indiana, United States→(KGRR) Grand Rapids, Michigan, United States
  Honda Aircraft HA-420 HondaJet
  $3,293
• Thu, Oct 8
  (KJVL) Janesville, Wisconsin, United States - Southern Wisconsin Regional Airport→(KANE) Minneapolis, Minnesota, United States - Anoka County-Blaine (Janes Field) Airport
  Beechcraft Hawker 800XP
  $4,671
• Thu, Oct 8
  (KARR) Chicago, Illinois, United States→(KSUS) St Louis, Missouri, United States
  Dassault Falcon 900
  $7,260
• Thu, Oct 8
  (KDPA) Chicago, Illinois, United States→(KFWA) Fort Wayne, Indiana, United States
  Pilatus PC 12 NG
  $2,354
• Thu, Oct 8
  (KMDW) Chicago, Illinois, United States→(KOPF) Miami, Florida, United States
  Bombardier Global 5000
  $33,323
• Fri, Oct 9
  (KPWK) Chicago/Prospect Heights/Wheeling, Illinois, United States - Chicago Executive Airport→(KPDC) Prairie Du Chien, Wisconsin, United States - Prairie Du Chien Municipal Airport
  Bombardier Challenger 300
  $6,968
• Fri, Oct 9
  (KMDW) Chicago, Illinois, United States→(KIAD) Dulles, Virginia, United States
  Cessna Citation CJ4
  On Request
• Sat, Oct 10
  (KUES) Waukesha, Wisconsin, United States→(KHCR) Heber, Utah, United States
  Cessna Citation CJ4
  $14,598
• Sun, Oct 11
  (KLOT) Chicago/Romeoville, Illinois, United States - Lewis University Airport→(KHPN) White Plains, New York, United States - Westchester County Airport
  Cessna Citation III
  $11,050
• Sun, Oct 11
  (KUES) Waukesha, Wisconsin, United States→(KGPI) Kalispell, Montana, United States
  Cessna Citation CJ4
  $15,958
• Mon, Oct 12
  (KGYY) Gary, Indiana, United States→(KSUE) Sturgeon Bay, Wisconsin, United States
  Cessna Citation XLS
  $6,164
• Mon, Oct 12
  (KARR) Chicago, Illinois, United States→(KMCI) Kansas City, Missouri, United States
  Dassault Falcon 900
  $7,779
• Tue, Oct 13
  (KUES) Waukesha, Wisconsin, United States→(KAUS) Austin, Texas, United States
  Cessna Citation CJ4
  $13,458
• Tue, Oct 13
  (KMDW) Chicago, Illinois, United States→(KDJT) West Palm Beach, Florida, United States
  Bombardier Challenger 350
  $25,607
• Wed, Oct 14
  (KUES) Waukesha, Wisconsin, United States→(KTEB) Teterboro, New Jersey, United States
  Gulfstream V
  $29,313
• Thu, Oct 15
  (KPWK) Chicago/Prospect Heights/Wheeling, Illinois, United States - Chicago Executive Airport→(KMSP) Minneapolis, Minnesota, United States - Minneapolis-St Paul International/Wold-Chamberlain Airport
  Embraer Praetor 500
  $6,586
• Thu, Oct 15
  (KPWK) Chicago/Prospect Heights/Wheeling, Illinois, United States - Chicago Executive Airport→(KTYQ) Indianapolis, Indiana, United States - Indianapolis Executive Airport
  Bombardier Challenger 300
  $6,794
• Thu, Oct 15
  (KMDW) Chicago, Illinois, United States→(KCAK) Akron, Ohio, United States
  Dassault Falcon 2000
  $8,442
• Thu, Oct 15
  (KENW) Kenosha, Wisconsin, United States→(KFTW) Fort Worth, Texas, United States
  Cessna Citation CJ4
  $11,868
• Fri, Oct 16
  (KPWK) Chicago/Prospect Heights/Wheeling, Illinois, United States - Chicago Executive Airport→(CYOW) Ottawa, Ontario, Canada - Ottawa Macdonald-Cartier International Airport
  Bombardier Challenger 300
  $16,375
• Fri, Oct 16
  (KORD) Chicago, Illinois, United States→(KCXY) Harrisburg, Pennsylvania, United States
  Cessna Citation CJ2
  $7,914

Frequently asked about Chicago empty legs

How many empty leg flights are available from Chicago?

73 live empty leg flights departing from Chicago today on SkyAccess, sourced from certified charter operators repositioning aircraft through the Chicago metro cluster. Inventory updates throughout the day.

What airports serve Chicago empty leg flights?

Primary GA airport: Chicago Executive (KPWK). SkyAccess searches a 80-mile radius around the primary airport to catch every charter-friendly field in the Chicago metro cluster — so this page surfaces empty legs from all IL GA airports within range.

How much can I save flying empty leg from Chicago?

Typical empty leg pricing from Chicago runs 25 to 75% below a comparable full charter. Operators can set a listing's price to step down as departure approaches, so the same leg can cost less in the final 24 to 72 hours than it did two weeks out.

When should I book an empty leg from Chicago?

For the deepest discount, search within 24–72 hours of departure. Inventory peaks Wednesday through Friday on most IL corridors. Set saved-search alerts on the KPWK radius to catch new listings as they publish.