Empty Leg Flights From Chicago — 60 Live

Departing from Chicago (24 of 60)

• Sun, Aug 23
  (KPWK) Chicago, Illinois, United States→(KSTL) St Louis, Missouri, United States
  Cessna Citation CJ2
  $3,015
• Mon, Aug 24
  (KPWK) Chicago/Prospect Heights/Wheeling, Illinois, United States - Chicago Executive Airport→(KCID) Cedar Rapids, Iowa, United States - The Eastern Iowa Airport
  Embraer Praetor 500
  $4,853
• Mon, Aug 24
  (KMKE) Milwaukee, Wisconsin, United States - General Mitchell International Airport→(KIND) Indianapolis, Indiana, United States - Indianapolis International Airport
  Bombardier Learjet 60
  $6,400
• Mon, Aug 24
  (KDPA) Chicago/West Chicago, Illinois, United States - Dupage Airport→(KTYQ) Indianapolis, Indiana, United States - Indianapolis Executive Airport
  Cessna Citation Excel
  $3,333
• Mon, Aug 24
  (KJVL) Janesville, Wisconsin, United States - Southern Wisconsin Regional Airport→(KSJC) San Jose, California, United States - Norman Y. Mineta San Jose International Airport
  Beechcraft Hawker 800XP
  $20,624
• Mon, Aug 24
  (KENW) Kenosha, Wisconsin, United States→(KOMA) Omaha, Nebraska, United States
  Cessna Citation XLS
  $6,700
• Tue, Aug 25
  (KMKE) Milwaukee, Wisconsin, United States→(KLAS) Las Vegas, Nevada, United States
  Beechcraft Hawker 900XP
  $19,135
• Wed, Aug 26
  (KJVL) Janesville, Wisconsin, United States - Southern Wisconsin Regional Airport→(KBTV) Burlington, Vermont, United States - Burlington International Airport
  Beechcraft Hawker 800XP
  $10,400
• Wed, Aug 26
  (KMKE) Milwaukee, Wisconsin, United States→(KYIP) Detroit, Michigan, United States
  Beechcraft Hawker 900XP
  $3,838
• Thu, Aug 27
  (KMDW) Chicago, Illinois, United States - Chicago Midway International Airport→(KCLE) Cleveland, Ohio, United States - Cleveland Hopkins International Airport
  Beechcraft Hawker 800XP
  $17,688
• Thu, Aug 27
  (KMKE) Milwaukee, Wisconsin, United States→(KAZO) Kalamazoo, Michigan, United States
  Cessna Citation III
  $4,363
• Sat, Aug 29
  (KMKE) Milwaukee, Wisconsin, United States→(KGTF) Great Falls, Montana, United States
  Cessna Citation CJ4
  $15,210
• Sun, Aug 30
  (KARR) Chicago, Illinois, United States→(KBKL) Cleveland, Ohio, United States
  Dassault Falcon 900
  $7,320
• Sun, Aug 30
  (KMKE) Milwaukee, Wisconsin, United States→(KJPX) East Hampton, New York, United States
  Cessna Citation CJ4
  $11,273
• Sun, Aug 30
  (KGYY) Gary, Indiana, United States→(KFSD) Sioux Falls, South Dakota, United States
  Honda Aircraft HA-420 HondaJet
  $5,608
• Sun, Aug 30
  (KPWK) Chicago, Illinois, United States→(KTVC) Traverse City, Michigan, United States
  Dassault Falcon 50EX
  $6,956
• Mon, Aug 31
  (KMDW) Chicago, Illinois, United States→(KMBT) Murfreesboro, Tennessee, United States
  Pilatus PC 12
  $4,858
• Wed, Sep 2
  (C56) Monee, Illinois, United States→(KSMD) Fort Wayne, Indiana, United States
  Cirrus SR22
  $804
• Thu, Sep 3
  (KMKE) Milwaukee, Wisconsin, United States→(KAZO) Kalamazoo, Michigan, United States
  Cessna Citation III
  $4,580
• Fri, Sep 4
  (KORD) Chicago, Illinois, United States - Chicago O'Hare International Airport→(KMKC) Kansas City, Missouri, United States - Charles B. Wheeler Downtown Airport
  Bombardier Challenger 3500
  $16,114
• Fri, Sep 4
  (KMDW) Chicago, Illinois, United States→(KOPF) Miami, Florida, United States
  Bombardier Challenger 300
  $20,636
• Sun, Sep 6
  (KPWK) Chicago, Illinois, United States→(KSBM) Sheboygan, Wisconsin, United States
  Gulfstream G200
  $10,720
• Wed, Sep 9
  (KGYY) Gary, Indiana, United States→(KLOT) Chicago, Illinois, United States
  Cessna Citation XLS
  $6,164
• Wed, Sep 9
  (KLOT) Chicago, Illinois, United States→(KGYY) Gary, Indiana, United States
  Cessna Citation XLS
  $6,164

Frequently asked about Chicago empty legs

How many empty leg flights are available from Chicago?

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

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 25–75% below the equivalent retail charter rate. Discounts deepen as departure approaches, and the deepest discounts appear in the final 24 to 72 hours before departure, while 14-day-out inventory is closer to 35–40% off.

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.