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Search future private jet repositioning flights by origin, destination, aircraft category, departure window, and published price. Open a listing to request operator confirmation and final pricing.
2,606 current listings Verified Jul 15, 2026, 4:40 AM UTCView market activityDeparture calendarDestination finderAircraft categoriesLive price indexBest value dealsRoute alerts
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27 matching flights
| Route | Departure | Aircraft | Seats | Published price | |
|---|---|---|---|---|---|
| Chicago (KMDW) to Washington (KIAD) | July 15, 2026, 07:00 | Bombardier Learjet 60Midsize jet | 7 | $7,920 | |
| Chicago (KMDW) to Washington (KIAD) | July 15, 2026, 07:00 | Bombardier Learjet 60Midsize jet | 8 | $8,580 | |
| Chicago (KMDW) to Missoula (KMSO) | July 16, 2026, 07:00 | Bombardier Challenger 605Heavy jet | 10 | $29,060 | |
| Chicago (KMDW) to Houston (KHOU) | July 16, 2026, 07:00 | Cessna Citation XLSMidsize jet | 9 | $14,730 | |
| Chicago (KMDW) to Houston (KHOU) | July 17, 2026, 07:00 | Gulfstream G200Super midsize jet | 8 | $16,490 | |
| Chicago (KMDW) to Sioux Falls (KFSD) | July 18, 2026, 07:00 | Bombardier Learjet 60Midsize jet | 7 | $9,900 | |
| Chicago (KMDW) to Sioux Falls (KFSD) | July 18, 2026, 07:00 | Bombardier Learjet 60Midsize jet | 8 | $10,780 | |
| Chicago (KMDW) to Sioux Falls (KFSD) | July 18, 2026, 07:00 | Bombardier Learjet 60Midsize jet | 8 | $10,780 | |
| Chicago (KMDW) to Sioux Falls (KFSD) | July 18, 2026, 07:00 | Bombardier Learjet 60Midsize jet | 7 | Request quote | |
| Chicago (KMDW) to Sioux Falls (KFSD) | July 18, 2026, 07:00 | Bombardier Learjet 60Midsize jet | 7 | $9,900 | |
| Chicago (KMDW) to Sioux Falls (KFSD) | July 18, 2026, 07:00 | Bombardier Learjet 60Midsize jet | 8 | $10,780 | |
| Chicago (KMDW) to Sioux Falls (KFSD) | July 18, 2026, 07:00 | Bombardier Learjet 60Midsize jet | 7 | $9,900 | |
| Chicago (KMDW) to Sioux Falls (KFSD) | July 18, 2026, 07:00 | Bombardier Learjet 60Midsize jet | 8 | $10,780 | |
| Chicago (KMDW) to Sioux Falls (KFSD) | July 18, 2026, 07:00 | Bombardier Learjet 60Midsize jet | 7 | $9,900 | |
| Chicago (KMDW) to Sioux Falls (KFSD) | July 18, 2026, 07:00 | Bombardier Learjet 60Midsize jet | 8 | $10,780 | |
| Chicago (KMDW) to Denver (KBJC) | July 19, 2026, 07:00 | Bombardier Learjet 60Midsize jet | 7 | $16,500 | |
| Chicago (KMDW) to Denver (KBJC) | July 19, 2026, 07:00 | Bombardier Learjet 60Midsize jet | 8 | $17,930 | |
| Chicago (KMDW) to Trenton (KTTN) | July 26, 2026, 07:00 | Bombardier Learjet 60Midsize jet | 7 | $9,240 | |
| Chicago (KMDW) to Cleveland (KCLE) | July 26, 2026, 07:00 | Bombardier Learjet 60Midsize jet | 7 | $5,280 | |
| Chicago (KMDW) to Trenton (KTTN) | July 26, 2026, 07:00 | Bombardier Learjet 60Midsize jet | 8 | $10,010 | |
| Chicago (KMDW) to St Louis (KSTL) | July 27, 2026, 07:00 | Bombardier Learjet 60Midsize jet | 7 | $5,940 | |
| Chicago (KMDW) to St Louis (KSTL) | July 27, 2026, 07:00 | Bombardier Learjet 60Midsize jet | 7 | $5,940 | |
| Chicago (KMDW) to Miami (KOPF) | September 5, 2026, 07:00 | Bombardier Challenger 300Super midsize jet | 9 | $15,840 | |
| Chicago (KMDW) to El Paso (KELP) | September 23, 2026, 07:00 | Bombardier Learjet 60Midsize jet | 7 | $21,120 | |
| Chicago (KMDW) to El Paso (KELP) | September 23, 2026, 07:00 | Bombardier Learjet 60Midsize jet | 8 | $22,880 | |
| Chicago (KMDW) to Cahokia/St Louis (KCPS) | February 19, 2027, 07:00 | Bombardier Challenger 850Heavy jet | 15 | $31,560 | |
| Chicago (KMDW) to Minneapolis (KMSP) | March 29, 2027, 07:00 | Bombardier Challenger 850Heavy jet | 15 | $31,560 |
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