PrivateJetSky / Routes / New York to Chicago
New York to Chicago by private jet
The classic business day trip: 640 nm, under two hours in anything with turbines, Midway’s FBOs ten minutes from the Loop. This route is where the turboprop and very-light-jet classes earn their keep. The block-time penalty versus a heavy is minutes; the invoice difference is thousands.
Cost by aircraft class EST
| Class | Typical aircraft | Block time | One-way, all-in |
|---|---|---|---|
| Turboprop | Pilatus PC-12 NGX | 2h 41m | $5.7K–$10K |
| Very light jet | Embraer Phenom 100EV | 2h 02m | $5,288–$8,172 |
| Light jet | Embraer Phenom 300E | 1h 50m | $7.1K–$11K |
| Midsize jet | Cessna Citation XLS Gen2 | 1h 55m | $10K–$15K |
| Super-midsize | Bombardier Challenger 3500 | 1h 49m | $13K–$19K |
| Large cabin | Bombardier Challenger 650 | 1h 49m | $18K–$27K |
| Ultra-long-range | Bombardier Global 6000 | 1h 46m | $26K–$42K |
Assumes 4 passengers, spot-market rates, and the two-hour daily billing minimum where the leg is shorter. Positioning, meaning where the aircraft starts its day, is the swing factor no table can capture; it is why identical trips quote 30% apart. Recompute this route with your own passenger count, or check a quote you already have.
RATE BASIS Private Jet Card Comparisons: Q2 2026 jet card rate report privatejetcardcomparisons.com read 2026-08-31 · NATA: 2026 federal excise tax rates (IRS Revenue Procedure 2025-32) nata.aero read 2026-08-31
Class rate ranges are cross-checked each quarter against five published seller rate cards, printed side by side in the cost index.
When you fly matters
Weather, not season, is the variable: winter deicing events at both ends can add $3,000 to $10,000 per stop, and summer convective lines cause more delays than snow does.
The empty-leg angle
Empty legs exist on this route but supply is thin; treat any listing as a bonus, not a strategy. How empty legs work.
Aircraft that fit this mission
- Pilatus PC-12 NGX: The Swiss workhorse: single-engine economics, big cross-section, happy on gravel strips.
- Embraer Phenom 100EV: Airline-grade avionics in the smallest Embraer; brisk for the class.
- Embraer Phenom 300E: Best-selling light jet for over a decade, and the default answer under 2,000 nm.
Prices apply in reverse (MDW → TEB), though empty-leg supply and peak days often differ by direction. Ready for quotes? Build a proper RFP and make brokers respond to your brief.