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A Chicago River tour boat passes in front of Trump Tower

Private Jet from Naples to Chicago

The winter route between Chicago and Naples, one of Florida’s most popular Midwest snowbird towns.

Estimate this trip

Naples to Chicago by Jet Size

APF to PWK is 1,157 statute miles (1,005 nautical). Showing aircraft that fly it nonstop (turboprops, very light jets would need a fuel stop). Estimates exclude taxes, fees and repositioning.

Jet sizeSeatsTimeOne way, estimated
Light jet5–72 hr 55 min$12,800–$18,500
Midsize jet7–92 hr 50 mindaily minimum$16,600–$21,500
Super-midsize jet8–102 hr 40 mindaily minimum$20,500–$31,000
Heavy jet10–162 hr 40 mindaily minimum$36,500–$56,000
Ultra-long-range jet12–192 hr 35 mindaily minimum$49,500–$86,500

Tips for This Route

Naples Noise Rules

Naples Airport enforces strict noise rules, so older, louder jets cannot use it. The operators we use fly compliant aircraft.

Season Peaks

Most travel runs from after Thanksgiving to Easter. Spring flights north are busy, so book your return early.

Departure and Arrival Airports

Other options: Southwest Florida International (RSW) or Marco Island (MKY) instead of Naples; Midway (MDW) or DuPage (DPA) instead of Chicago Executive.

Aircraft for Naples to Chicago

Listed with the aircraft that fly this trip nonstop first.

Cessna Citation CJ3 light jet parked on the ramp
Light jet

Cessna Citation CJ3

Seats
6–7
Range
2,040 nm
Per hour
$3.8k+
Cessna Citation XLS/XLS+
Midsize jet

Cessna Citation XLS/XLS+

Seats
7–9
Range
2,100 nm
Per hour
$4.8k+
Bombardier Challenger 300/350
Super-midsize jet

Bombardier Challenger 300/350

Seats
8–10
Range
3,200 nm
Per hour
$6.0k+

Naples to Chicago Questions

How long is a private flight from Naples to Chicago?

About 2 hr 55 min in a light jet and about 2 hr 35 min in an ultra-long-range jet, from takeoff to landing.

How much does a private jet from Naples to Chicago cost?

Estimates start at about $12,800 to $18,500 one way in a light jet, before taxes, fees and repositioning. Larger jets cost more; see the table above for every size. Your quote shows the exact price for your dates.

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