
Chicago → Grand Cayman
A private flight from Chicago to Grand Cayman covers 1,390 nautical miles (2,574 km) and takes about 3h 37m in a light jet. For 4 passengers, expect roughly $23,781 – $34,636 one-way — about $7,302 per seat.
Price by aircraft class · 4 passengers
| Aircraft class | Non-stop? | Flight time | One-way | Round trip, same day | Round trip, 2–3 days | Per seat (one-way) | CO₂ / pax |
|---|---|---|---|---|---|---|---|
| Turboprop King Air 360, PC-12 · up to 8 seats | 1 fuel stop | 6h 01m | $24,416 – $36,035 | $38,394 – $50,820 | $44,194 – $63,420 | $7,556 | 863 kg |
| Very light jet Phenom 100, Vision Jet, HondaJet · up to 5 seats | 1 fuel stop | 4h 48m | $22,825 – $32,486 | $36,038 – $46,050 | $42,238 – $59,450 | $6,914 | 920 kg |
| Light jet Phenom 300E, CJ4, PC-24 · up to 7 seats | Non-stop | 3h 37m | $23,781 – $34,636 | $37,279 – $48,705 | $44,779 – $65,705 | $7,302 | 1,295 kg |
| Midsize jet Citation XLS, Praetor 500, Learjet 75 · up to 8 seats | Non-stop | 3h 28m | $30,535 – $44,437 | $47,901 – $62,534 | $56,901 – $83,534 | $9,372 | 1,903 kg |
| Super-midsize jet Challenger 3500, Praetor 600, Longitude · up to 9 seats | Non-stop | 3h 19m | $36,830 – $53,555 | $57,816 – $75,421 | $68,316 – $100K | $11,298 | 2,225 kg |
| Large jet Challenger 650, Falcon 2000, G450 · up to 12 seats | Non-stop | 3h 15m | $46,191 – $71,166 | $72,679 – $100K | $85,179 – $132K | $14,670 | 2,727 kg |
| Ultra-long-range jet G650ER, Global 7500, Falcon 8X · up to 14 seats | Non-stop | 3h 08m | $56,543 – $86,735 | $89,066 – $122K | $104K – $161K | $17,910 | 3,601 kg |
| VIP airliner BBJ, ACJ320neo · up to 19 seats | Non-stop | 3h 19m | $91,393 – $162K | $145K – $229K | $166K – $294K | $31,695 | 7,151 kg |
Editorial estimates from 2026 benchmark hourly rates; greyed classes are too small for your party. One-way prices include a share of the empty return leg; “2–3 days” adds crew overnights and daily minimums. Peak dates run 20–40% higher; empty legs can be 50–75% lower. How charter pricing works →
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Aircraft that fly Chicago–Grand Cayman non-stop
Chicago: where you’d land
- Chicago Executive Airport KPWK
Business-aviation airport · 5,001 ft runway · 45 min to centre · customs · 24h - Chicago Midway International Airport KMDW
Airport with private terminal · 6,522 ft runway · 25 min to centre · customs · 24h - Chicago O'Hare International Airport KORD
Major hub · 13,000 ft runway · 40 min to centre · customs · 24h
Grand Cayman: where you’d land
- Owen Roberts International Airport MWCR
Airport with private terminal · 6,596 ft runway · 10 min to centre · customs
Private vs airline vs first class on this route
| Door to door | CO₂ / passenger | Price per seat | |
|---|---|---|---|
| Private (light jet) | 4.6 h | 1,295 kg | $7,302 |
| Airline, economy | 6.9 h | 257 kg | Typically $309–$772 |
| Airline, first / business | 6.4 h | 1029 kg | Typically $1,287–$3,088 |
Door-to-door assumes 15 minutes at the private terminal vs 2.5 hours for airline check-in and security. Airline fares are indicative ranges by distance, not live prices.


