
Chicago → San Juan
A private flight from Chicago to San Juan covers 1,789 nautical miles (3,314 km) and takes about 4h 22m in a midsize jet. For 4 passengers, expect roughly $37,620 – $54,973 one-way — about $11,574 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 | 7h 26m | $29,611 – $43,899 | $46,387 – $61,668 | $52,187 – $74,268 | $9,189 | 1,068 kg |
| Very light jet Phenom 100, Vision Jet, HondaJet · up to 5 seats | 1 fuel stop | 5h 53m | $27,318 – $39,064 | $42,951 – $55,123 | $49,151 – $68,523 | $8,298 | 1,127 kg |
| Light jet Phenom 300E, CJ4, PC-24 · up to 7 seats | 1 fuel stop | 5h 19m | $35,235 – $50,940 | $55,593 – $72,124 | $63,093 – $89,124 | $10,772 | 1,906 kg |
| Midsize jet Citation XLS, Praetor 500, Learjet 75 · up to 8 seats | Non-stop | 4h 22m | $37,620 – $54,973 | $58,800 – $77,067 | $67,800 – $98,067 | $11,574 | 2,403 kg |
| Super-midsize jet Challenger 3500, Praetor 600, Longitude · up to 9 seats | Non-stop | 4h 11m | $45,301 – $66,153 | $70,848 – $92,797 | $81,348 – $118K | $13,932 | 2,807 kg |
| Large jet Challenger 650, Falcon 2000, G450 · up to 12 seats | Non-stop | 4h 06m | $56,693 – $87,811 | $88,835 – $123K | $101K – $155K | $18,063 | 3,439 kg |
| Ultra-long-range jet G650ER, Global 7500, Falcon 8X · up to 14 seats | Non-stop | 3h 57m | $69,267 – $107K | $109K – $150K | $124K – $189K | $22,013 | 4,538 kg |
| VIP airliner BBJ, ACJ320neo · up to 19 seats | Non-stop | 4h 11m | $112K – $200K | $176K – $281K | $197K – $346K | $38,960 | 9,022 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–San Juan 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
San Juan: where you’d land
- Fernando Luis Ribas Dominicci Airport (Isla Grande) TJIG
Business-aviation airport · 5,544 ft runway · 10 min to centre · customs - Luis Muñoz Marín International Airport TJSJ
Major hub · 10,400 ft runway · 20 min to centre · customs · 24h
Private vs airline vs first class on this route
| Door to door | CO₂ / passenger | Price per seat | |
|---|---|---|---|
| Private (midsize jet) | 5.4 h | 2,403 kg | $11,574 |
| Airline, economy | 7.7 h | 331 kg | Typically $398–$994 |
| Airline, first / business | 7.2 h | 1326 kg | Typically $1,657–$3,977 |
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.



