Charter Chicago to San Juan privately from US$59,500, about 4h 14m gate to gate. Request your price in minutes.
Private jet charter from Chicago (ORD) to San Juan (SJU), and from San Juan (SJU) back to Chicago (ORD).
Chicago and San Juan lie approximately 3,338 km apart (2,074 mi / 1,802 nm) on a direct routing.
From US$59,500 · Reply within the hour · No obligation
Expect US$59,500 – US$154,000 for a one-way charter between Chicago and San Juan, depending on the aircraft — a super midsize jet sits at the lower end, larger jets above. Pets are welcome in-cabin on every option.
Intercontinental comfort with a full stand-up cabin and separate sleeping area. 9-12 seats and 5,926 km of range make it a dependable fit here.
Large-group luxury with full galley, lie-flat beds, and dedicated crew rest. 12-16 seats and 7,400 km of range make it a dependable fit here.
| Category | Outbound | Return (±10% wind) | From (USD) | Seats |
|---|---|---|---|---|
| Super Midsize Jet · rec. | 4h 14m | 3h 49m – 4h 39m | US$81,000 | 9-12 |
| Heavy Jet | 4h 14m | 3h 49m – 4h 39m | US$110,000 | 12-16 |
| Aircraft | Flight time | Cost range (USD) | Passengers |
|---|---|---|---|
| Challenger 350 | 4h 14m | US$81,000 – US$100,000 | 9-12 |
| Cessna Citation Longitude | 4h 14m | US$89,000 – US$100,000 | 9-12 |
| Embraer Praetor 600 | 4h 20m | US$97,000 – US$100,000 | 9-12 |
| Aircraft | Flight time | Cost range (USD) | Passengers |
|---|---|---|---|
| Challenger 605 | 4h 14m | US$110,000 – US$154,000 | 12-16 |
| Falcon 2000LXS | 4h 07m | US$121,000 – US$169,500 | 10-14 |
| Gulfstream G450 | 4h 07m | US$132,000 – US$185,000 | 13-16 |
The return leg uses the same aircraft and guide pricing; timings may shift up to ±10% depending on winds.
Guide prices are one-way estimates incl. positioning; taxes/handling extra. Round-trip and one-way both available.
On Chicago–San Juan, pricing is a function of the route distance and headwinds, fuel costs across the regions you cross, and handling charges at origin and destination. We verify against current aircraft availability before quoting a firm price. International routing adds overflight permits and customs clearance to the final figure.
Both cities are served by several airports, giving flexibility on slots and routing:
Chicago, United States: Chicago O'Hare International Airport, Dupage Airport, Chicago Executive Airport, Chicago Midway International Airport, Gary/Chicago International Airport and Lewis University Airport.
San Juan, Puerto Rico: Luis Munoz Marin International Airport, Fernando Luis Ribas Dominicci Airport and José Aponte de la Torre Airport.
| Chicago O'Hare International Airport | Luis Munoz Marin International Airport | |
|---|---|---|
| Code | KORD / ORD | TJSJ / SJU |
| Longest hard runway | 13,000 ft | 10,002 ft |
| Surface | Concrete | Asphalt |
| Field elevation | 680 ft | 9 ft |
| Aircraft | Runway | Range | On this route |
|---|---|---|---|
| Embraer Phenom 100EV Very Light Jet |
3,200 ft 6,802 ft spare |
2,180 km 1,993 km short after reserves |
Fuel stop needed |
| Cessna Citation M2 Very Light Jet |
2,900 ft 7,102 ft spare |
2,410 km 1,763 km short after reserves |
Fuel stop needed |
| Cessna Citation CJ3+ Light Jet |
3,500 ft 6,502 ft spare |
3,700 km 473 km short after reserves |
Fuel stop needed |
| Embraer Phenom 300E Light Jet |
3,278 ft 6,724 ft spare |
3,650 km 523 km short after reserves |
Fuel stop needed |
| Cessna Citation XLS+ Midsize Jet |
4,200 ft 5,802 ft spare |
3,900 km 273 km short after reserves |
Fuel stop needed |
| Hawker 900XP Midsize Jet |
5,576 ft 4,426 ft spare |
4,600 km 427 km spare after reserves |
Non-stop |
| Challenger 350 Super Midsize Jet |
4,930 ft 5,072 ft spare |
5,926 km 1,753 km spare after reserves |
Non-stop |
| Cessna Citation Longitude Super Midsize Jet |
4,900 ft 5,102 ft spare |
6,400 km 2,227 km spare after reserves |
Non-stop |
| Embraer Praetor 600 Super Midsize Jet |
4,692 ft 5,310 ft spare |
7,220 km 3,047 km spare after reserves |
Non-stop |
| Challenger 605 Heavy Jet |
5,440 ft 4,562 ft spare |
7,400 km 3,227 km spare after reserves |
Non-stop |
| Gulfstream G450 Heavy Jet |
5,300 ft 4,702 ft spare |
7,800 km 3,627 km spare after reserves |
Non-stop |
| Falcon 2000LXS Heavy Jet |
4,790 ft 5,212 ft spare |
7,400 km 3,227 km spare after reserves |
Non-stop |
| Bombardier Global 7500 Ultra Long Range Jet |
6,000 ft 4,002 ft spare |
14,260 km 10,087 km spare after reserves |
Non-stop |
| Bombardier Global 6000 Long Range Jet |
5,800 ft 4,202 ft spare |
11,112 km 6,939 km spare after reserves |
Non-stop |
| Gulfstream G650 Long Range Jet |
6,000 ft 4,002 ft spare |
12,960 km 8,787 km spare after reserves |
Non-stop |
| Falcon 8X Long Range Jet |
4,800 ft 5,202 ft spare |
11,945 km 7,772 km spare after reserves |
Non-stop |
Alternates within range: Dupage Airport (7,571 ft, 30 km) · Chicago Executive Airport (5,001 ft, 15 km) · Chicago Midway International Airport (6,522 ft, 25 km) · Gary/Chicago International Airport (8,859 ft, 57 km) · Fernando Luis Ribas Dominicci Airport (5,317 ft, 10 km) · José Aponte de la Torre Airport (11,000 ft, 44 km) · Antonio Rivera Rodriguez Airport (4,301 ft, 63 km) · Santa Isabel Airport (4,000 ft, 67 km)
One of private aviation's quiet advantages: your pet sits with you throughout. No cargo, no separation.
Charter safety is non-negotiable. All operators on our network carry current AOC certification and third-party audits.
Send your request and expect a real answer within the hour — not an automated holding reply, but live options with pricing.
You set the departure time. The aircraft waits for you, not the other way around.
The Chicago to San Juan route is a popular international private-jet path for both business travellers and leisure flyers seeking direct access without commercial schedules.
Budget US$59,500 – US$154,000 one-way depending on aircraft; a super midsize jet sits at the entry point. We confirm a firm figure against live availability.
Roughly 4h 14m gate to gate across the 3,338 km sector — timings shift a little with winds and aircraft.
This sector is mainly served by Super Midsize Jet, Heavy Jet. We lead with a super midsize jet for the best balance of cost, cabin and range.
Often yes: same-day and next-day Chicago–San Juan departures are possible when aircraft and crew are positioned nearby.
Absolutely — pets travel in the cabin with you on this route; just tell us the details when you ask for a quote.
Of course: San Juan to Chicago runs on the same aircraft and pricing, so round trips are straightforward.
Other flights from Chicago | San Juan | United States | North America
