Fly private between Chicago and San Jose Del Cabo from US$53,500 for a midsize jet (Cessna Citation XLS+). Get an instant, guaranteed quote.
Private jet charter from Chicago (ORD) to San Jose Del Cabo (SJD), and from San Jose Del Cabo (SJD) back to Chicago (ORD).
As the crow flies, Chicago to San Jose Del Cabo is roughly 2,909 kilometres — 1,808 miles, or 1,571 nautical miles.
From US$53,500 · Reply within the hour · No obligation
Expect US$53,500 – US$139,500 for a one-way charter between Chicago and San Jose Del Cabo, depending on the aircraft — a midsize jet sits at the lower end, larger jets above. Pets are welcome in-cabin on every option.
A stand-up cabin and more baggage room for medium-haul comfort. With seating for 7-9, it balances cabin comfort against running cost.
Intercontinental comfort with a full stand-up cabin and separate sleeping area. With seating for 9-12, it balances cabin comfort against running cost.
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 |
|---|---|---|---|---|
| Midsize Jet · rec. | 4h 02m | 3h 38m – 4h 26m | US$53,500 | 7-9 |
| Super Midsize Jet | 3h 45m | 3h 23m – 4h 08m | US$73,000 | 9-12 |
| Heavy Jet | 3h 45m | 3h 23m – 4h 08m | US$99,500 | 12-16 |
| Aircraft | Flight time | Cost range (USD) | Passengers |
|---|---|---|---|
| Cessna Citation XLS+ | 4h 02m | US$53,500 – US$70,000 | 7-9 |
| Hawker 900XP | 3h 59m | US$59,000 – US$70,000 | 7-9 |
| Embraer Praetor 500 | 3h 49m | US$64,000 – US$70,000 | 8-10 |
| Aircraft | Flight time | Cost range (USD) | Passengers |
|---|---|---|---|
| Challenger 350 | 3h 45m | US$73,000 – US$100,000 | 9-12 |
| Cessna Citation Longitude | 3h 45m | US$80,500 – US$100,000 | 9-12 |
| Embraer Praetor 600 | 3h 49m | US$87,500 – US$100,000 | 9-12 |
| Aircraft | Flight time | Cost range (USD) | Passengers |
|---|---|---|---|
| Challenger 605 | 3h 45m | US$99,500 – US$139,500 | 12-16 |
| Falcon 2000LXS | 3h 38m | US$109,500 – US$153,500 | 10-14 |
| Gulfstream G450 | 3h 38m | US$119,500 – US$167,500 | 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.
Every Chicago–San Jose Del Cabo quote is built fresh: distance and wind factor, fuel costs across the regions you cross, landing and handling fees, and live aircraft positioning. No estimates — the number we give you is the number you pay. 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, Chicago Midway International Airport and Lansing Municipal Airport.
San Jose Del Cabo, Mexico: Los Cabos International Airport and Los Frailes Airstrip.
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.
You speak to people, not chatbots. A response with real aircraft options is typically with you within the hour.
You set the departure time. The aircraft waits for you, not the other way around.
Demand on Chicago–San Jose Del Cabo comes from corporate trips and getaways in equal measure — a international route where private charter pays off in time and privacy.
As a guide, charter ranges US$53,500 – US$139,500 one-way — from a midsize jet (Cessna Citation XLS+) at the lower end. Final pricing depends on dates, group size and availability.
About 4h 02m in the air over 2,909 km (1,808 miles), similar both ways; larger jets are marginally faster.
Midsize Jet, Super Midsize Jet, Heavy Jet are the usual choices here; our pick is a midsize jet for value and comfort on this distance.
Yes — we handle last-minute Chicago–San Jose Del Cabo charters, often with as little as 4 hours' notice, subject to aircraft and crew availability.
Yes. Our Chicago–San Jose Del Cabo charters are dog- and pet-friendly with in-cabin access — note your pet in the enquiry.
Of course: San Jose Del Cabo to Chicago runs on the same aircraft and pricing, so round trips are straightforward.
Other flights from Chicago | San Jose Del Cabo | United States | North America
