Fly private between Chicago and San Jose Del Cabo from US$53,500 for a midsize jet (Cessna Citation XLS+). Get an instant 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.
| 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 |
| 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 |
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. The figure shown is a guide; we confirm a firm price against live availability. 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 Jose Del Cabo, Mexico: Los Cabos International Airport and Cabo San Lucas International Airport.
| Chicago O'Hare International Airport | Los Cabos International Airport | |
|---|---|---|
| Code | KORD / ORD | MMSD / SJD |
| Longest hard runway | 13,000 ft | 9,843 ft |
| Surface | Concrete | Asphalt |
| Field elevation | 680 ft | 374 ft |
| Aircraft | Needs | Range | On this route |
|---|---|---|---|
| Embraer Phenom 100EV Very Light Jet |
3,200 ft | 2,180 km | Fuel stop needed |
| Cessna Citation M2 Very Light Jet |
2,900 ft | 2,410 km | Fuel stop needed |
| Cessna Citation CJ3+ Light Jet |
3,500 ft | 3,700 km | Non-stop |
| Embraer Phenom 300E Light Jet |
3,278 ft | 3,650 km | Non-stop |
| Cessna Citation XLS+ Midsize Jet |
4,200 ft | 3,900 km | Non-stop |
| Hawker 900XP Midsize Jet |
5,576 ft | 4,600 km | Non-stop |
| Challenger 350 Super Midsize Jet |
4,930 ft | 5,926 km | Non-stop |
| Cessna Citation Longitude Super Midsize Jet |
4,900 ft | 6,400 km | Non-stop |
| Embraer Praetor 600 Super Midsize Jet |
4,692 ft | 7,220 km | Non-stop |
| Challenger 605 Heavy Jet |
5,440 ft | 7,400 km | Non-stop |
| Gulfstream G450 Heavy Jet |
5,300 ft | 7,800 km | Non-stop |
| Falcon 2000LXS Heavy Jet |
4,790 ft | 7,400 km | Non-stop |
| Bombardier Global 7500 Ultra Long Range Jet |
6,000 ft | 14,260 km | Non-stop |
| Bombardier Global 6000 Long Range Jet |
5,800 ft | 11,112 km | Non-stop |
| Gulfstream G650 Long Range Jet |
6,000 ft | 12,960 km | Non-stop |
| Falcon 8X Long Range Jet |
4,800 ft | 11,945 km | 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) · Cabo San Lucas International Airport (6,998 ft, 32 km) · Cabo Real Heliport · Destiladeras Cabo Este Heliport · Cabo Sky Tours Heliport
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 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
