Fly private between Montego Bay and Chicago from US$51,500 for a midsize jet (Cessna Citation XLS+). Get an instant, guaranteed quote.
We fly Montego Bay (MBJ) ⇄ Chicago (ORD) in both directions, on the same aircraft and guide pricing.
Montego Bay and Chicago lie approximately 2,776 km apart (1,725 mi / 1,499 nm) on a direct routing.
From US$51,500 · Reply within the hour · No obligation
Chartering a private jet from Montego Bay to Chicago (and Chicago to Montego Bay) ranges from US$51,500 for a midsize jet like the Cessna Citation XLS+, up to US$134,500 for a heavy jet such as the Challenger 605. Charters on this route are dog- and pet-friendly, with in-cabin access for your companion.
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. It seats 9-12 and is a frequent choice on sectors of this length.
Large-group luxury with full galley, lie-flat beds, and dedicated crew rest. It seats 12-16 and is a frequent choice on sectors of this length.
| Category | Outbound | Return (±10% wind) | From (USD) | Seats |
|---|---|---|---|---|
| Midsize Jet · rec. | 3h 52m | 3h 29m – 4h 15m | US$51,500 | 7-9 |
| Super Midsize Jet | 3h 35m | 3h 14m – 3h 57m | US$70,500 | 9-12 |
| Heavy Jet | 3h 35m | 3h 14m – 3h 57m | US$96,000 | 12-16 |
| Aircraft | Flight time | Cost range (USD) | Passengers |
|---|---|---|---|
| Cessna Citation XLS+ | 3h 52m | US$51,500 – US$70,000 | 7-9 |
| Hawker 900XP | 3h 50m | US$56,500 – US$70,000 | 7-9 |
| Embraer Praetor 500 | 3h 40m | US$62,000 – US$70,000 | 8-10 |
| Aircraft | Flight time | Cost range (USD) | Passengers |
|---|---|---|---|
| Challenger 350 | 3h 35m | US$70,500 – US$98,500 | 9-12 |
| Cessna Citation Longitude | 3h 35m | US$77,500 – US$100,000 | 9-12 |
| Embraer Praetor 600 | 3h 40m | US$84,500 – US$100,000 | 9-12 |
| Aircraft | Flight time | Cost range (USD) | Passengers |
|---|---|---|---|
| Challenger 605 | 3h 35m | US$96,000 – US$134,500 | 12-16 |
| Falcon 2000LXS | 3h 29m | US$105,500 – US$148,000 | 10-14 |
| Gulfstream G450 | 3h 29m | US$115,000 – US$161,500 | 13-16 |
Outbound and return are priced alike on identical aircraft; expect roughly ±10% variation in time by wind.
Guide prices are one-way estimates incl. positioning; taxes/handling extra. Round-trip and one-way both available.
On Montego Bay–Chicago, 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.
You can fly to or from any of these airports at each end; we match the most convenient to your trip:
Montego Bay, Jamaica: Sangster International Airport.
Chicago, United States: Chicago O'Hare International Airport, Chicago Midway International Airport and Lansing Municipal Airport.
No shared cabin, no middle seats, no compromise. 7-9 passengers, one aircraft, complete privacy.
One of private aviation's quiet advantages: your pet sits with you throughout. No cargo, no separation.
We work exclusively with operators who hold the correct certifications and maintenance records for the routes they fly.
You speak to people, not chatbots. A response with real aircraft options is typically with you within the hour.
Montego Bay–Chicago is a frequently chartered international sector for executives and families alike, prized for flexibility and time saved.
Budget US$51,500 – US$134,500 one-way depending on aircraft; a midsize jet sits at the entry point. We confirm a firm figure against live availability.
About 3h 52m in the air over 2,776 km (1,725 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 Montego Bay–Chicago charters, often with as little as 4 hours' notice, subject to aircraft and crew availability.
Absolutely — pets travel in the cabin with you on this route; just tell us the details when you ask for a quote.
Of course: Chicago to Montego Bay runs on the same aircraft and pricing, so round trips are straightforward.
Other flights from Montego Bay | Chicago | Jamaica | North America
