Private charter between Windsor Locks and Chicago starts at US$20,000 aboard a light jet.
Private jet charter from Windsor Locks (BDL) to Chicago (ORD), and from Chicago (ORD) back to Windsor Locks (BDL).
As the crow flies, Windsor Locks to Chicago is roughly 1,257 kilometres — 781 miles, or 679 nautical miles.
From US$20,000 · Reply within the hour · No obligation
Guide pricing for Windsor Locks–Chicago spans US$20,000 – US$54,500: from a light jet (Cessna Citation CJ3+) at the entry level to a super midsize jet (Challenger 350) at the top. All cabins are pet-friendly — travel with dogs and pets beside you.
The popular choice for this distance — strong value and cabin comfort. It seats 6-8 and is a frequent choice on sectors of this length.
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.
| Category | Outbound | Return (±10% wind) | From (USD) | Seats |
|---|---|---|---|---|
| Light Jet · rec. | 2h 01m | 1h 49m – 2h 13m | US$20,000 | 6-8 |
| Midsize Jet | 1h 58m | 1h 46m – 2h 10m | US$28,500 | 7-9 |
| Super Midsize Jet | 1h 51m | 1h 40m – 2h 02m | US$39,000 | 9-12 |
| Aircraft | Flight time | Cost range (USD) | Passengers |
|---|---|---|---|
| Cessna Citation CJ3+ | 2h 01m | US$20,000 – US$28,000 | 6-8 |
| Embraer Phenom 300E | 1h 57m | US$22,000 – US$31,000 | 6-8 |
| Learjet 75 Liberty | 1h 52m | US$24,000 – US$33,500 | 6-8 |
| Aircraft | Flight time | Cost range (USD) | Passengers |
|---|---|---|---|
| Cessna Citation XLS+ | 1h 58m | US$28,500 – US$40,000 | 7-9 |
| Hawker 900XP | 1h 57m | US$31,500 – US$44,000 | 7-9 |
| Embraer Praetor 500 | 1h 53m | US$34,000 – US$48,000 | 8-10 |
| Aircraft | Flight time | Cost range (USD) | Passengers |
|---|---|---|---|
| Challenger 350 | 1h 51m | US$39,000 – US$54,500 | 9-12 |
| Cessna Citation Longitude | 1h 51m | US$43,000 – US$60,000 | 9-12 |
| Embraer Praetor 600 | 1h 53m | US$47,000 – US$65,500 | 9-12 |
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.
Several variables shape what you pay for a Windsor Locks–Chicago charter: the distance and prevailing winds on the day, fuel costs at both ends, handling and landing fees at both airports, and the specific aircraft confirmed against live availability.
Private departures on this route use the following airports — we will recommend the best fit for your schedule:
Windsor Locks, United States: Bradley International Airport, Hartford Brainard Airport, Kenley Airport, Striplin Airfield, Thomsen Field and Oakleaf 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. 6-8 passengers, one aircraft, complete privacy.
Private jets are pet-friendly by default. Your companion flies in the cabin with you, not in cargo.
Charter safety is non-negotiable. All operators on our network carry current AOC certification and third-party audits.
Our team responds to Windsor Locks–Chicago quote requests within the hour during business hours, with real aircraft options.
The Windsor Locks to Chicago route is a popular domestic private-jet path for both business travellers and leisure flyers seeking direct access without commercial schedules.
As a guide, charter ranges US$20,000 – US$54,500 one-way — from a light jet (Cessna Citation CJ3+) at the lower end. Final pricing depends on dates, group size and availability.
About 2h 01m in the air over 1,257 km (781 miles), similar both ways; larger jets are marginally faster.
Light Jet, Midsize Jet, Super Midsize Jet are the usual choices here; our pick is a light jet for value and comfort on this distance.
Yes — we handle last-minute Windsor Locks–Chicago charters, often with as little as 4 hours' notice, subject to aircraft and crew availability.
Yes. Our Windsor Locks–Chicago charters are dog- and pet-friendly with in-cabin access — note your pet in the enquiry.
Of course: Chicago to Windsor Locks runs on the same aircraft and pricing, so round trips are straightforward.
Other flights from Windsor Locks | Chicago | United States | North America
