Private charter between Windsor Locks and Chicago starts at US$20,000 aboard a midsize 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 midsize jet (Cessna Citation XLS+) 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.
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 |
|---|---|---|---|---|
| Midsize Jet · rec. | 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 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, Westfield-Barnes Regional Airport, Westover Metropolitan Airport / Westover Air Reserve Base and Waterbury Oxford Airport.
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.
| Bradley International Airport | Chicago O'Hare International Airport | |
|---|---|---|
| Code | KBDL / BDL | KORD / ORD |
| Longest hard runway | 9,510 ft | 13,000 ft |
| Surface | Asphalt | Concrete |
| Field elevation | 173 ft | 680 ft |
All 16 aircraft we quote for Windsor Locks to Chicago can use both airfields and fly the route non-stop. Bradley International Airport has 9,510 ft and Chicago O'Hare International Airport 13,000 ft, both comfortably beyond the 6,000 ft the largest types here need, so field length is not what decides the aircraft on this route — cabin size and range are. The leg is 1,257 km.
Alternates within range: Westfield-Barnes Regional Airport (9,000 ft, 24 km) · Westover Metropolitan Airport / Westover Air Reserve Base (11,597 ft, 31 km) · Waterbury Oxford Airport (5,800 ft, 63 km) · Hartford Brainard Airport (4,417 ft, 23 km) · 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)
No shared cabin, no middle seats, no compromise. 7-9 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 midsize jet (Cessna Citation XLS+) at the lower end. Final pricing depends on dates, group size and availability.
About 1h 58m gate to gate over 1,257 km (781 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 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
