Private charter between Chicago and Winnipeg starts at US$12,500 aboard a midsize jet.
We fly Chicago (ORD) ⇄ Winnipeg (YWG) in both directions, on the same aircraft and guide pricing.
The straight-line distance between Chicago and Winnipeg is about 1,138 km (707 miles), or 614 nautical miles.
From US$12,500 · Reply within the hour · No obligation
Chartering a private jet from Chicago to Winnipeg (and Winnipeg to Chicago) ranges from US$12,500 for a midsize jet like the Cessna Citation XLS+, up to US$37,000 for a midsize jet such as the Cessna Citation XLS+. 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. 7-9 seats and 3,900 km of range make it a dependable fit here.
| Category | Outbound | Return (±10% wind) | From (USD) | Seats |
|---|---|---|---|---|
| Midsize Jet · rec. | 1h 49m | 1h 38m – 2h 00m | US$26,500 | 7-9 |
| Aircraft | Flight time | Cost range (USD) | Passengers |
|---|---|---|---|
| Cessna Citation XLS+ | 1h 49m | US$26,500 – US$37,000 | 7-9 |
| Hawker 900XP | 1h 48m | US$29,000 – US$40,500 | 7-9 |
| Embraer Praetor 500 | 1h 44m | US$32,000 – US$44,500 | 8-10 |
Same aircraft, same route — return pricing is symmetric; flight times can vary about ±10% with wind direction.
Guide prices are one-way estimates incl. positioning; taxes/handling extra. Round-trip and one-way both available.
Every Chicago–Winnipeg 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.
You can fly to or from any of these airports at each end; we match the most convenient to your trip:
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.
Winnipeg, Canada: Winnipeg / James Armstrong Richardson International Airport.
| Chicago O'Hare International Airport | Winnipeg / James Armstrong Richardson International Airport | |
|---|---|---|
| Code | KORD / ORD | CYWG / YWG |
| Longest hard runway | 13,000 ft | 11,000 ft |
| Surface | Concrete | Asphalt |
| Field elevation | 680 ft | 783 ft |
| Aircraft | Needs | Range | On this route |
|---|---|---|---|
| Pilatus PC-12 NGX Turboprop |
1,500 ft | 1,800 km | Non-stop |
| King Air 350 Turboprop |
2,000 ft | 2,700 km | Non-stop |
| Embraer Phenom 100EV Very Light Jet |
3,200 ft | 2,180 km | Non-stop |
| Cessna Citation M2 Very Light Jet |
2,900 ft | 2,410 km | Non-stop |
| King Air 250 Turboprop |
3,000 ft | 2,900 km | Non-stop |
| 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) · Winnipeg / Lyncrest Airport · Winnipeg / St. Andrews Airport (3,000 ft, 22 km) · St. François Xavier Airport · Starbuck Airport
We publish the price band (US$12,500 – US$37,000) so you can plan before committing. The confirmed quote has no surprises.
The cabin is your own from departure to landing — work, rest or hold sensitive conversations without concern.
Travel Chicago–Winnipeg with your dog, cat or other pet beside you in the cabin. Simply flag it when you request a quote.
We do the due diligence on every operator so you don't have to. Certified, insured, and audited before your wheels leave the ground.
The Chicago to Winnipeg route is a popular international private-jet path for both business travellers and leisure flyers seeking direct access without commercial schedules.
Budget US$12,500 – US$37,000 one-way depending on aircraft; a midsize jet sits at the entry point. We confirm a firm figure against live availability.
About 1h 49m in the air over 1,138 km (707 miles), similar both ways; larger jets are marginally faster.
Midsize Jet are the usual choices here; our pick is a midsize jet for value and comfort on this distance.
Often yes: same-day and next-day Chicago–Winnipeg departures are possible when aircraft and crew are positioned nearby.
Yes. Our Chicago–Winnipeg charters are dog- and pet-friendly with in-cabin access — note your pet in the enquiry.
Of course: Winnipeg to Chicago runs on the same aircraft and pricing, so round trips are straightforward.
Other flights from Chicago | Winnipeg | United States | North America
