Chicago → Toronto
Fly Private from Chicago to Toronto
Take advantage of fast, cross-border travel between two global cities. Triumph Jets offers private jet flights from Chicago to Toronto for business professionals, families, and entertainers. Depart from Midway or Chicago Executive and land seamlessly at Pearson or Billy Bishop airports.
Efficient, stylish, and stress-free, this route is ideal for those traveling frequently between the U.S. and Canada.
Estimated Pricing by Aircraft Class
Private charter pricing for this route varies by aircraft size and availability. Contact us for current quotes and availability.
Visiting Toronto, Ontario, Canada
Charter This Route
Get a personalized quote for your private flight from Chicago to Toronto. Our team will find the perfect aircraft for your needs and budget.
Frequently Asked Questions
Please refer to the Estimated Pricing by Aircraft Class section above for the displayed estimates. Final pricing depends on your itinerary, aircraft availability, and operating requirements. Contact Triumph Jets for a personalized quote.
Downtown Toronto, Mississauga, Oakville, Vaughan, Markham, Scarborough, North York, and nearby areas.
- The St. Regis Toronto
- Four Seasons Hotel Toronto
- The Ritz-Carlton, Toronto
- 1 Hotel Toronto
- Shangri-La Toronto
- Visit the CN Tower
- Explore the Distillery District
- Enjoy shopping in Yorkville
- Attend events at Scotiabank Arena
- Take in the views from Toronto Islands