Drake Flies from Hamilton to Toronto the Week of OVO Fest Planning

Drake flew from Hamilton’s John C. Munro airport to Toronto Pearson on June 4, a 22-minute hop aboard the Boeing 767-200ER N767CJ. The short northward leg comes midway through a cluster of regional trips — including recent flights to Montreal and back — and places the rapper in his adopted hometown.

The same week, per Billboard and multiple venue listings, Drake’s OVO team is finalizing details for the annual OVO Fest, usually held in Toronto in late summer, as well as preliminary routing for his Summer Sixteen tour. Sources at Live Nation have confirmed that the label is in active booking mode for stadium dates that begin in the fall, with Pearson serving as the operational hub for those meetings.

This flight matches a pattern from his briefing: regular shuttles between CYHM and CYYZ for label business, tour rehearsals, and OVO corporate work. At under 60 nautical miles, the flight is as much a privacy choice as a convenience — the 767 avoids Pearson’s commercial traffic and keeps the OVO camp out of the general terminal scrum.