How long is the train ride?

The journey from Winnipeg to Oshawa takes about 37 hours with transfers.

Is there a direct flight from Brandon?

No, you must fly from Winnipeg (YWG).

What is the best way to travel?

Flying is the most efficient method.

Do I need a car in Oshawa?

A car is helpful for exploring the region, but not strictly necessary in the city.

It is comparable to other major Canadian cities.

Brandon

Oshawa

Train Flight

Brandon to Oshawa

Updated: 29 May 2026

To reach Oshawa from Brandon, you must travel to Winnipeg (YWG) and fly to Toronto (YYZ), then take a train or bus to Oshawa. Alternatively, you can take the train from Winnipeg to Toronto and transfer to an Oshawa-bound train. This journey takes you from the prairies to the city of Oshawa.

Total Distance: 2,000 km driving distance; 1,500 km straight-line air distance.

Fastest Way

A connecting flight from Winnipeg to Toronto, then train to Oshawa, is the fastest.

Cheapest Way

Flying from Winnipeg is the most cost-effective and fastest method.

Compare Brandon to Oshawa Routes

	Train Connecting	Flight Connecting
Duration	37 hours	5 hours (total)
Avg Price	$500-$1,300	$350-$700
Operator	VIA Rail	Air Canada/WestJet
Route	Winnipeg to Toronto, then Toronto to Oshawa.	YWG to YYZ via Toronto, then train to Oshawa.
Tip	The train is a long but scenic way to see the country.	Connecting through Toronto is the most frequent route.

Travel Tips

Airport Transit
Taxis and ride-sharing services are available at the airport.
Weather
Oshawa can be very cold in winter; pack heavy winter gear.
Booking
Book flights in advance to secure the best rates.
Walking
Downtown Oshawa is walkable.

Safety Tips

Urban Safety
Oshawa is generally safe, but keep your belongings secure in tourist areas.
Winter Safety
Be careful on icy sidewalks during the winter months.
Emergency Services
Dial 911 for any emergencies.
Traffic
Avoid driving in downtown Oshawa; parking is limited.