- Must visit
Art Windsor-Essex
A leading local art gallery with Canadian and international works, plus changing exhibitions in a modern waterfront building.
The best way to find a cheap train ticket from Oakville, ON to Windsor, ON is to book your journey as far in advance as possible and to avoid travelling at rush hour.
The average ticket from Oakville, ON to Windsor, ON will cost around £51 if you buy it on the day, but you can find cheap train tickets today for only £51.
On Wed 04 Nov, we found 1 trains from Oakville, ON to Windsor, ON, including 1 direct services.
These direct trains cover the 300 km distance in an average of 3 h 35 m but if you time it right, some trains will get you there in just 3 h 35 m .
The slowest trains will take 3 h 35 m and usually involve a change or two along the way, but you might be able to save a few pennies if you’re on a budget.

|
| ||||||||||||

|
| ||||||||||||
Trains from Oakville, ON to Windsor, ON run on average 4 times per day, taking around 3h 50m. Cheap train tickets for this journey start at £35 if you book in advance.
There are 4 trains per day. The earliest train runs at 05:35, the last at 21:30. The fastest train covers the 300 km distance in 3h 35m.
Distance 300 km |
Average train duration 3h 50m |
Cheapest ticket price £35 |
Trains per day 4 |
Direct trains 4 |
Fastest train 3h 35m |
First train 5:35 |
Last train 21:30 |
Cheapest Month Sept |
Cheapest Day Sat |
High Season Apr - Jun |
Low Season Jul - Sept |
Best time to book 35 days |
Use these quick route answers to check fares, travel time, departure options, and direct services before booking from Oakville, ON to Windsor, ON.
The table below shows live departures for Oakville, ON to Windsor, ON trains for tomorrow, Tuesday 3 November. You can also manually refresh the results below to see updated train journeys.
| Provider | Departs | Duration | Arrives | Changes | Tickets |
|---|---|---|---|---|---|
![]() | 0:09 Oakville, ON | 3h35 | 3:44 Windsor, ON | 0 changesdirect | |
This is the last train of the day. | |||||
Find all the dates and times for this journey
Review the details behind your booking, from operators and ticket rules to luggage, onboard amenities, accessibility, and route-specific travel policies.
Discover the best of Windsor, ON — top attractions, local food, transport tips, budget advice, and currency essentials. Plan your perfect Windsor, ON trip today.
A leading local art gallery with Canadian and international works, plus changing exhibitions in a modern waterfront building.
A community museum in Sandwich exploring local, Black, and military history through exhibits in a restored historic setting.
A former distillery estate museum in Walkerville, presenting the Hiram Walker story, architecture, and neighbourhood heritage.
A long waterfront park with gardens, memorials, sculptures, and skyline views across the Detroit River.
A historic neighbourhood known for early 20th-century homes, church landmarks, and a walkable village atmosphere.
A large urban park with trails, formal gardens, ponds, sports areas, and family-friendly green space close to the city centre.
Cool-climate Chardonnay from Sonoma County, often made around Windsor, prized for balanced fruit and bright acidity shaped by Pacific influence.
Pinot Noir from nearby Russian River Valley and Sonoma Coast, a regional speciality known for elegant red fruit and earthy notes.
Zinfandel is a classic Sonoma wine, typically bold and spicy, reflecting the county’s long winemaking history and warm inland vineyards.
Modern wine country restaurant in Windsor Town Green, known for seasonal Californian cooking, wood-fired dishes and a polished but relaxed setting.
Lively Mexican restaurant on the Town Green serving tacos, enchiladas and margaritas in a casual, dependable setting popular with locals.
Casual local favourite for Thai curries, noodle dishes and stir-fries, offering generous portions and an easy neighbourhood atmosphere.
Moderate for Canada: meals and coffee are fairly priced, but hotels and car-dependent travel can raise trip costs versus smaller nearby towns.
Tip 15-20% in restaurants if service is not included. In cafés, rounding up or leaving $1 is common. Taxi drivers usually get 10-15%.
Get destination-focused answers for the end of your trip, including what to do, when to go, practical entry details, and tips for making the most of your time in Windsor, ON.
Find answers to the most common questions about traveling from Oakville, ON to Windsor, ON by train. From journey times and ticket prices to direct connections, first and last departures, and even whether the route is scenic, our FAQs cover everything you need to plan your trip. Whether you’re looking for the fastest train, the cheapest option, or tips for making the most of your visit at Windsor, ON, this guide helps you travel smarter and with confidence.

Most Oakville, ON to Windsor, ON trains use the Oakville to Windsor station pair. Use this guide to compare Oakville, ON and Windsor, ON train stations on this route, check city-centre transport, alongside checking practicalities like train station facilities and services.
Oakville has practical services for this route, including Parking, Dining, ATM, Accessibility, WC and Car Rental.
Food and drink options are available at Oakville.
ATMs are available at Oakville.
Available at Oakville: Parking, WC.
Available at Oakville: Car Rental.
Accessibility facilities are available at Oakville.
Windsor is 2 km from Windsor city centre. Public transport options include:
Windsor has practical services for this route, including Dining and Accessibility.
Food and drink options are available at Windsor.
Accessibility facilities are available at Windsor.
Check train stations information for Oakville, ON and Windsor, ON, including where trains depart and arrive on this route.
Here are some other resources that might have the information you need