- Recommended
Oakville Galleries at Gairloch Gardens
Large public gallery in Gairloch Gardens presenting changing contemporary art exhibitions in a lakeside historic setting.
The best way to find a cheap train ticket from Windsor, ON to Oakville, ON is to book your journey as far in advance as possible and to avoid travelling at rush hour.
The average ticket from Windsor, ON to Oakville, ON will cost around £51 if you buy it on the day, but you can find cheap train tickets today for only £48.
On Tue 03 Nov, we found 2 trains from Windsor, ON to Oakville, ON, including 2 direct services.
These direct trains cover the 300 km distance in an average of 3 h 56 m but if you time it right, some trains will get you there in just 3 h 44 m .
The slowest trains will take 4 h 8 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.

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Trains from Windsor, ON to Oakville, ON run on average 5 times per day, taking around 6h 21m. 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 41m.
Distance 300 km |
Average train duration 6h 21m |
Cheapest ticket price £35 |
Trains per day 5 |
Direct trains 4 |
Fastest train 3h 41m |
First train 5:35 |
Last train 21:30 |
Cheapest Month Sept |
Cheapest Day Fri |
High Season Jul - Sept |
Low Season Apr - Jun |
Best time to book 21 days |
Use these quick route answers to check fares, travel time, departure options, and direct services before booking from Windsor, ON to Oakville, ON.
The table below shows live departures for Windsor, ON to Oakville, ON trains for today, Monday 2 November. You can also manually refresh the results below to see updated train journeys.
| Provider | Departs | Duration | Arrives | Changes | Tickets |
|---|---|---|---|---|---|
![]() | 10:35 Windsor, ON | 4h08 | 14:43 Oakville, ON | 0 changesdirect | |
![]() | 21:40 Windsor, ON | 3h44 | 1:24 Oakville, 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 Oakville, ON — top attractions, local food, transport tips, budget advice, and currency essentials. Plan your perfect Oakville, ON trip today.
Large public gallery in Gairloch Gardens presenting changing contemporary art exhibitions in a lakeside historic setting.
Contemporary art space in Centennial Square featuring rotating exhibitions and public programmes in the heart of downtown Oakville.
Local history museum in a heritage estate exploring Oakville’s founding family, domestic life, and lakeside past.
Charming heritage district with boutiques, lake views, and preserved streetscapes, ideal for strolling and experiencing Oakville’s historic core.
Lakeside park with gardens, lawns, and shoreline paths beside an art gallery, popular for peaceful walks and photography.
Waterfront park with open lawns, picnic areas, and lake views, well liked for sunsets, family visits, and relaxed walks.
Icewine is a regional speciality made from naturally frozen grapes, producing an intensely sweet dessert wine closely linked with Ontario wine country.
VQA Ontario Chardonnay is widely poured locally, reflecting the nearby Niagara Peninsula and a cool-climate style valued across the region.
Peameal bacon on a bun is a Southern Ontario classic of wet-cured pork rolled in cornmeal, usually served in a soft bun with mustard.
Refined lakeside dining in Bronte with steaks, seafood and polished service. A strong choice for a special meal with harbour views.
Popular local bakery and café serving pastries, cakes, breads and light savoury dishes in a relaxed all-day setting.
Established downtown Oakville restaurant known for hearty pub fare, brunch and oysters in a lively, traditional setting.
Oakville is pricier than many Canadian suburbs, with higher hotel and dining costs; local buses are modestly priced and Toronto day trips can add to budgets.
Tip 15-20% in restaurants if service is not included. Round up or add about 10% for taxis. Small tips are appreciated in cafés, but not essential.
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 Oakville, ON.
Find answers to the most common questions about traveling from Windsor, ON to Oakville, 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 Oakville, ON, this guide helps you travel smarter and with confidence.

Most Windsor, ON to Oakville, ON trains use the Windsor to Oakville station pair. Use this guide to compare Windsor, ON and Oakville, ON train stations on this route, check city-centre transport, alongside checking practicalities like train station facilities and services.
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.
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.
Check train stations information for Windsor, ON and Oakville, ON, including where trains depart and arrive on this route.
Here are some other resources that might have the information you need