- Must visit
Art Windsor-Essex
Windsor’s main art museum presents Canadian and international works, with a strong focus on contemporary and regional art.
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 traveling at rush hour.
The average ticket from Oakville, ON to Windsor, ON will cost around $69 if you buy it on the day, but the cheapest tickets can be found for only $69.
On Wed, Nov 04, we found 1 trains from Oakville, ON to Windsor, ON, including 1 direct services.
On Wed, Nov 04 the 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 .
On Wed, Nov 04 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.

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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 $47 (€39) 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 186 miles (300 km) distance in 3h 35m.
Plan this route
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, November 3. You can also manually refresh the results below to see updated train journeys.
| Provider | Departs | Duration | Arrives | Transfers | Tickets |
|---|---|---|---|---|---|
![]() | 12:09 AM Oakville, ON | 3h35 | 3:44 AM Windsor, ON | 0 transfersDirect | |
This is the last train of the day. | |||||
Find all the dates and times for this journey
Trains from Oakville, ON to Windsor, ON with Seajets. Night trains available on this route with Seajets. Use the details below to compare onboard facilities.
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.
Windsor’s main art museum presents Canadian and international works, with a strong focus on contemporary and regional art.
Local history museum inside the François Baby House, covering Windsor’s Indigenous, French, and borderland stories.
Hands-on science centre for families with interactive exhibits that make learning playful and accessible for children.
Signature riverfront promenade with skyline views, gardens, public art, and one of Windsor’s best urban walks.
Lively downtown park and festival space hosting events, concerts, and seasonal gatherings beside the riverfront.
Expansive waterfront park with lawns, paths, and broad Detroit River views, popular for relaxing and sunset walks.
Windsor-style pizza is the city’s signature pie, known for shredded pepperoni, canned mushrooms, Galati cheese, and often a sweeter sauce cut into squares.
A peameal bacon sandwich reflects Southwestern Ontario roots: cured cornmeal-coated pork on a bun, popular as a hearty local breakfast or lunch.
Poutine is widely loved in Windsor, especially after nights out, with fries, cheese curds, and gravy served across diners, pubs, and takeaway spots.
Well-known Lebanese restaurant serving shawarma, grilled meats, salads, and fresh pita in a relaxed, family-friendly setting.
Iconic casual spot famous for classic Windsor-style pizza. Long-standing local favourite for takeout and informal dine-in.
Refined steakhouse by Caesars Windsor known for premium steaks, seafood, and polished service in an upscale dining room.
Moderate for Canada. Hotels and dining are usually a bit cheaper than Toronto; transit is limited, so visitors may spend more on taxis or driving.
Tip 15-20% at restaurants before or after tax, depending on the bill. Taxis usually get 10-15%. Cafes often have tip jars or card prompts, but small tips are optional.
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.