There are 8 ways to get from Oakville to Windsor by train, plane, bus or car

Select an option below to see step-by-step directions and to compare ticket prices and travel times in Rome2rio's travel planner.

Recommended option

Train to Toronto, fly to Hartford  •  6 h 10 min

  1. Take the train from Oakville to Toronto
  2. Fly from Toronto (YYZ) to Hartford (BDL) YYZ - BDL

$147 - $622

Cheapest option

Train, bus  •  14 h 30 min

  1. Take the train from Oakville to Rochester VIA Rail
  2. Take the bus from Rochester, Ny to Springfield, Ma 255 / ...

$89 - $232

6 alternative options

Fly Toronto to Boston, bus  •  7 h 22 min

  1. Fly from Toronto (YYZ) to Boston (BOS) YYZ - BOS
  2. Take the bus from Boston, Ma to Hartford, Ct

$144 - $534

Fly Billy Bishop Toronto City to Boston, bus  •  7 h 17 min

  1. Fly from Billy Bishop Toronto City (YTZ) to Boston (BOS) YTZ - BOS
  2. Take the bus from Boston, Ma to Hartford, Ct

$128 - $457

Fly Toronto to New York La Guardia, train  •  9 h 13 min

  1. Fly from Toronto (YYZ) to New York La Guardia (LGA) YYZ - LGA
  2. Take the train from New York Penn Station to New Haven Union Station
  3. Take the train from New Haven Union Station to Windsor Amtrak

$208 - $651

Bus  •  15 h

  1. Take the bus from Toronto, On to New York, NY 5593
  2. Take the bus from New York, Ny to Hartford, Ct 2008 / ...

$98 - $157

Train  •  15 h 12 min

  1. Take the train from Oakville to Rochester VIA Rail
  2. Take the train from Rochester Amtrak to Springfield Amtrak Lake Shore Limited

$109 - $292

Drive  •  8 h 3 min

  1. Drive from Oakville to Windsor 466.4 miles

$60 - $90

Questions & Answers

The cheapest way to get from Oakville to Windsor is to drive which costs $80 - $120 and takes 8 h 3 min.

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The quickest way to get from Oakville to Windsor is to train and fly which costs $180 - $850 and takes 6 h 10 min.

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No, there is no direct bus from Oakville to Windsor station. However, there are services departing from Oakville, ON and arriving at Mechanic St and Opp R R Station via Toronto, On, New York, Ny and Main St and 750 Main St. The journey, including transfers, takes approximately 15 h.

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No, there is no direct train from Oakville to Windsor. However, there are services departing from Oakville and arriving at Windsor Amtrak via Rochester Amtrak and Springfield Amtrak. The journey, including transfers, takes approximately 15 h 12 min.

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The distance between Oakville and Windsor is 602 km. The road distance is 746.2 km.

Get driving directions

The best way to get from Oakville to Windsor without a car is to train and bus which takes 14 h 30 min and costs $110 - $300.

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It takes approximately 6 h 10 min to get from Oakville to Windsor, including transfers.

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Oakville to Windsor bus services, operated by Trailways New York, depart from Toronto, On station.

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Oakville to Windsor train services, operated by VIA Rail, depart from Oakville station.

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The best way to get from Oakville to Windsor is to bus which takes 15 h and costs $120 - $210. Alternatively, you can train, which costs $140 - $380 and takes 15 h 12 min.

Mode details

Map of how to get from Oakville to Windsor.
Launch map view
  • Distance: 376.4 miles
  • Duration: 6 h 10 min

What companies run services between Oakville, ON, Canada and Windsor, CT, USA?

You can take a bus from Oakville to Windsor via Toronto, ON, Toronto, On, New York, NY, New York, Ny, Hartford, Ct, and Main St and 750 Main St in around 15 h. Alternatively, you can take a train from Oakville to Windsor via Rochester, Rochester Amtrak, and Springfield Amtrak in around 15 h 12 min.

Airlines
Air Canada
Website
aircanada.com
Flights from Toronto to Hartford
Ave. Duration
1 h 43 min
When
Every day
Estimated price
$260 - $1,500
Flights from Toronto to Hartford via Montreal
Ave. Duration
3 h 53 min
When
Every day
Estimated price
$260 - $1,500
Flights from Toronto to Boston
Ave. Duration
1 h 32 min
When
Every day
Estimated price
$130 - $750
Flights from Toronto to Boston via Montreal
Ave. Duration
3 h 31 min
When
Every day
Estimated price
$130 - $750
Flights from Billy Bishop Toronto City to Boston via Montreal
Ave. Duration
3 h 39 min
When
Every day
Estimated price
$180 - $850
Flights from Toronto to New York La Guardia
Ave. Duration
1 h 29 min
When
Every day
Estimated price
$110 - $650
United Airlines
Website
united.com
Flights from Toronto to Hartford
Ave. Duration
1 h 43 min
When
Every day
Estimated price
$260 - $1,500
Flights from Toronto to Hartford via Washington Dulles
Ave. Duration
3 h 58 min
When
Every day
Estimated price
$320 - $1,100
Flights from Toronto to Hartford via Newark
Ave. Duration
3 h 42 min
When
Monday, Tuesday, Wednesday, Thursday and Saturday
Estimated price
$260 - $1,500
Flights from Toronto to Boston
Ave. Duration
1 h 32 min
When
Every day
Estimated price
$130 - $750
Flights from Toronto to Boston via Newark
Ave. Duration
3 h 39 min
When
Monday, Tuesday, Wednesday, Thursday and Sunday
Estimated price
$160 - $750
Flights from Toronto to New York La Guardia
Ave. Duration
1 h 29 min
When
Every day
Estimated price
$110 - $650
Delta
Website
delta.com
Flights from Toronto to Hartford via Detroit
Ave. Duration
4 h 12 min
When
Every day
Estimated price
$340 - $1,200
Flights from Toronto to Boston
Ave. Duration
1 h 55 min
When
Every day
Estimated price
$150 - $750
Flights from Toronto to New York La Guardia
Ave. Duration
1 h 31 min
When
Every day
Estimated price
$110 - $700
WestJet
Website
westjet.com
Flights from Toronto to Hartford via Detroit
Ave. Duration
4 h 12 min
When
Every day
Estimated price
$340 - $1,200
Flights from Toronto to Boston
Ave. Duration
1 h 55 min
When
Every day
Estimated price
$150 - $750
Flights from Toronto to New York La Guardia
Ave. Duration
1 h 31 min
When
Every day
Estimated price
$110 - $700
American Airlines
Website
aa.com
Flights from Toronto to Hartford via Philadelphia
Ave. Duration
3 h 34 min
When
Every day
Estimated price
$210 - $1,200
Flights from Toronto to New York La Guardia
Ave. Duration
1 h 40 min
When
Every day
Estimated price
$110 - $650
Porter Airlines
Website
flyporter.com
Flights from Billy Bishop Toronto City to Boston
Ave. Duration
1 h 35 min
When
Every day
Estimated price
$110 - $600
Train operators
VIA Rail
Phone
+1 1 888 842-7245
Website
viarail.ca
Train from Oakville to Toronto
Ave. Duration
22 min
Frequency
Every 30 minutes
Estimated price
$20 - $55
Website
viarail.ca
Escape
$20 - $29
Economy
$23 - $35
Economy Plus
$35 - $55
Business
$30 - $45
Business Plus/Sleeper
$55 - $85
Train from Oakville to Rochester
Ave. Duration
5 h 9 min
Frequency
Every 3 hours
Estimated price
$30 - $110
Website
viarail.ca
Escape
$30 - $50
Economy
$50 - $70
Economy Plus
$75 - $110
Business
$70 - $100
Business Plus/Sleeper
$120 - $180
Amtrak Acela Express

Amtrak is a rail service that connects the US and three Canadian provinces. Covering 21,000 route miles (34,000km) Amtrak operates more than 300 trains daily. These medium and long distance intercity services operate at speeds of up to 240km/h, to more than 500 destinations. Founded in 1971, it is based in Washington, D.C. and offers four classes of travel: First Class, Sleeper, Business and Coach. Ticket fares are divided into five subclasses: Saver, Value, Flexible, Business and Premium. Amtrak trains are known for their wide seats, plug-in power, big windows and storage capabilities.

Rome2rio's guide to Amtrak Acela Express
Contact Details
Phone
+1 1-800-872-7245
Website
amtrak.com
Train from New York Penn Station to New Haven Union Station
Ave. Duration
1 h 37 min
Frequency
Hourly
Estimated price
$70 - $190
Website
amtrak.com
Business Seat
$70 - $170
First Class Seat
$140 - $190
Amtrak

Amtrak is a rail service that connects the US and three Canadian provinces. Covering 21,000 route miles (34,000km) Amtrak operates more than 300 trains daily. These medium and long distance intercity services operate at speeds of up to 240km/h, to more than 500 destinations. Founded in 1971, it is based in Washington, D.C. and offers four classes of travel: First Class, Sleeper, Business and Coach. Ticket fares are divided into five subclasses: Saver, Value, Flexible, Business and Premium. Amtrak trains are known for their wide seats, plug-in power, big windows and storage capabilities.

Rome2rio's guide to Amtrak
Contact Details
Phone
+1 1-800-872-7245
Website
amtrak.com
Train from New Haven Union Station to Windsor Amtrak
Ave. Duration
50 min
Frequency
Every 4 hours
Estimated price
$23 - $45
Website
amtrak.com
Coach Seat
$23 - $35
Flexi Coach Seat
$40 - $60
Business Coach Seat
$30 - $45
Room
$130 - $190
Train from Rochester Amtrak to Springfield Amtrak
Ave. Duration
7 h 38 min
Frequency
Once daily
Estimated price
$55 - $150
Website
amtrak.com
Coach Seat
$55 - $85
Flexi Coach Seat
$100 - $150
Business Coach Seat
$100 - $150
Room
$250 - $350
Bus operators
Greyhound USA

Greyhound is a leading bus company based in Dallas, Texas, serving over 3800 destinations across North America, Mexico and Canada. Greyhound carries around 18 million passengers a year who travel 5.4 billion miles (8.6 billion km) a year on their fleet of around 1700 vehicles. For travel flexibility, you can board or get off a Greyhound bus at official Greyhound stations, partner stations and curbside stops. There are around 230 Greyhound stations across the US where you can both catch your bus and buy tickets, that are also available on the official website and via the mobile app.

Rome2rio's guide to Greyhound USA
Contact Details
Phone
+1 214-849-8100/1-800-231-2222
Email
ifsr@greyhound.com
Website
greyhound.com
Bus from Boston, Ma to Hartford, Ct
Ave. Duration
1 h 50 min
Frequency
Every 30 minutes
Estimated price
$16 - $40
Website
greyhound.com
Economy
$16 - $24
Flexible
$28 - $40
Bus from Rochester, Ny to Springfield, Ma
Ave. Duration
7 h 40 min
Frequency
Every 30 minutes
Estimated price
$35 - $90
Website
greyhound.com
Economy
$35 - $60
Flexible
$65 - $90
Bus from New York, Ny to Hartford, Ct
Ave. Duration
2 h 29 min
Frequency
Every 30 minutes
Estimated price
$17 - $40
Website
greyhound.com
Economy
$17 - $26
Flexible
$30 - $40
Trailways New York
Phone
(800) 858-8555
Website
trailwaysny.com
Bus from Toronto, On to New York, NY
Ave. Duration
10 h
Frequency
Every 2 hours
Estimated price
$70 - $100
Schedules at
trailwaysny.com
Greyhound Canada
Phone
+1 1-800-661-8747
Email
Canada.info@greyhound.ca
Website
greyhound.ca
Bus from Toronto, ON to New York, NY
Ave. Duration
10 h 15 min
Frequency
Once daily
Estimated price
$40 - $110
Website
Greyhound.ca
Advanced Purchase
$40 - $65
Online Fare
$55 - $85
Standard Fare
$70 - $110
Refundable
$80 - $120

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More Questions & Answers

The quickest flight from Toronto Airport to Hartford Airport is the direct flight which takes 1 h 43 min.

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Oakville to Windsor bus services, operated by Greyhound USA, arrive at Hartford, Ct station.

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Oakville to Windsor train services, operated by Amtrak, arrive at Springfield Amtrak station.

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Yes, the driving distance between Oakville to Windsor is 746 km. It takes approximately 8 h 3 min to drive from Oakville to Windsor.

Get driving directions

American Airlines, Delta, United Airlines and Air Canada offer flights from Toronto Airport to Hartford Airport.

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There are 97+ hotels available in Windsor. Prices start at $69 USD per night.

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