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  • Greyhound USA
  • VIA Rail
  • Amtrak
  • Acela Express
  • Megabus
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  • Expedia

There are 10 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 27 min

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

$132 - $575

Cheapest option

Bus Greyhound USA  •  15 h 54 min

  1. Take the bus from Oakville, ON to Niagara Falls, ON 5 stops
  2. Take the bus from Buffalo, Ny to Springfield, Ma 255 / ...

$70 - $174

8 alternative options

Fly Billy Bishop Toronto City to Boston, bus  •  8 h 8 min

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

$112 - $410

Fly Toronto to Boston, bus  •  8 h 34 min

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

$129 - $487

Train, bus to Buffalo, fly to Boston, bus  •  9 h 45 min

  1. Take the train from Oakville to Niagara Falls
  2. Take the bus from Niagara Falls, ON to Buffalo Airport
  3. Fly from Buffalo (BUF) to Boston (BOS) BUF - BOS
  4. Take the bus from Boston, Ma to Hartford, Ct

$142 - $474

Fly Billy Bishop Toronto City to Newark, train  •  9 h 17 min

  1. Fly from Billy Bishop Toronto City (YTZ) to Newark (EWR) YTZ - EWR
  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

$217 - $705

Fly Toronto to New York La Guardia, train  •  9 h 41 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

$193 - $604

Train  •  15 h 9 min

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

$128 - $290

Bus via Syracuse, NY  •  16 h 53 min

  1. Take the bus from Toronto, ON to Syracuse, NY
  2. Take the bus from Syracuse, NY to Albany, NY
  3. Take the bus from Albany, NY to Springfield, MA

$99 - $190

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 $170 - $800 and takes 6 h 27 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 Niagara Falls, ON, Buffalo, Ny, Springfield, Ma and Main St and 750 Main St. The journey, including transfers, takes approximately 15 h 54 min.

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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 Station and Springfield Amtrak Station. The journey, including transfers, takes approximately 15 h 9 min.

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

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The best way to get from Oakville to Windsor without a car is to train which takes 15 h 9 min and costs $160 - $380.

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It takes approximately 6 h 27 min to get from Oakville to Windsor, including transfers.

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Oakville to Windsor bus services, operated by Megabus Canada, depart from Oakville, 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 train which takes 15 h 9 min and costs $160 - $380. Alternatively, you can bus, which costs $90 - $230 and takes 15 h 54 min.

Mode details

Map of how to get from Oakville to Windsor.
Launch map view
  • Distance: 376.4 miles
  • Duration: 6 h 27 min

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

You can take a train from Oakville to Windsor via Rochester, Rochester Amtrak Station, and Springfield Amtrak Station in around 15 h 9 min. Alternatively, you can take a bus from Oakville to Windsor via Niagara Falls, ON, Buffalo, NY, Buffalo, Ny, Springfield, Ma, Hartford, Ct, and Main St and 750 Main St in around 15 h 54 min.

Airlines
Air Canada
Website
aircanada.com
Flights from Toronto to Hartford
Ave. Duration
1 h 38 min
When
Every day
Estimated price
$260 - $1,500
Flights from Toronto to Hartford via Montreal
Ave. Duration
3 h 48 min
When
Every day
Estimated price
$260 - $1,500
Flights from Billy Bishop Toronto City to Boston via Montreal
Ave. Duration
3 h 51 min
When
Every day
Estimated price
$180 - $850
Flights from Toronto to Boston
Ave. Duration
1 h 33 min
When
Every day
Estimated price
$130 - $750
Flights from Toronto to Boston via Ottawa
Ave. Duration
3 h 23 min
When
Monday, Tuesday, Wednesday, Thursday, Friday and Sunday
Estimated price
$130 - $750
Flights from Toronto to Boston via Montreal
Ave. Duration
3 h 49 min
When
Every day
Estimated price
$130 - $750
Flights from Toronto to New York La Guardia
Ave. Duration
1 h 34 min
When
Every day
Estimated price
$110 - $650
United Airlines
Website
united.com
Flights from Toronto to Hartford
Ave. Duration
1 h 38 min
When
Monday, Tuesday, Wednesday, Thursday, Friday and Sunday
Estimated price
$260 - $1,500
Flights from Toronto to Hartford via Washington Dulles
Ave. Duration
3 h 47 min
When
Every day
Estimated price
$320 - $1,100
Flights from Toronto to Boston
Ave. Duration
1 h 33 min
When
Every day
Estimated price
$130 - $750
Flights from Toronto to Boston via Washington Dulles
Ave. Duration
3 h 46 min
When
Monday, Tuesday, Wednesday, Thursday, Friday and Sunday
Estimated price
$160 - $750
Flights from Buffalo to Boston via Newark
Ave. Duration
3 h 30 min
When
Wednesday
Estimated price
$170 - $900
Flights from Toronto to New York La Guardia
Ave. Duration
1 h 34 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
Flights from Billy Bishop Toronto City to Newark
Ave. Duration
1 h 30 min
When
Every day
Estimated price
$120 - $750
Delta
Website
delta.com
Flights from Toronto to Hartford via Detroit
Ave. Duration
4 h 10 min
When
Every day
Estimated price
$340 - $1,200
Flights from Toronto to Boston
Ave. Duration
1 h 56 min
When
Every day
Estimated price
$150 - $750
Flights from Buffalo to Boston
Ave. Duration
1 h 31 min
When
Every day
Estimated price
$130 - $750
Flights from Toronto to New York La Guardia
Ave. Duration
1 h 35 min
When
Every day
Estimated price
$110 - $700
WestJet
Website
westjet.com
Flights from Toronto to Hartford via Detroit
Ave. Duration
4 h 10 min
When
Every day
Estimated price
$340 - $1,200
Flights from Toronto to Boston
Ave. Duration
1 h 56 min
When
Every day
Estimated price
$150 - $750
Flights from Toronto to New York La Guardia
Ave. Duration
1 h 35 min
When
Every day
Estimated price
$110 - $700
American Airlines
Website
aa.com
Flights from Toronto to Hartford via Philadelphia
Ave. Duration
4 h 4 min
When
Every day
Estimated price
$210 - $1,200
Flights from Toronto to Boston via New York La Guardia
Ave. Duration
3 h 42 min
When
Monday, Tuesday, Wednesday, Thursday, Friday and Sunday
Estimated price
$120 - $800
Flights from Toronto to New York La Guardia
Ave. Duration
1 h 44 min
When
Every day
Estimated price
$110 - $650
JetBlue Airways
Website
jetblue.com
Flights from Buffalo to Boston
Ave. Duration
1 h 18 min
When
Every day
Estimated price
$100 - $550
Southwest Airlines
Website
southwest.com
Flights from Buffalo to Boston via Baltimore
Ave. Duration
3 h 30 min
When
Monday to Saturday
Estimated price
$220 - $800
Train operators
GO Transit
VIA Rail
Phone
+1 1 888 842-7245
Website
viarail.ca
Train from Oakville to Niagara Falls
Ave. Duration
1 h 32 min
Frequency
Once daily
Estimated price
$35 - $80
Website
viarail.ca
Escape
$18 - $40
Economy
$35 - $55
EconomyPlus
$55 - $80
Business
$50 - $75
Train from Oakville to Rochester
Ave. Duration
5 h 9 min
Frequency
Once daily
Estimated price
$50 - $100
Website
viarail.ca
Escape
$30 - $55
Economy
$50 - $75
EconomyPlus
$70 - $100
Business
$80 - $110
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
+1 215-856-7924
Website
amtrak.com
Train from New York Penn Station to New Haven Union Station
Ave. Duration
1 h 39 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
+1 215-856-7924
Website
amtrak.com
Train from New Haven Union Station to Windsor Amtrak
Ave. Duration
52 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 Station to Springfield Amtrak Station
Ave. Duration
7 h 35 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 3 hours
Estimated price
$16 - $40
Website
greyhound.com
Economy
$16 - $24
Flexible
$28 - $40
Bus from Niagara Falls, On to Buffalo Airport
Ave. Duration
2 h 35 min
Frequency
4 times a day
Estimated price
$10 - $23
Website
greyhound.com
Economy
$10 - $15
Flexible
$18 - $23
Bus from Buffalo, Ny to Springfield, Ma
Ave. Duration
9 h 25 min
Frequency
3 times a day
Estimated price
$40 - $110
Website
greyhound.com
Economy
$40 - $70
Flexible
$80 - $110
Megabus Canada
Phone
1-866-488-4452
Email
canada-info@coachcanada.com
Website
ca.megabus.com
Bus from Niagara Falls, ON to Buffalo Airport
Ave. Duration
1 h 15 min
Frequency
4 times a day
Estimated price
$9 - $15
Book at
megabus.ca
Bus from Oakville, ON to Niagara Falls, ON
Ave. Duration
1 h 25 min
Frequency
Once daily
Estimated price
$12 - $18
Book at
megabus.ca
Greyhound Canada
Phone
+1 1-800-661-8747
Email
Canada.info@greyhound.ca
Website
greyhound.ca
Bus from Toronto, ON to Syracuse, NY
Ave. Duration
6 h 5 min
Frequency
Once daily
Estimated price
$26 - $120
Website
Greyhound.ca
Advanced Purchase
$26 - $40
Online Fare
$30 - $55
Standard Fare
$45 - $65
Refundable
$50 - $75
Trailways New York
Peter Pan Bus Lines
Phone
1-800-343-9999
Website
peterpanbus.com
Bus from Albany, NY to Springfield, MA
Ave. Duration
2 h 5 min
Frequency
3 times a day
Estimated price
$15 - $35
Website
peterpanbus.com

Want to know more about travelling around United States

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More Questions & Answers

The quickest flight from Toronto Airport to Hartford Airport is the direct flight which takes 1 h 38 min.

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Oakville to Windsor bus services, operated by Greyhound USA, arrive at Springfield, Ma 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

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

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There are 95+ hotels available in Windsor. Prices start at $67 USD per night.

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