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There are 10 ways to get from Chicago to Windsor by train, bus, car or plane

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  •  5h 43m

  1. Take the train from Chicago Union Station to Dearborn Wolverine

$56 - $77

Cheapest option

Bus  •  6h

  1. Take the bus from Chicago to Detroit "Greyhound"

$45 - $65

8 alternative options

Bus via Ann Arbor  •  7h 34m

  1. Take the bus from Chicago to Ann Arbor 2550

Drive  •  4h 45m

  1. Drive from Chicago to Windsor 457.6 km

$45 - $70

Fly Chicago Midway to Detroit  •  3h 50m

  1. Fly from Chicago Midway (MDW) to Detroit (DTW) MDW - DTW

$216 - $1,509

Fly Chicago O'Hare to Detroit  •  4h 9m

  1. Fly from Chicago O'Hare (ORD) to Detroit (DTW) ORD - DTW

$76 - $269

Train to South Bend, fly to Detroit  •  5h 39m

  1. Take the train from Van Buren St. to South Bend Airport
  2. Fly from South Bend (SBN) to Detroit (DTW) SBN - DTW

$250 - $521

Train to Milwaukee, fly to Detroit  •  5h 24m

  1. Take the train from Chicago Union Station to Milwaukee
  2. Fly from Milwaukee (MKE) to Detroit (DTW) MKE - DTW

$150 - $284

Fly Chicago O'Hare to Flint, bus  •  5h 46m

  1. Fly from Chicago O'Hare (ORD) to Flint (FNT) ORD - FNT
  2. Take the bus from Flint, MI to Detroit, MI

$210 - $519

Fly Chicago O'Hare to Toledo, bus  •  5h 19m

  1. Fly from Chicago O'Hare (ORD) to Toledo (TOL) ORD - TOL
  2. Take the bus from Toledo to Detroit

$219 - $415

Chicago to Windsor by train and bus

The journey time between Chicago and Windsor is around 7h 23m and covers a distance of around 451 km. The fastest journey normally takes 5h 37m. Operated by Amtrak and Southeast Michigan SMART, the Chicago to Windsor service departs from Chicago Union Station and arrives in Cass + Michigan. Typically 22 services run weekly, although weekend and holiday schedules can vary so check in advance.

Route overview

Average journey time:
7h 23m
Fastest journey time:
5h 37m
Journey distance:
451 km
Services per week:
22
Cheapest price:
$56
Carbon emissions:
24 kg CO2

First and last service

First service departs at:
07:05
Last service departs at:
17:50

The schedules shown below are for the next available departures.

Chicago to Windsor train and bus schedules

United States → Canada
Restricted

Travel safe during COVID-19

International entry into Canada from United States

  • Entry is restricted for citizens and permanent residents of United States
Show more details
Allowed for: Citizens and permanent residents

Restricted for: Foreign nationals

Show less

Conditions of entry into Canada from United States

  • Negative COVID-19 test issued at most 3 days prior for all arrivals by land or air 5 years of age or older
  • Travellers are required to submit their quarantine plan using ArriveCAN app prior to arrival
  • 14 day mandatory quarantine including 3 night pre-paid booking at a government authorised hotel at traveller's expense. COVID-19 test on arrival. Additional COVID-19 test on day 8 of quarantine
  • Negative COVID-19 result is required for quarantine release
  • Travellers with a certificate of vaccination are exempt from compulsory quarantine
This applies to arrivals from all countries, with no exceptions

Rules to follow in Canada

2m

Recommended

Recommended

Considerations leaving from United States

The official advice is to delay international travel until fully vaccinated

Frequently Asked Questions


No, entry into Canada from United States is currently restricted.

Explore options for future travel

Domestic travel is not restricted, but some conditions may apply

  • Face masks are recommended
  • There is a social distancing requirement of 2 metres
  • Domestic border crossings may be subject to approval, testing and quarantine
  • Regional restriction measures in place

Explore travel options

The national COVID-19 helpline number in Windsor is 1-833-784-4397.

Wearing a face mask on public transport in Windsor is recommended.

The social distance requirement in Windsor is 2 metres.

Make yourself known to an official member of staff and/or call the national coronavirus helpline number on 1-833-784-4397.

No, but conditions apply when returning to United States from Canada.

See options for return travel.

Last updated: 20 Jul 2021
Exceptions may apply, for full details: Government of Canada.

We're working around the clock to bring you the latest COVID-19 travel updates.
This information is compiled from official sources. To the best of our knowledge, it is correct as of the last update.
Visit Rome2rio travel advice for general help.

Questions & Answers

The cheapest way to get from Chicago to Windsor is to drive which costs $35 - $55 and takes 4h 45m.

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The quickest way to get from Chicago to Windsor is to fly which costs $170 - $1,200 and takes 3h 50m.

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Yes, there is a direct bus departing from Chicago and arriving at Detroit. Services depart twice daily, and operate every day. The journey takes approximately 6h.

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The distance between Chicago and Windsor is 383 km. The road distance is 457.6 km.

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The best way to get from Chicago to Windsor without a car is to train which takes 5h 43m and costs $45 - $65.

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It takes approximately 5h 43m to get from Chicago to Windsor, including transfers.

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Chicago to Windsor bus services, operated by Greyhound USA, depart from Chicago station.

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The best way to get from Chicago to Windsor is to train which takes 5h 43m and costs $45 - $65. Alternatively, you can bus, which costs $35 - $50 and takes 6h, you could also fly, which costs $170 - $1,200 and takes 3h 50m.

Mode details

The quickest flight from Chicago Midway Airport to Detroit Airport is the direct flight which takes 1h 5m.

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Chicago to Windsor bus services, operated by Greyhound USA, arrive at Detroit station.

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Map of how to get from Chicago to Windsor.
Launch map view
  • Distance: 383.4 km
  • Duration: 5h 43m

What companies run services between Chicago, IL, USA and Windsor, ON, Canada?

Amtrak operates a train from Chicago Union Station to Dearborn every 3 hours. Tickets cost $50 - $75 and the journey takes 4h 55m. Alternatively, Greyhound USA operates a bus from Chicago to Detroit twice daily. Tickets cost $45 - $65 and the journey takes 6h.

Airlines
Delta
Website
delta.com
Flights from Chicago Midway to Detroit
Ave. Duration
1h 13m
When
Every day
Estimated price
$45 - $250
Flights from Chicago O'Hare to Detroit
Ave. Duration
1h 24m
When
Every day
Estimated price
$40 - $200
Flights from South Bend to Detroit
Ave. Duration
1h 1m
When
Every day
Estimated price
$35 - $270
Flights from Milwaukee to Detroit
Ave. Duration
1h 11m
When
Every day
Estimated price
$50 - $270
Southwest Airlines
Website
southwest.com
Flights from Chicago Midway to Detroit
Ave. Duration
1h 5m
When
Every day
Estimated price
$120 - $410
American Airlines
Website
aa.com
Flights from Chicago O'Hare to Detroit
Ave. Duration
1h 25m
When
Every day
Estimated price
$100 - $430
Flights from Chicago O'Hare to Flint
Ave. Duration
1h 10m
When
Every day
Estimated price
$150 - $450
Flights from Chicago O'Hare to Toledo
Ave. Duration
1h 7m
When
Every day
Estimated price
$160 - $550
United Airlines
Website
united.com
Flights from Chicago O'Hare to Detroit
Ave. Duration
1h 16m
When
Every day
Estimated price
$120 - $490
Flights from Chicago O'Hare to Flint
Ave. Duration
1h 6m
When
Every day
Estimated price
$200 - $460
Train operators
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 Chicago Union Station to Dearborn
Ave. Duration
4h 55m
Frequency
Every 3 hours
Estimated price
$50 - $75
Schedules at
amtrak.com
Coach Seat
$50 - $75
Premium
$270 - $380
Flexi Coach Seat
$90 - $140
Business Seat
$95 - $140
Train from Chicago Union Station to Milwaukee
Ave. Duration
1h 29m
Frequency
Every 4 hours
Estimated price
$30 - $50
Schedules at
amtrak.com
Coach Seat
$30 - $50
Premium
$230 - $330
Flexi Coach Seat
$50 - $75
Business Seat
$45 - $70
South Shore Line
Phone
+1 219-926-5744
Website
mysouthshoreline.com
Train from Van Buren St. to South Bend Airport
Ave. Duration
2h 25m
Frequency
5 times a day
Estimated price
$16 - $19
Schedules at
mysouthshoreline.com
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 Chicago to Detroit
Ave. Duration
6h
Frequency
Twice daily
Estimated price
$45 - $65
Website
greyhound.com
Economy
$45 - $65
Flexible
$75 - $110
Bus from Toledo to Detroit
Ave. Duration
1h 10m
Frequency
3 times a day
Estimated price
$16 - $24
Website
greyhound.com
Economy
$16 - $24
Flexible
$35 - $55
FlixBus-us
Website
flixbus.com
Bus from Chicago to Ann Arbor
Ave. Duration
4h 10m
Frequency
5 times a week
Schedules at
flixbus.com
Indian Trails
Phone
+1 800-292-3831
Website
indiantrails.com
Bus from Flint, MI to Detroit, MI
Ave. Duration
1h 50m
Frequency
3 times a day
Estimated price
$12 - $18
Schedules at
indiantrails.com

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More Questions & Answers

Windsor is 1h ahead of Chicago. It is currently 1:09 AM in Chicago and 2:09 AM in Windsor.

Yes, the driving distance between Chicago to Windsor is 458 km. It takes approximately 4h 45m to drive from Chicago to Windsor.

Get driving directions

Delta and Southwest Airlines offer flights from Chicago Midway Airport to Detroit Airport.

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Book your Chicago to Windsor bus tickets online with Omio and Busbud.

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There are 105+ hotels available in Windsor. Prices start at $125 CAD per night.

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The best way to get from Chicago to Chicago Midway Airport is to subway which takes 23 min and costs $2 - $5.

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