There are 8 ways to get from Windsor to Chicago by plane, bus, train 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

Fly Detroit to Chicago Midway  •  3 h 29 min

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

$124 - $266

Cheapest option

Bus  •  5 h 49 min

  1. Take the bus from Windsor, ON to Chicago, IL 5515 / ...

$28 - $70

6 alternative options

Fly Detroit to Chicago O'Hare  •  3 h 55 min

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

$114 - $317

Bus to Toledo, fly to Chicago O'Hare  •  4 h 32 min

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

$130 - $368

Fly Detroit to South Bend, bus  •  5 h 3 min

  1. Fly from Detroit (DTW) to South Bend (SBN) DTW - SBN
  2. Take the bus from South Bend, In to Chicago, Il

$217 - $1,237

Bus to Flint, fly to Chicago O'Hare  •  5 h 54 min

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

$93 - $417

Train  •  6 h 3 min

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

$47 - $132

Drive  •  4 h 44 min

  1. Drive from Windsor to Chicago 286.1 miles

$35 - $55

Questions & Answers

Yes, there is a direct bus departing from Windsor, ON and arriving at Chicago, IL. Services depart every three hours, and operate every day. The journey takes approximately 5 h 49 min.

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The distance between Windsor and Chicago is 383 km. The road distance is 457.8 km.

Get driving directions

The best way to get from Windsor to Chicago without a car is to bus which takes 5 h 49 min and costs .

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It takes approximately 3 h 29 min to get from Windsor to Chicago, including transfers.

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

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The best way to get from Windsor to Chicago is to fly which takes 3 h 29 min and costs . Alternatively, you can bus, which costs and takes 5 h 49 min, you could also train, which costs and takes 6 h 3 min.

Mode details

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

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Windsor to Chicago bus services, operated by Greyhound Canada, arrive at Chicago, IL station.

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Chicago is 1 h behind Windsor. It is currently 8:12 AM in Windsor and 7:12 AM in Chicago.

Yes, the driving distance between Windsor to Chicago is 458 km. It takes approximately 4 h 44 min to drive from Windsor to Chicago.

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Map of how to get from Windsor to Chicago.
Launch map view
  • Distance: 239.6 miles
  • Duration: 3 h 29 min

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

Southwest Airlines and Delta fly from Windsor to Chicago every 4 hours. Alternatively, Greyhound Canada operates a bus from Windsor to Chicago 4 times a day. Tickets cost $28 - $70 and the journey takes 5 h 49 min. Two other operators also service this route.

Airlines
Delta
Website
delta.com
Flights from Detroit to Chicago Midway
Ave. Duration
1 h 15 min
When
Every day
Estimated price
$120 - $460
Flights from Detroit to Chicago O'Hare
Ave. Duration
1 h 25 min
When
Every day
Estimated price
$120 - $460
Flights from Detroit to South Bend
Ave. Duration
1 h 4 min
When
Every day
Estimated price
$200 - $1,200
American Airlines
Website
aa.com
Flights from Detroit to Chicago O'Hare
Ave. Duration
1 h 32 min
When
Every day
Estimated price
$120 - $460
Flights from Toledo to Chicago O'Hare
Ave. Duration
1 h 17 min
When
Every day
Estimated price
$160 - $460
Flights from Flint to Chicago O'Hare
Ave. Duration
1 h 19 min
When
Every day
Estimated price
$100 - $650
United Airlines
Website
united.com
Flights from Detroit to Chicago O'Hare
Ave. Duration
1 h 24 min
When
Every day
Estimated price
$120 - $600
Flights from Flint to Chicago O'Hare
Ave. Duration
1 h 13 min
When
Every day
Estimated price
$130 - $750
Southwest Airlines
Website
southwest.com
Flights from Detroit to Chicago Midway
Ave. Duration
1 h 8 min
When
Every day
Estimated price
$170 - $550
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 1-800-872-7245
Website
amtrak.com
Train from Dearborn Amtrak to Chicago Union Station
Ave. Duration
4 h 41 min
Frequency
3 times a day
Estimated price
$45 - $130
Website
amtrak.com
Coach Seat
$45 - $75
Flexi Coach Seat
$85 - $130
Business Coach Seat
$90 - $130
Room
$230 - $320
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 Detroit, Mi to Toledo, Oh
Ave. Duration
1 h 10 min
Frequency
Every 15 minutes
Estimated price
$12 - $28
Website
greyhound.com
Economy
$12 - $19
Flexible
$22 - $28
Bus from South Bend, In to Chicago, Il
Ave. Duration
1 h 10 min
Frequency
Every 3 hours
Estimated price
$15 - $35
Website
greyhound.com
Economy
$15 - $23
Flexible
$27 - $35
Bus from Windsor, On to Chicago, Il
Ave. Duration
7 h 5 min
Frequency
Every 4 hours
Estimated price
$30 - $80
Website
greyhound.com
Economy
$30 - $55
Flexible
$60 - $80
Indian Trails
Phone
+1 800-292-3831
Website
indiantrails.com
Bus from Detroit, MI to Flint
Ave. Duration
1 h 43 min
Frequency
Once daily
Estimated price
$12 - $16
Schedules at
indiantrails.com
Book at
webstore.indiantrails.com
Greyhound Canada
Phone
+1 1-800-661-8747
Email
Canada.info@greyhound.ca
Website
greyhound.ca
Bus from Windsor, ON to Chicago, IL
Ave. Duration
5 h 49 min
Frequency
4 times a day
Estimated price
$28 - $70
Website
Greyhound.ca
Advanced Purchase
$28 - $45
Online Fare
$35 - $60
Standard Fare
$45 - $70
Refundable
$50 - $80

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More Questions & Answers

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

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Book your Windsor to Chicago bus tickets online with Busbud.

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There are 580+ hotels available in Chicago. Prices start at $103 USD per night.

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The best way to get from Windsor to Detroit Airport is to line 261 bus which takes 49 min and costs .

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