There are 7 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 30 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

5 alternative options

Fly Detroit to Chicago O'Hare  •  3 h 50 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 30 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 2 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

Train  •  6 h 14 min

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

$52 - $132

Drive  •  4 h 44 min

  1. Drive from Windsor to Chicago 286.1 miles

$35 - $55

Questions & Answers

The cheapest way to get from Windsor to Chicago is to drive which costs $50 - $75 and takes 4 h 44 min.

More details

The quickest way to get from Windsor to Chicago is to fly which costs $160 - $350 and takes 3 h 30 min.

More details

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

Get driving directions

It takes approximately 3 h 30 min to get from Windsor to Chicago, including transfers.

More details

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

More details

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
When
Every day
Estimated price
$200 - $1,200
Southwest Airlines
Website
southwest.com
Flights from Detroit to Chicago Midway
Ave. Duration
1 h 7 min
When
Every day
Estimated price
$170 - $550
American Airlines
Website
aa.com
Flights from Detroit to Chicago O'Hare
Ave. Duration
1 h 30 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
United Airlines
Website
united.com
Flights from Detroit to Chicago O'Hare
Ave. Duration
1 h 20 min
When
Every day
Estimated price
$120 - $600
Train operators
Amtrak
Rome2rio's guide to Amtrak
Contact Details
Phone
+1 1-800-872-7245
Website
amtrak.com
Train from Detroit Amtrak to Chicago Union Station Amtrak
Ave. Duration
4 h 59 min
Frequency
3 times a day
Estimated price
$50 - $130
Website
amtrak.com
Coach Seat
$50 - $75
Flexi Coach Seat
$90 - $130
Business Coach Seat
$90 - $130
Room
$230 - $320
Bus operators
Greyhound USA
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
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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