Bus Chicago to Windsor, ON - Compare all Companies

Compare all timetables for the bus from Chicago to Windsor, ON

Here is a selection of the cheapest bus trips from the schedule from Chicago to Windsor, ON from various bus operators like Greyhound US or FlixBus for the next days.

today

tomorrow

Wednesday

Thursday

Friday

$42

Saturday

$39

Sunday

$46

Cheapest bus trips Friday
BertCompanyCountOneCompanyName	Duration	Departure time	From	Departure	Arrival time	To	Destination	Seat classes	Price
Greyhound US	9h 25m	6:30 AM	Chicago	Downtown Bus Station	4:55 PM	Windsor, ON	International Transit Terminal	Economy	$42	A Bus from Greyhound US goes from Downtown Bus Station, Chicago (USA) at 9/11/2026 6:30:00 AM to International Transit Terminal, Windsor, ON (Canada) arriving at 9/11/2026 4:55:00 PM. 50 Economy ticket for $42 per person are available. Travel duration is 9h 25m
Greyhound US	7h 30m	3:55 PM	Chicago	Downtown Bus Station	12:25 AM	Windsor, ON	International Transit Terminal	Economy	$42	A Bus from Greyhound US goes from Downtown Bus Station, Chicago (USA) at 9/11/2026 3:55:00 PM to International Transit Terminal, Windsor, ON (Canada) arriving at 9/12/2026 12:25:00 AM. 50 Economy ticket for $42 per person are available. Travel duration is 7h 30m
Greyhound US	11h 50m	11:35 PM	Chicago	Downtown Bus Station	12:25 PM	Windsor, ON	International Transit Terminal	Economy	$42	A Bus from Greyhound US goes from Downtown Bus Station, Chicago (USA) at 9/11/2026 11:35:00 PM to International Transit Terminal, Windsor, ON (Canada) arriving at 9/12/2026 12:25:00 PM. 50 Economy ticket for $42 per person are available. Travel duration is 11h 50m
FlixBus	18h 20m	5:05 PM	Chicago	95th Red Line Station	12:25 PM	Windsor, ON	International Transit Terminal	Economy	$59	A Bus from FlixBus goes from 95th Red Line Station, Chicago (USA) at 9/11/2026 5:05:00 PM to International Transit Terminal, Windsor, ON (Canada) arriving at 9/12/2026 12:25:00 PM. 50 Economy ticket for $59 per person are available. Travel duration is 18h 20m
FlixBus	10h 30m	5:25 AM	Chicago	95th Red Line Station	4:55 PM	Windsor, ON	International Transit Terminal	Economy	$59	A Bus from FlixBus goes from 95th Red Line Station, Chicago (USA) at 9/11/2026 5:25:00 AM to International Transit Terminal, Windsor, ON (Canada) arriving at 9/11/2026 4:55:00 PM. 50 Economy ticket for $59 per person are available. Travel duration is 10h 30m

Cheapest bus trips Saturday
BertCompanyCountOneCompanyName	Duration	Departure time	From	Departure	Arrival time	To	Destination	Seat classes	Price
FlixBus	9h 10m	9:30 AM	Chicago	Downtown Bus Station	7:40 PM	Windsor, ON	International Transit Terminal	Economy	$39	A Bus from FlixBus goes from Downtown Bus Station, Chicago (USA) at 9/12/2026 9:30:00 AM to International Transit Terminal, Windsor, ON (Canada) arriving at 9/12/2026 7:40:00 PM. 50 Economy ticket for $39 per person are available. Travel duration is 9h 10m
Greyhound US	7h 30m	3:55 PM	Chicago	Downtown Bus Station	12:25 AM	Windsor, ON	International Transit Terminal	Economy	$39	A Bus from Greyhound US goes from Downtown Bus Station, Chicago (USA) at 9/12/2026 3:55:00 PM to International Transit Terminal, Windsor, ON (Canada) arriving at 9/13/2026 12:25:00 AM. 50 Economy ticket for $39 per person are available. Travel duration is 7h 30m
Greyhound US	11h 50m	11:35 PM	Chicago	Downtown Bus Station	12:25 PM	Windsor, ON	International Transit Terminal	Economy	$39	A Bus from Greyhound US goes from Downtown Bus Station, Chicago (USA) at 9/12/2026 11:35:00 PM to International Transit Terminal, Windsor, ON (Canada) arriving at 9/13/2026 12:25:00 PM. 50 Economy ticket for $39 per person are available. Travel duration is 11h 50m
Greyhound US	9h 25m	6:30 AM	Chicago	Downtown Bus Station	4:55 PM	Windsor, ON	International Transit Terminal	Economy	$40	A Bus from Greyhound US goes from Downtown Bus Station, Chicago (USA) at 9/12/2026 6:30:00 AM to International Transit Terminal, Windsor, ON (Canada) arriving at 9/12/2026 4:55:00 PM. 50 Economy ticket for $40 per person are available. Travel duration is 9h 25m
FlixBus	8h 45m	9:55 AM	Chicago	95th Red Line Station	7:40 PM	Windsor, ON	International Transit Terminal	Economy	$60	A Bus from FlixBus goes from 95th Red Line Station, Chicago (USA) at 9/12/2026 9:55:00 AM to International Transit Terminal, Windsor, ON (Canada) arriving at 9/12/2026 7:40:00 PM. 50 Economy ticket for $60 per person are available. Travel duration is 8h 45m

Cheapest bus trips Sunday
BertCompanyCountOneCompanyName	Duration	Departure time	From	Departure	Arrival time	To	Destination	Seat classes	Price
FlixBus	9h 10m	9:30 AM	Chicago	Downtown Bus Station	7:40 PM	Windsor, ON	International Transit Terminal	Economy	$46	A Bus from FlixBus goes from Downtown Bus Station, Chicago (USA) at 9/13/2026 9:30:00 AM to International Transit Terminal, Windsor, ON (Canada) arriving at 9/13/2026 7:40:00 PM. 50 Economy ticket for $46 per person are available. Travel duration is 9h 10m
Greyhound US	9h 25m	6:30 AM	Chicago	Downtown Bus Station	4:55 PM	Windsor, ON	International Transit Terminal	Economy	$46	A Bus from Greyhound US goes from Downtown Bus Station, Chicago (USA) at 9/13/2026 6:30:00 AM to International Transit Terminal, Windsor, ON (Canada) arriving at 9/13/2026 4:55:00 PM. 50 Economy ticket for $46 per person are available. Travel duration is 9h 25m
Greyhound US	7h 30m	3:55 PM	Chicago	Downtown Bus Station	12:25 AM	Windsor, ON	International Transit Terminal	Economy	$46	A Bus from Greyhound US goes from Downtown Bus Station, Chicago (USA) at 9/13/2026 3:55:00 PM to International Transit Terminal, Windsor, ON (Canada) arriving at 9/14/2026 12:25:00 AM. 50 Economy ticket for $46 per person are available. Travel duration is 7h 30m
Greyhound US	11h 50m	11:35 PM	Chicago	Downtown Bus Station	12:25 PM	Windsor, ON	International Transit Terminal	Economy	$46	A Bus from Greyhound US goes from Downtown Bus Station, Chicago (USA) at 9/13/2026 11:35:00 PM to International Transit Terminal, Windsor, ON (Canada) arriving at 9/14/2026 12:25:00 PM. 50 Economy ticket for $46 per person are available. Travel duration is 11h 50m
FlixBus	10h 40m	5:15 AM	Chicago	95th Red Line Station	4:55 PM	Windsor, ON	International Transit Terminal	Economy	$54	A Bus from FlixBus goes from 95th Red Line Station, Chicago (USA) at 9/13/2026 5:15:00 AM to International Transit Terminal, Windsor, ON (Canada) arriving at 9/13/2026 4:55:00 PM. 50 Economy ticket for $54 per person are available. Travel duration is 10h 40m

Best Price Offer: The price for the cheapest bus from Chicago to Windsor, ON is $34 on 9/17/2026. Flexible travelers save on ticket prices.

Frequency of bus connections between Chicago and Windsor, ON

See here how frequent the connections between Chicago and Windsor, ON are, during different times and days of the week.

Sunday is the busiest day, with more than 16 daily buses from Chicago to Windsor, ON. Friday has instead the fewest connections, with only 14 daily coaches between Chicago and Windsor, ON.

The busiest time of the day is the Morning, with 20 buses from Chicago to Windsor, ON, while Evening sees the fewest connections between Chicago and Windsor, ON, with 6 offers.

Facts about the bus from Chicago to Windsor, ON

Compare all providers like Greyhound US and FlixBus that travel 15 times every day by bus from Chicago to Windsor, ON in one click! Book your bus ticket from Chicago to Windsor, ON starting from $34!

Cheapest Bus	$34
Fastest Bus	8h 30m
Earliest Bus	5:15 AM
Latest Bus	11:35 PM
Daily Bus Routes	15 Ø
Distance	237.9 miles
Bus Companies	Greyhound US and FlixBus

Cheapest bus connections from Chicago to Windsor, ON

Every day, 15 buses from 2 bus companies leave Chicago for Windsor, ON: in the table below, you will find the cheapest prices for a bus ticket for this route, starting from 09/07/2026 and for the following days.

Sunday

Monday

Tuesday

Wednesday

Thursday

Friday

Saturday

Sunday 09/06

Monday 09/07

$51

Tuesday 09/08

$45

Wednesday 09/09

$36

Thursday 09/10

Friday 09/11

$42

Saturday 09/12

$39

Sunday 09/13

$46

Monday 09/14

$39

Tuesday 09/15

$35

Wednesday 09/16

$36

Thursday 09/17

$34

Friday 09/18

Saturday 09/19

Sunday 09/20

Monday 09/21

$41

Tuesday 09/22

Wednesday 09/23

Thursday 09/24

Friday 09/25

Saturday 09/26

Sunday 09/27

Monday 09/28

Tuesday 09/29

Wednesday 09/30

Thursday 10/01

Friday 10/02

Saturday 10/03

The cheapest time to travel from Chicago to Windsor, ON

See here on which day and which time of the day you can find the cheapest bus ticket from Chicago to Windsor, ON, for the next 30 days.

With a price starting from $39, Saturday is the cheapest day for a bus from Chicago to Windsor, ON. Sunday instead is the most expensive day with prices starting from $46.

Night is the cheapest day time for bus tickets from Chicago to Windsor, ON, with $34. Morning is the most expensive time of the day with prices starting from $39.

How to save money travelling from Chicago to Windsor, ON

Travel can be expensive, but it doesn't need to be! Do you want to avoid paying a terrible price for your trip? Then follow these quick steps to save money:

Book the ticket from Chicago to Windsor, ON in advance! The earlier you book, the cheaper usually the price is. Also, you will be sure to have a place on the bus from Chicago to Windsor, ON, compared instead if you buy it at the last moment, or directly at the station.

If you can, avoid travelling at peak times. Instead of weekend, try travelling during the week. Travelling in the evening or at night it’s also cheaper, and later buses from Chicago to Windsor, ON are also emptier.

All bus stations and stops in Chicago and Windsor, ON

In the map below, you can see where to find all bus stations in Chicago and Windsor, ON.

95th Red Line Station

W. 95th St 14

Downtown Bus Station

West Harrison Street 630-670

Union Station

S Canal St 225

Cumberland CTA

N Cumberland Ave 5800

Canal & Van Buren

S Canal St 310-320

International Transit Terminal

Chatham Street West 300

University

University Ave W

Service and Comfort on the bus from Chicago to Windsor, ON

Want to know which seat classes are available on the buses from Chicago to Windsor, ON? Or which bus companies serve the route Chicago to Windsor, ON? Below you will find answers to your questions.

FAQs about the Chicago to Windsor, ON bus

How much does a Chicago Windsor, ON bus trip cost?

This depends on, among other things, the day and time of travel. The cheapest trip is available from $34 and takes 10h 10m to reach Windsor, ON. Compare offers to save money!

How much could I save by comparing buses from Chicago to Windsor, ON?

This route is offered by 2 companies with a range of ticket prices between $34 and $68. Thus, we recommend booking your ticket as early as possible to make sure you get the cheapest bus ticket to Windsor, ON.

On average, how many connections are available from Chicago to Windsor, ON each day?

Every day, the Chicago to Windsor, ON bus route is served by approximately 15 connections. With our search, you can compare bus times to find the perfect trip.

How long does a bus journey from Chicago to Windsor, ON take?

The fastest bus from Chicago to Windsor, ON is offered by Greyhound US and takes 8h 30m. Bus tickets for this connection cost $43. In this context, bear in mind that the journey can take longer due to traffic.

What time is the first bus from Chicago to Windsor, ON?

The earliest bus arriving in Windsor, ON from Chicago starts at 5:15 AM. However, information regarding departure times may differ on weekends and holidays. Simply use our search to find exact times for your planned travel date.

What time is the last bus from Chicago to Windsor, ON?

The latest bus trip departing from Chicago for Windsor, ON starts at 11:35 PM. Please note that departure times may differ on weekends and holidays. So just use our search to find the exact times for your planned travel date.

Which bus companies operate the Chicago Windsor, ON route?

When traveling by bus from Chicago to Windsor, ON, passengers can travel with Greyhound US and FlixBus. With our search, you can compare all available bus tickets to book the one that works for you.

Is there a direct bus between Chicago and Windsor, ON?

You can check all the direct connections between Chicago and Windsor, ON by using our search and looking at the Changes section in our filters. These are some of the companies which offer a direct bus: Greyhound US and FlixBus.

What can I take with me on the Chicago to Windsor, ON bus route?

Depending on which provider you travel with, what you're allowed to bring with you can vary. Generally, you can take a suitcase and hand luggage with you on the Chicago Windsor, ON bus route free of charge. Simply use our search to find a bus that is best suited to your needs for your planned travel date.

What equipment is available for the Chicago Windsor, ON bus route?

The equipment on board differs depending on the provider. However, many long-distance buses have WiFi so you can tell your friends your exact location during the journey. To make traveling even more pleasant, air conditioning systems provide ventilation. It is best to use our search to get precise information about the equipment of the bus from Chicago to Windsor, ON on your planned travel date.

Available seat classes which are offered on the bus route Chicago to Windsor, ON

Economy

The cheapest option available for your ticket, it usually comes with reclinable seats and AC.

More bus routes to Chicago and to Windsor, ON

Here’s an overview of the most popular bus routes to Chicago and to Windsor, ON. Simply click on the connection of your choice, and you will find all the details about your bus route!