Which bus from Chicago to Windsor, ON is the cheapest?

Compare all bus companies and find the best price: Bus tickets from $35
Search for your destination Millions of deals worldwide
Compare results Save up to 70%
Find the right bus for you Easy and transparent

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
$42
tomorrow
$43
Sunday
Monday
$43
Tuesday
Wednesday
Thursday
$36

Cheapest bus trips today

Mode of Transport BertCompanyCountOneCompanyName Duration Departure time From Departure Arrival time To Destination Logo Seat classes Price
Greyhound US 7h 30m 3:55 PM Chicago Downtown Bus Station 12:25 AM Windsor, ON International Transit Terminal  Economy $42
Greyhound US 11h 50m 11:35 PM Chicago Downtown Bus Station 12:25 PM Windsor, ON International Transit Terminal  Economy $42
Greyhound US 9h 25m 6:30 AM Chicago Downtown Bus Station 4:55 PM Windsor, ON International Transit Terminal  Economy $48
FlixBus 10h 30m 5:25 AM Chicago 95th Red Line Station 4:55 PM Windsor, ON International Transit Terminal  Economy $52
FlixBus 16h 0m 7:25 PM Chicago 95th Red Line Station 12:25 PM Windsor, ON International Transit Terminal  Economy $52

Cheapest bus trips tomorrow

Mode of Transport BertCompanyCountOneCompanyName Duration Departure time From Departure Arrival time To Destination Logo Seat classes Price
FlixBus 9h 10m 9:30 AM Chicago Downtown Bus Station 7:40 PM Windsor, ON International Transit Terminal  Economy $43
Greyhound US 9h 25m 6:30 AM Chicago Downtown Bus Station 4:55 PM Windsor, ON International Transit Terminal  Economy $43
Greyhound US 7h 30m 3:55 PM Chicago Downtown Bus Station 12:25 AM Windsor, ON International Transit Terminal  Economy $43
Greyhound US 11h 50m 11:35 PM Chicago Downtown Bus Station 12:25 PM Windsor, ON International Transit Terminal  Economy $43
FlixBus 10h 30m 5:25 AM Chicago 95th Red Line Station 4:55 PM Windsor, ON International Transit Terminal  Economy $52

Cheapest bus trips Monday

Mode of Transport BertCompanyCountOneCompanyName Duration Departure time From Departure Arrival time To Destination Logo Seat classes Price
FlixBus 9h 10m 9:30 AM Chicago Downtown Bus Station 7:40 PM Windsor, ON International Transit Terminal  Economy $43
Greyhound US 9h 25m 6:30 AM Chicago Downtown Bus Station 4:55 PM Windsor, ON International Transit Terminal  Economy $43
Greyhound US 7h 30m 3:55 PM Chicago Downtown Bus Station 12:25 AM Windsor, ON International Transit Terminal  Economy $43
Greyhound US 11h 50m 11:35 PM Chicago Downtown Bus Station 12:25 PM Windsor, ON International Transit Terminal  Economy $43
FlixBus 10h 30m 5:25 AM Chicago 95th Red Line Station 4:55 PM Windsor, ON International Transit Terminal  Economy $52
  • Did you know that if you travel from Detroit to Chicago via Windsor, ON, you can save more than $32? You will find the corresponding connections below.
    • FlixBus
      Save more than 74%
      0h 55m
      0 mi
      11:30 PM
      Detroit
      Central Bus Station
      12:25 AM
      Windsor, ON
      International Transit Terminal
      237 mi
      Chicago
      FlixBus
      Economy
      $11

Cheapest bus trips Thursday

Mode of Transport BertCompanyCountOneCompanyName Duration Departure time From Departure Arrival time To Destination Logo Seat classes Price
Greyhound US 9h 25m 6:30 AM Chicago Downtown Bus Station 4:55 PM Windsor, ON International Transit Terminal  Economy $36
Greyhound US 7h 30m 3:55 PM Chicago Downtown Bus Station 12:25 AM Windsor, ON International Transit Terminal  Economy $36
Greyhound US 11h 50m 11:35 PM Chicago Downtown Bus Station 12:25 PM Windsor, ON International Transit Terminal  Economy $36
FlixBus 10h 30m 5:25 AM Chicago 95th Red Line Station 4:55 PM Windsor, ON International Transit Terminal  Economy $53
FlixBus 16h 0m 7:25 PM Chicago 95th Red Line Station 12:25 PM Windsor, ON International Transit Terminal  Economy $53

Best Price Offer: The price for the cheapest bus from Chicago to Windsor, ON is $35 on 8/4/2026. 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.
Saturday is the busiest day, with more than 18 daily buses from Chicago to Windsor, ON. Monday has instead the fewest connections, with only 9 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 Night sees the fewest connections between Chicago and Windsor, ON, with 7 offers.

Facts about the bus from Chicago to Windsor, ON

Compare all providers like Greyhound US and FlixBus that travel 13 times every day by bus from Chicago to Windsor, ON in one click! Book your bus ticket from Chicago to Windsor, ON starting from $35!

Cheapest Bus $35
Fastest Bus 8h 30m
Earliest Bus 5:25 AM
Latest Bus 11:35 PM
Daily Bus Routes 13 Ø
Distance 237.9 miles
Bus Companies Greyhound US and FlixBus

Cheapest bus connections from Chicago to Windsor, ON

Every day, 13 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 07/24/2026 and for the following days.

Sunday
Monday
Tuesday
Wednesday
Thursday
Friday
Saturday
Sunday 07/19
Monday 07/20
Tuesday 07/21
Wednesday 07/22
Thursday 07/23
Friday 07/24
$42
Saturday 07/25
$43
Sunday 07/26
Monday 07/27
$43
Tuesday 07/28
Wednesday 07/29
Thursday 07/30
$36
Friday 07/31
$38
Saturday 08/01
$45
Sunday 08/02
$48
Monday 08/03
$37
Tuesday 08/04
$35
Wednesday 08/05
$43
Thursday 08/06
$39
Friday 08/07
$48
Saturday 08/08
$38
Sunday 08/09
$43
Monday 08/10
$43
Tuesday 08/11
$42
Wednesday 08/12
$43
Thursday 08/13
Friday 08/14
Saturday 08/15

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 $36, Thursday is the cheapest day for a bus from Chicago to Windsor, ON. Saturday instead is the most expensive day with prices starting from $38.
Night is the cheapest day time for bus tickets from Chicago to Windsor, ON, with $35. Afternoon is the most expensive time of the day with prices starting from $36.

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.

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 $35 and takes 10h 25m 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 $35 and $75. 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 13 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 $46. 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 5:25 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
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!
Bus to Chicago from South Bend, IN Bus to Chicago from South Bend, IN
Bus to Chicago from Davenport, IA Bus to Chicago from Davenport, IA
From El Cajon, CA to Chicago bus From El Cajon, CA to Chicago bus
From Tucson, AZ to Chicago bus From Tucson, AZ to Chicago bus
New Haven, CT to Windsor, ON bus New Haven, CT to Windsor, ON bus
Bus to Windsor, ON from Waco, TX Bus to Windsor, ON from Waco, TX
Buses Saint Catharines, ON - Windsor, ON Buses Saint Catharines, ON - Windsor, ON
Bus from Omaha to Windsor, ON Bus from Omaha to Windsor, ON
Popular Airport Shuttles to Chicago and to Windsor, ON
CheckMyBus › Buses in USA › Bus to Chicago › Bus to Windsor, ON

The CheckMyBus App

Free Download

App Store
CheckMyBus App
Close
GPDR CheckMyBus shield

We value your privacy!

To

show

you

the

best

bus

offers,

we

and

our

partners

use

technical,

analytical,

and

marketing

cookies

to

personalize

the

ads.

We

remember

your

anonymized

details

to

provide

a

personalized

experience.