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

Compare all bus companies and find the best price: Bus tickets from $39
The Best Deals Save up to 70%
The Most Choices Millions of routes worldwide
Easy and Transparent Compare offers with 1 click

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
$54
tomorrow
$47
Sunday
$50
Monday
$43
Tuesday
$43
Wednesday
$43
Thursday
$48

Cheapest bus trips today

Mode of Transport BertCompanyCountOneCompanyName Duration Departure time From Departure Arrival time To Destination Logo Seat classes Price
FlixBus 10h 10m 5:45 AM Chicago 95th Red Line Station 4:55 PM Windsor, ON International Transit Terminal  Economy $54
Greyhound US 10h 5m 1:20 PM Chicago 95th Red Line Station 12:25 AM Windsor, ON International Transit Terminal  Economy $54
FlixBus 16h 0m 7:25 PM Chicago 95th Red Line Station 12:25 PM Windsor, ON International Transit Terminal  Economy $55
Greyhound US 8h 55m 7:00 AM Chicago Downtown Bus Station 4:55 PM Windsor, ON International Transit Terminal  Economy $55
Greyhound US 7h 30m 3:55 PM Chicago Downtown Bus Station 12:25 AM Windsor, ON International Transit Terminal  Economy $55
  • Did you know that if you travel from Detroit to Chicago via Windsor, ON, you can save more than $41? You will find the corresponding connections below.
    • FlixBus
      Save more than 76%
      0h 40m
      0 mi
      11:45 AM
      Detroit
      Central Bus Station
      12:25 PM
      Windsor, ON
      International Transit Terminal
      237 mi
      Chicago
      FlixBus
      Economy
      $13
  • Did you know that if you travel from Chicago to Windsor, ON via Detroit, you can save more than $9? You can find the corresponding connections below.
    • Greyhound US
      7h 30m
      0
      3:55 PM
      Chicago
      Downtown Bus Station
      11:00 PM
      Detroit
      Central Bus Station
      0
      Greyhound US
      Economy
      $36
      • Waiting Time 0h 30m
    • FlixBus
      0h 55m
      0
      11:30 PM
      Detroit
      Central Bus Station
      12:25 AM
      Windsor, ON
      International Transit Terminal
      0
      FlixBus
      Economy
      $9
    Travel Time is 1h 0m shorter, and you will save $9

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 $47
Greyhound US 8h 55m 7:00 AM Chicago Downtown Bus Station 4:55 PM Windsor, ON International Transit Terminal  Economy $47
Greyhound US 7h 30m 3:55 PM Chicago Downtown Bus Station 12:25 AM Windsor, ON International Transit Terminal  Economy $47
Greyhound US 11h 50m 11:35 PM Chicago Downtown Bus Station 12:25 PM Windsor, ON International Transit Terminal  Economy $47
FlixBus 10h 10m 5:45 AM Chicago 95th Red Line Station 4:55 PM Windsor, ON International Transit Terminal  Economy $54
  • Did you know that if you travel from Detroit to Chicago via Windsor, ON, you can save more than $38? You will find the corresponding connections below.
    • FlixBus
      Save more than 81%
      0h 55m
      0 mi
      11:30 PM
      Detroit
      Central Bus Station
      12:25 AM
      Windsor, ON
      International Transit Terminal
      237 mi
      Chicago
      FlixBus
      Economy
      $9

Cheapest bus trips Sunday

Mode of Transport BertCompanyCountOneCompanyName Duration Departure time From Departure Arrival time To Destination Logo Seat classes Price
Greyhound US 8h 55m 7:00 AM Chicago Downtown Bus Station 4:55 PM Windsor, ON International Transit Terminal  Economy $50
FlixBus 9h 10m 9:30 AM Chicago Downtown Bus Station 7:40 PM Windsor, ON International Transit Terminal  Economy $51
Greyhound US 7h 30m 3:55 PM Chicago Downtown Bus Station 12:25 AM Windsor, ON International Transit Terminal  Economy $51
Greyhound US 11h 50m 11:35 PM Chicago Downtown Bus Station 12:25 PM Windsor, ON International Transit Terminal  Economy $51
FlixBus 10h 10m 5:45 AM Chicago 95th Red Line Station 4:55 PM Windsor, ON International Transit Terminal  Economy $56
  • Did you know that if you travel from Detroit to Chicago via Windsor, ON, you can save more than $44? You will find the corresponding connections below.
    • Save more than 88%
      0h 55m
      0 mi
      11:30 PM
      Detroit
      Central Bus Station
      12:25 AM
      Windsor, ON
      International Transit Terminal
      237 mi
      Chicago
      Economy
      $6
  • Did you know that if you travel from Chicago to Windsor, ON via Detroit, you can save more than $5? You can find the corresponding connections below.
    • Greyhound US
      7h 30m
      0
      3:55 PM
      Chicago
      Downtown Bus Station
      11:00 PM
      Detroit
      Central Bus Station
      0
      Greyhound US
      Economy
      $36
      • Waiting Time 0h 30m
    • FlixBus
      0h 55m
      0
      11:30 PM
      Detroit
      Central Bus Station
      12:25 AM
      Windsor, ON
      International Transit Terminal
      0
      FlixBus
      Economy
      $9
    Travel Time is 1h 0m shorter, and you will save $5

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 8h 55m 7:00 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 10m 5:45 AM Chicago 95th Red Line Station 4:55 PM Windsor, ON International Transit Terminal  Economy $54

Cheapest bus trips Tuesday

Mode of Transport BertCompanyCountOneCompanyName Duration Departure time From Departure Arrival time To Destination Logo Seat classes Price
Greyhound US 8h 55m 7:00 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 10m 5:45 AM Chicago 95th Red Line Station 4:55 PM Windsor, ON International Transit Terminal  Economy $54
FlixBus 18h 20m 5:05 PM Chicago 95th Red Line Station 12:25 PM Windsor, ON International Transit Terminal  Economy $54

Cheapest bus trips Wednesday

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 $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
FlixBus 16h 0m 7:25 PM Chicago 95th Red Line Station 12:25 PM Windsor, ON International Transit Terminal  Economy $53

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 $48
Greyhound US 11h 50m 11:35 PM Chicago Downtown Bus Station 12:25 PM Windsor, ON International Transit Terminal  Economy $49
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
  • Did you know that if you travel from Chicago to Windsor, ON via Detroit, you can save more than $7? You can find the corresponding connections below.
    • Greyhound US
      7h 30m
      0
      3:55 PM
      Chicago
      Downtown Bus Station
      11:00 PM
      Detroit
      Central Bus Station
      0
      Greyhound US
      Economy
      $36
      • Waiting Time 0h 30m
    • FlixBus
      0h 55m
      0
      11:30 PM
      Detroit
      Central Bus Station
      12:25 AM
      Windsor, ON
      International Transit Terminal
      0
      FlixBus
      Economy
      $5
    Travel Time is 2h 55m shorter, and you will save $7

Best Price Offer: The price for the cheapest bus from Chicago to Windsor, ON is $39 on 6/25/2026. 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 18 daily buses from Chicago to Windsor, ON. Wednesday has instead the fewest connections, with only 8 daily coaches between Chicago and Windsor, ON.
The busiest time of the day is the Morning, with 36 buses from Chicago to Windsor, ON, while Night sees the fewest connections between Chicago and Windsor, ON, with 14 offers.

Facts about the bus from Chicago to Windsor, ON

Compare all providers like Greyhound US and FlixBus that travel 14 times every day by bus from Chicago to Windsor, ON in one click! Book your bus ticket from Chicago to Windsor, ON starting from $39!

Cheapest Bus $39
Fastest Bus 8h 30m
Earliest Bus 5:45 AM
Latest Bus 11:35 PM
Daily Bus Routes 14 Ø
Distance 237.9 miles
Bus Companies Greyhound US and FlixBus

Cheapest bus connections from Chicago to Windsor, ON

Every day, 14 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 06/12/2026 and for the following days.

Sunday
Monday
Tuesday
Wednesday
Thursday
Friday
Saturday
Sunday 06/07
Monday 06/08
Tuesday 06/09
Wednesday 06/10
Thursday 06/11
Friday 06/12
$54
Saturday 06/13
$47
Sunday 06/14
$50
Monday 06/15
$43
Tuesday 06/16
$43
Wednesday 06/17
$43
Thursday 06/18
$48
Friday 06/19
$48
Saturday 06/20
$50
Sunday 06/21
$65
Monday 06/22
$45
Tuesday 06/23
$41
Wednesday 06/24
$40
Thursday 06/25
$39
Friday 06/26
$47
Saturday 06/27
$50
Sunday 06/28
$54
Monday 06/29
$48
Tuesday 06/30
$46
Wednesday 07/01
$52
Thursday 07/02
Friday 07/03
$53
Saturday 07/04

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, Thursday is the cheapest day for a bus from Chicago to Windsor, ON. Sunday instead is the most expensive day with prices starting from $50.
Night is the cheapest day time for bus tickets from Chicago to Windsor, ON, with $39. Morning is the most expensive time of the day with prices starting from $43.

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.

Beloved bus companies from Chicago to Windsor, ON

These are the most booked bus companies between Chicago to Windsor, ON from our users.

FlixBus from Chicago to Windsor, ON

FlixBus

Here you will find the key facts about the FlixBus bus route Chicago to Windsor, ON:

Cheapest Price $43
Fastest Bus 9h 45m
Earliest Bus 5:45 AM
Last Bus 7:25 PM
Daily Connections 5 Ø
Found on 6/11/2026

Greyhound US from Chicago to Windsor, ON

Greyhound US

Here you will find the key facts about the Greyhound US bus route Chicago to Windsor, ON:

Cheapest Price $43
Fastest Bus 8h 30m
Earliest Bus 7:00 AM
Last Bus 11:35 PM
Daily Connections 8 Ø
Found on 6/11/2026

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 $39 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 $39 and $84. 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 14 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 $60. 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 5:45 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.

How does CheckMyBus find the best bus deals from Chicago to Windsor, ON?

CheckMyBus collaborates directly with companies around the world to provide you with the best options when searching for a trip. We retrieve their first-hand data to show you real-time prices, schedules, and seat availability for 14 daily trips between Chicago and Windsor, ON. With the most up-to-date information from verified sources, you can fairly compare all available options and choose the trip that suits you best.

How does CheckMyBus technology work for trips from Chicago to Windsor, ON?

Prices and availability for 14 trips between Chicago and Windsor, ON change constantly. To provide you with the most up-to-date information, we connect directly with bus operators, Online Travel Agencies (OTAs), and Global Distribution Systems (GDS) via real-time interfaces (APIs). The data collected from these sources undergoes strict quality checks, is processed within our infrastructure, and is then presented to you on our search results pages. Visit our About Us page to learn more.

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!
Buses from Mission Palmview, TX to Chicago Buses from Mission Palmview, TX to Chicago
Buses to Chicago from Plainview, TX Buses to Chicago from Plainview, TX
Buses Barstow, CA - Chicago Buses Barstow, CA - Chicago
Bus to Chicago from Omaha Bus to Chicago from Omaha
Bus to Windsor, ON from Huntsville, AL Bus to Windsor, ON from Huntsville, AL
Buses Richmond, VA - Windsor, ON Buses Richmond, VA - Windsor, ON
Buses Glendale, AZ - Windsor, ON Buses Glendale, AZ - Windsor, ON
Buses from Indianapolis to Windsor, ON Buses from Indianapolis 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.