Bus from Chicago to Windsor, ON from $44

Compare 2 companies and find the best price with CheckMyBus
1
Search accommodation with Booking.com
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
from $47
tomorrow
Friday
from $57
Saturday
from $64
Sunday
from $61
Monday
from $61
Tuesday
from $44

Cheapest bus trips today

Prices are for one way and one person
  • Greyhound US
    10h 0m
    0
    6:55 AM
    Chicago
    Downtown Bus Station
    4:55 PM
    Windsor, ON
    International Transit Terminal
    0
    Greyhound US
    Economy
    $47
  • Greyhound US
    9h 0m
    0
    10:10 PM
    Chicago
    Downtown Bus Station
    7:10 AM
    Windsor, ON
    International Transit Terminal
    0
    Greyhound US
    Economy
    $47
  • 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.
    • Busbud
      8h 30m
      0
      3:55 PM
      Chicago
      Downtown Bus Station
      11:00 PM
      Detroit
      Central Bus Station
      0
      Busbud
      Economy
      $32
      • Waiting Time 0h 45m
    • Busbud
      0h 40m
      0
      11:45 PM
      Detroit
      Central Bus Station
      12:25 AM
      Windsor, ON
      International Transit Terminal
      0
      Busbud
      Economy
      $10
    Travel Time is 0h 30m shorter, and you will save $5

Cheapest bus trips Friday

Prices are for one way and one person
  • Greyhound US
    10h 0m
    0
    6:55 AM
    Chicago
    Downtown Bus Station
    4:55 PM
    Windsor, ON
    International Transit Terminal
    0
    Greyhound US
    Economy
    $57
  • Greyhound US
    8h 15m
    0
    3:55 PM
    Chicago
    Downtown Bus Station
    12:10 AM
    Windsor, ON
    International Transit Terminal
    0
    Greyhound US
    Economy
    $57
  • Greyhound US
    9h 0m
    0
    10:10 PM
    Chicago
    Downtown Bus Station
    7:10 AM
    Windsor, ON
    International Transit Terminal
    0
    Greyhound US
    Economy
    $57
  • FlixBus
    11h 10m
    0
    5:45 AM
    Chicago
    95th Red Line Station
    4:55 PM
    Windsor, ON
    International Transit Terminal
    0
    FlixBus
    Economy
    $67
  • Did you know that if you travel from Chicago to Windsor, ON via Detroit, you can save more than $15? You can find the corresponding connections below.
    • Busbud
      8h 30m
      0
      3:55 PM
      Chicago
      Downtown Bus Station
      11:00 PM
      Detroit
      Central Bus Station
      0
      Busbud
      Economy
      $32
      • Waiting Time 0h 45m
    • Busbud
      0h 40m
      0
      11:45 PM
      Detroit
      Central Bus Station
      12:25 AM
      Windsor, ON
      International Transit Terminal
      0
      Busbud
      Economy
      $10
    Travel time is 0h 15m longer, but you will save $15

Cheapest bus trips Saturday

Prices are for one way and one person
  • Greyhound US
    14h 10m
    0
    10:00 AM
    Chicago
    Union Station
    12:10 AM
    Windsor, ON
    International Transit Terminal
    0
    Greyhound US
    Economy
    $64
  • Greyhound US
    10h 0m
    0
    6:55 AM
    Chicago
    Downtown Bus Station
    4:55 PM
    Windsor, ON
    International Transit Terminal
    0
    Greyhound US
    Economy
    $65
  • Greyhound US
    8h 15m
    0
    3:55 PM
    Chicago
    Downtown Bus Station
    12:10 AM
    Windsor, ON
    International Transit Terminal
    0
    Greyhound US
    Economy
    $65
  • FlixBus
    11h 10m
    0
    5:45 AM
    Chicago
    95th Red Line Station
    4:55 PM
    Windsor, ON
    International Transit Terminal
    0
    FlixBus
    Economy
    $67
  • Did you know that if you travel from Detroit to Chicago via Windsor, ON, you can save more than $51? You will find the corresponding connections below.
    • FlixBus
      Save more than 80%
      0h 40m
      0 mi
      6:30 AM
      Detroit
      Central Bus Station
      7:10 AM
      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 $22? You can find the corresponding connections below.
    • Busbud
      8h 30m
      0
      3:55 PM
      Chicago
      Downtown Bus Station
      11:00 PM
      Detroit
      Central Bus Station
      0
      Busbud
      Economy
      $32
      • Waiting Time 0h 45m
    • Busbud
      0h 40m
      0
      11:45 PM
      Detroit
      Central Bus Station
      12:25 AM
      Windsor, ON
      International Transit Terminal
      0
      Busbud
      Economy
      $10
    Travel time is 0h 15m longer, but you will save $22

Cheapest bus trips Sunday

Prices are for one way and one person
  • Greyhound US
    10h 0m
    0
    6:55 AM
    Chicago
    Downtown Bus Station
    4:55 PM
    Windsor, ON
    International Transit Terminal
    0
    Greyhound US
    Economy
    $61
  • Greyhound US
    8h 15m
    0
    3:55 PM
    Chicago
    Downtown Bus Station
    12:10 AM
    Windsor, ON
    International Transit Terminal
    0
    Greyhound US
    Economy
    $62
  • Greyhound US
    9h 0m
    0
    10:10 PM
    Chicago
    Downtown Bus Station
    7:10 AM
    Windsor, ON
    International Transit Terminal
    0
    Greyhound US
    Economy
    $62
  • FlixBus
    11h 10m
    0
    5:45 AM
    Chicago
    95th Red Line Station
    4:55 PM
    Windsor, ON
    International Transit Terminal
    0
    FlixBus
    Economy
    $67
  • Did you know that if you travel from Detroit to Chicago via Windsor, ON, you can save more than $47? You will find the corresponding connections below.
    • FlixBus
      Save more than 77%
      0h 40m
      0 mi
      6:30 AM
      Detroit
      Central Bus Station
      7:10 AM
      Windsor, ON
      International Transit Terminal
      237 mi
      Chicago
      FlixBus
      Economy
      $14
  • Did you know that if you travel from Chicago to Windsor, ON via Detroit, you can save more than $19? You can find the corresponding connections below.
    • Busbud
      8h 30m
      0
      3:55 PM
      Chicago
      Downtown Bus Station
      11:00 PM
      Detroit
      Central Bus Station
      0
      Busbud
      Economy
      $32
      • Waiting Time 0h 45m
    • Busbud
      0h 40m
      0
      11:45 PM
      Detroit
      Central Bus Station
      12:25 AM
      Windsor, ON
      International Transit Terminal
      0
      Busbud
      Economy
      $10
    Travel time is 0h 15m longer, but you will save $19

Cheapest bus trips Monday

Prices are for one way and one person
  • Greyhound US
    10h 0m
    0
    6:55 AM
    Chicago
    Downtown Bus Station
    4:55 PM
    Windsor, ON
    International Transit Terminal
    0
    Greyhound US
    Economy
    $61
  • Greyhound US
    8h 15m
    0
    3:55 PM
    Chicago
    Downtown Bus Station
    12:10 AM
    Windsor, ON
    International Transit Terminal
    0
    Greyhound US
    Economy
    $62
  • Greyhound US
    9h 0m
    0
    10:10 PM
    Chicago
    Downtown Bus Station
    7:10 AM
    Windsor, ON
    International Transit Terminal
    0
    Greyhound US
    Economy
    $62
  • FlixBus
    11h 10m
    0
    5:45 AM
    Chicago
    95th Red Line Station
    4:55 PM
    Windsor, ON
    International Transit Terminal
    0
    FlixBus
    Economy
    $67
  • Did you know that if you travel from Detroit to Chicago via Windsor, ON, you can save more than $51? You will find the corresponding connections below.
    • Save more than 84%
      0h 40m
      0 mi
      11:45 PM
      Detroit
      Central Bus Station
      12:25 AM
      Windsor, ON
      International Transit Terminal
      237 mi
      Chicago
      Economy
      $10
  • Did you know that if you travel from Chicago to Windsor, ON via Detroit, you can save more than $19? You can find the corresponding connections below.
    • Busbud
      8h 30m
      0
      3:55 PM
      Chicago
      Downtown Bus Station
      11:00 PM
      Detroit
      Central Bus Station
      0
      Busbud
      Economy
      $32
      • Waiting Time 0h 45m
    • Busbud
      0h 40m
      0
      11:45 PM
      Detroit
      Central Bus Station
      12:25 AM
      Windsor, ON
      International Transit Terminal
      0
      Busbud
      Economy
      $10
    Travel time is 0h 15m longer, but you will save $19

Cheapest bus trips Tuesday

Prices are for one way and one person
  • Greyhound US
    10h 0m
    0
    6:55 AM
    Chicago
    Downtown Bus Station
    4:55 PM
    Windsor, ON
    International Transit Terminal
    0
    Greyhound US
    Economy
    $44
  • Greyhound US
    8h 15m
    0
    3:55 PM
    Chicago
    Downtown Bus Station
    12:10 AM
    Windsor, ON
    International Transit Terminal
    0
    Greyhound US
    Economy
    $44
  • Greyhound US
    9h 0m
    0
    10:10 PM
    Chicago
    Downtown Bus Station
    7:10 AM
    Windsor, ON
    International Transit Terminal
    0
    Greyhound US
    Economy
    $44
  • Greyhound US
    14h 10m
    0
    10:00 AM
    Chicago
    Union Station
    12:10 AM
    Windsor, ON
    International Transit Terminal
    0
    Greyhound US
    Economy
    $50
  • Did you know that if you travel from Detroit to Chicago via Windsor, ON, you can save more than $31? You will find the corresponding connections below.
    • FlixBus
      Save more than 70%
      0h 40m
      0 mi
      6:30 AM
      Detroit
      Central Bus Station
      7:10 AM
      Windsor, ON
      International Transit Terminal
      237 mi
      Chicago
      FlixBus
      Economy
      $13

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 7 daily buses from Chicago to Windsor, ON. Wednesday has instead the fewest connections, with only 2 daily coaches between Chicago and Windsor, ON.
The busiest time of the day is the Morning, with 11 buses from Chicago to Windsor, ON, while Night sees the fewest connections between Chicago and Windsor, ON, with 4 offers.

Facts about the bus from Chicago to Windsor, ON

Compare all providers like Greyhound US and FlixBus that travel 5 times every day by bus from Chicago to Windsor, ON in one click! Book your bus ticket from Chicago to Windsor, ON starting from $44!

Cheapest Bus $44
Fastest Bus 8h 15m
Earliest Bus 6:55 AM
Latest Bus 10:10 PM
Daily Bus Routes 5 Ø
Distance 237.9 miles
Bus Companies Greyhound US and FlixBus

Cheapest bus connections from Chicago to Windsor, ON

Every day, 5 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 04/24/2025 and for the following days.

Sunday
Monday
Tuesday
Wednesday
Thursday
Friday
Saturday
Sunday 04/20
Monday 04/21
Tuesday 04/22
Wednesday 04/23
$47
Thursday 04/24
$42
Friday 04/25
$53
Saturday 04/26
$60
Sunday 04/27
$57
Monday 04/28
$43
Tuesday 04/29
$44
Wednesday 04/30
Thursday 05/01
$43
Friday 05/02
$41
Saturday 05/03
Sunday 05/04
Monday 05/05
Tuesday 05/06
Wednesday 05/07
Thursday 05/08
Friday 05/09
Saturday 05/10
Sunday 05/11
Monday 05/12
Tuesday 05/13
$40
Wednesday 05/14
Thursday 05/15
$34
Friday 05/16
Saturday 05/17

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 $44, Tuesday is the cheapest day for a bus from Chicago to Windsor, ON. Saturday instead is the most expensive day with prices starting from $64.
Afternoon is the cheapest day time for bus tickets from Chicago to Windsor, ON, with $44. Night is the most expensive time of the day with prices starting from $67.

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 $44 and takes 8h 15m 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 $44 and $79. 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 5 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 15m. Bus tickets for this connection cost $57. 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 6:55 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 10:10 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 Dallas - Chicago Bus Dallas - Chicago
Buses Iowa City, IA - Chicago Buses Iowa City, IA - Chicago
Buses from Bloomington, IN to Chicago Buses from Bloomington, IN to Chicago
Bus Cleveland - Chicago Bus Cleveland - Chicago
Buses from Chatham, ON to Windsor, ON Buses from Chatham, ON to Windsor, ON
Buses London, ON to Windsor, ON Buses London, ON to Windsor, ON
Buses Saint Catharines, ON - Windsor, ON Buses Saint Catharines, ON - Windsor, ON
Buses Nashville to Windsor, ON Buses Nashville 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.