Bus Windsor, ON to Chicago: Compare prices and save money

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

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

today

$52

tomorrow

Wednesday

Thursday

Friday

Saturday

Sunday

Cheapest bus trips today
BertCompanyCountOneCompanyName	Duration	Departure time	From	Departure	Arrival time	To	Destination	Seat classes	Price
FlixBus	10h 25m	2:10 PM	Windsor, ON	International Transit Terminal	11:35 PM	Chicago	95th Red Line Station	Economy	$52	A Bus from FlixBus goes from International Transit Terminal, Windsor, ON (Canada) at 9/7/2026 2:10:00 PM to 95th Red Line Station, Chicago (USA) arriving at 9/7/2026 11:35:00 PM. 50 Economy ticket for $52 per person are available. Travel duration is 10h 25m
FlixBus	14h 15m	8:35 PM	Windsor, ON	International Transit Terminal	9:50 AM	Chicago	95th Red Line Station	Economy	$52	A Bus from FlixBus goes from International Transit Terminal, Windsor, ON (Canada) at 9/7/2026 8:35:00 PM to 95th Red Line Station, Chicago (USA) arriving at 9/8/2026 9:50:00 AM. 50 Economy ticket for $52 per person are available. Travel duration is 14h 15m
FlixBus	10h 5m	8:30 AM	Windsor, ON	International Transit Terminal	5:35 PM	Chicago	Downtown Bus Station	Economy	$53	A Bus from FlixBus goes from International Transit Terminal, Windsor, ON (Canada) at 9/7/2026 8:30:00 AM to Downtown Bus Station, Chicago (USA) arriving at 9/7/2026 5:35:00 PM. 50 Economy ticket for $53 per person are available. Travel duration is 10h 5m
FlixBus	8h 15m	2:10 PM	Windsor, ON	International Transit Terminal	9:25 PM	Chicago	Downtown Bus Station	Economy	$53	A Bus from FlixBus goes from International Transit Terminal, Windsor, ON (Canada) at 9/7/2026 2:10:00 PM to Downtown Bus Station, Chicago (USA) arriving at 9/7/2026 9:25:00 PM. 50 Economy ticket for $53 per person are available. Travel duration is 8h 15m
FlixBus	9h 50m	8:35 PM	Windsor, ON	International Transit Terminal	5:25 AM	Chicago	Downtown Bus Station	Economy	$53	A Bus from FlixBus goes from International Transit Terminal, Windsor, ON (Canada) at 9/7/2026 8:35:00 PM to Downtown Bus Station, Chicago (USA) arriving at 9/8/2026 5:25:00 AM. 50 Economy ticket for $53 per person are available. Travel duration is 9h 50m

Did you know that if you travel from Windsor, ON to Chicago via Detroit, you can save more than $8? You will find the corresponding connections below.
- Save more than 15%
  
  6h 5m
  
  Windsor, ON
  
  2 mi
  
  4:20 PM
  
  Detroit
  Central Bus Station
  
  9:25 PM
  
  Chicago
  Downtown Bus Station
  
  0 mi
  
  Economy
  
  $44
  
  A Bus from goes from Central Bus Station, Detroit (USA) at 9/7/2026 4:20:00 PM to Downtown Bus Station, Chicago (USA) arriving at 9/7/2026 9:25:00 PM. 50 Economy ticket for $44 per person are available. Travel duration is 6h 5m

Test cheapest views

The cheapest bus for the 9/19/2026 costs just $38, from FlixBus

Facts about the bus from Windsor, ON to Chicago

Compare all providers like FlixBus that travel 12 times every day by bus from Windsor, ON to Chicago in one click! Book your bus ticket from Windsor, ON to Chicago starting from $38!

Cheapest Bus	$38
Fastest Bus	7h 15m
Earliest Bus	8:30 AM
Latest Bus	8:35 PM
Daily Bus Routes	12 Ø
Distance	237.9 miles
Bus Companies	FlixBus

Cheapest bus connections from Windsor, ON to Chicago

Every day, 12 buses from 1 bus companies leave Windsor, ON for Chicago: 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

$48

Tuesday 09/08

$48

Wednesday 09/09

Thursday 09/10

Friday 09/11

Saturday 09/12

$46

Sunday 09/13

Monday 09/14

$39

Tuesday 09/15

Wednesday 09/16

Thursday 09/17

$40

Friday 09/18

Saturday 09/19

$38

Sunday 09/20

Monday 09/21

$49

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

$46

Friday 10/02

Saturday 10/03

How to save money travelling from Windsor, ON to Chicago

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 Windsor, ON to Chicago 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 Windsor, ON to Chicago, 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 Windsor, ON to Chicago are also emptier.

All bus stations and stops in Windsor, ON and Chicago

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

International Transit Terminal

Chatham Street West 300

University

University Ave W

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

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

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

FAQs about the Windsor, ON to Chicago bus

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

This depends on, among other things, the day and time of travel. The cheapest trip is available from $38 and takes 9h 25m to reach Chicago. Compare offers to save money!

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

This route is offered by 1 companies with a range of ticket prices between $38 and $60. Thus, we recommend booking your ticket as early as possible to make sure you get the cheapest bus ticket to Chicago.

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

Every day, the Windsor, ON to Chicago bus route is served by approximately 12 connections. With our search, you can compare bus times to find the perfect trip.

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

The fastest bus from Windsor, ON to Chicago is offered by FlixBus and takes 7h 15m. Bus tickets for this connection cost $56. In this context, bear in mind that the journey can take longer due to traffic.

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

The earliest bus arriving in Chicago from Windsor, ON starts at 8:30 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 Windsor, ON to Chicago?

The latest bus trip departing from Windsor, ON for Chicago starts at 8:35 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 Windsor, ON Chicago route?

When traveling by bus from Windsor, ON to Chicago, passengers can travel with 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 Windsor, ON and Chicago?

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

What can I take with me on the Windsor, ON to Chicago 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 Windsor, ON Chicago 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 Windsor, ON Chicago 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 Windsor, ON to Chicago on your planned travel date.

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

Economy

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

More bus routes to Windsor, ON and to Chicago

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