Bus from Windsor, ON to Chicago from $38

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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
$47
tomorrow
$44
Thursday
$41
Friday
$50
Saturday
$48
Sunday
$47
Monday
$38

Cheapest bus trips today

Mode of Transport BertCompanyCountOneCompanyName Duration Departure time From Departure Arrival time To Destination Logo Seat classes Price
FlixBus 7h 20m 5:00 AM Windsor, ON International Transit Terminal 11:20 AM Chicago Downtown Bus Station  Economy $47
FlixBus 8h 15m 2:10 PM Windsor, ON International Transit Terminal 9:25 PM Chicago Downtown Bus Station  Economy $47
FlixBus 9h 50m 8:35 PM Windsor, ON International Transit Terminal 5:25 AM Chicago Downtown Bus Station  Economy $47
FlixBus 9h 25m 5:00 AM Windsor, ON International Transit Terminal 1:25 PM Chicago 95th Red Line Station  Economy $49
FlixBus 10h 25m 2:10 PM Windsor, ON International Transit Terminal 11:35 PM Chicago 95th Red Line Station  Economy $54
  • Did you know that if you travel from Windsor, ON to Chicago via Detroit, you can save more than $14? You will find the corresponding connections below.
    • Save more than 30%
      6h 5m
      Windsor, ON
      2 mi
      4:20 PM
      Detroit
      Central Bus Station
      9:25 PM
      Chicago
      Downtown Bus Station
      0 mi
      Economy
      $33

Cheapest bus trips tomorrow

Mode of Transport BertCompanyCountOneCompanyName Duration Departure time From Departure Arrival time To Destination Logo Seat classes Price
FlixBus 13h 35m 5:00 AM Windsor, ON International Transit Terminal 5:35 PM Chicago Downtown Bus Station  Economy $44
FlixBus 8h 15m 2:10 PM Windsor, ON International Transit Terminal 9:25 PM Chicago Downtown Bus Station  Economy $44
FlixBus 9h 50m 8:35 PM Windsor, ON International Transit Terminal 5:25 AM Chicago Downtown Bus Station  Economy $44
FlixBus 10h 25m 2:10 PM Windsor, ON International Transit Terminal 11:35 PM Chicago 95th Red Line Station  Economy $54
FlixBus 14h 15m 8:35 PM Windsor, ON International Transit Terminal 9:50 AM Chicago 95th Red Line Station  Economy $54
  • Did you know that if you travel from Windsor, ON to Chicago via Detroit, you can save more than $-1? You will find the corresponding connections below.
    • 8h 15m
      Windsor, ON
      2 mi
      4:20 PM
      Detroit
      Central Bus Station
      11:35 PM
      Chicago
      95th Red Line Station
      0 mi
      Economy
      $45
  • Did you know that if you travel from Windsor, ON to Chicago via Gary, IN, you can save more than $5? You can find the corresponding connections below.
    • FlixBus
      9h 25m
      0
      5:00 AM
      Windsor, ON
      International Transit Terminal
      12:40 PM
      Gary, IN
      Adam Benjamin JR Metro Center
      0
      FlixBus
      Economy
      $34
      • Waiting Time 0h 5m
    • FlixBus
      0h 40m
      0
      12:45 PM
      Gary, IN
      Adam Benjamin JR Metro Center
      1:25 PM
      Chicago
      Downtown Bus Station
      0
      FlixBus
      Economy
      $5
    Travel time is 2h 10m longer, but you will save $5

Cheapest bus trips Thursday

Mode of Transport BertCompanyCountOneCompanyName Duration Departure time From Departure Arrival time To Destination Logo Seat classes Price
FlixBus 9h 25m 5:00 AM Windsor, ON International Transit Terminal 1:25 PM Chicago Downtown Bus Station  Economy $41
FlixBus 8h 15m 2:10 PM Windsor, ON International Transit Terminal 9:25 PM Chicago Downtown Bus Station  Economy $41
FlixBus 9h 50m 8:35 PM Windsor, ON International Transit Terminal 5:25 AM Chicago Downtown Bus Station  Economy $41
FlixBus 10h 25m 2:10 PM Windsor, ON International Transit Terminal 11:35 PM Chicago 95th Red Line Station  Economy $52
FlixBus 14h 15m 8:35 PM Windsor, ON International Transit Terminal 9:50 AM Chicago 95th Red Line Station  Economy $52

Cheapest bus trips Friday

Mode of Transport BertCompanyCountOneCompanyName Duration Departure time From Departure Arrival time To Destination Logo Seat classes Price
FlixBus 8h 15m 2:10 PM Windsor, ON International Transit Terminal 9:25 PM Chicago Downtown Bus Station  Economy $50
FlixBus 9h 50m 8:35 PM Windsor, ON International Transit Terminal 5:25 AM Chicago Downtown Bus Station  Economy $50
FlixBus 10h 25m 2:10 PM Windsor, ON International Transit Terminal 11:35 PM Chicago 95th Red Line Station  Economy $53
FlixBus 14h 15m 8:35 PM Windsor, ON International Transit Terminal 9:50 AM Chicago 95th Red Line Station  Economy $53
FlixBus 9h 25m 5:00 AM Windsor, ON International Transit Terminal 1:25 PM Chicago 95th Red Line Station  Economy $73
  • Did you know that if you travel from Windsor, ON to Chicago via Detroit, you can save more than $9? You will find the corresponding connections below.
    • Save more than 18%
      6h 5m
      Windsor, ON
      2 mi
      4:20 PM
      Detroit
      Central Bus Station
      9:25 PM
      Chicago
      Downtown Bus Station
      0 mi
      Economy
      $41
  • Did you know that if you travel from Windsor, ON to Chicago via Gary, IN, you can save more than $11? You can find the corresponding connections below.
    • FlixBus
      9h 25m
      0
      5:00 AM
      Windsor, ON
      International Transit Terminal
      12:40 PM
      Gary, IN
      Adam Benjamin JR Metro Center
      0
      FlixBus
      Economy
      $34
      • Waiting Time 0h 5m
    • FlixBus
      0h 40m
      0
      12:45 PM
      Gary, IN
      Adam Benjamin JR Metro Center
      1:25 PM
      Chicago
      Downtown Bus Station
      0
      FlixBus
      Economy
      $5
    Travel time is 2h 10m longer, but you will save $11

Cheapest bus trips Saturday

Mode of Transport BertCompanyCountOneCompanyName Duration Departure time From Departure Arrival time To Destination Logo Seat classes Price
FlixBus 9h 25m 5:00 AM Windsor, ON International Transit Terminal 1:25 PM Chicago 95th Red Line Station  Economy $48
FlixBus 7h 15m 5:00 AM Windsor, ON International Transit Terminal 11:15 AM Chicago Downtown Bus Station  Economy $50
FlixBus 10h 5m 8:30 AM Windsor, ON International Transit Terminal 5:35 PM Chicago Downtown Bus Station  Economy $50
FlixBus 8h 15m 2:10 PM Windsor, ON International Transit Terminal 9:25 PM Chicago Downtown Bus Station  Economy $50
FlixBus 9h 50m 8:35 PM Windsor, ON International Transit Terminal 5:25 AM Chicago Downtown Bus Station  Economy $50
  • Did you know that if you travel from Windsor, ON to Chicago via Detroit, you can save more than $11? You will find the corresponding connections below.
    • Save more than 23%
      6h 5m
      Windsor, ON
      2 mi
      4:20 PM
      Detroit
      Central Bus Station
      9:25 PM
      Chicago
      Downtown Bus Station
      0 mi
      Economy
      $37
  • Did you know that if you travel from Windsor, ON to Chicago via Gary, IN, you can save more than $8? You can find the corresponding connections below.
    • FlixBus
      8h 15m
      0
      2:10 PM
      Windsor, ON
      International Transit Terminal
      8:30 PM
      Gary, IN
      Adam Benjamin JR Metro Center
      0
      FlixBus
      Economy
      $35
      • Waiting Time 0h 15m
    • Greyhound US
      0h 40m
      0
      8:45 PM
      Gary, IN
      Adam Benjamin JR Metro Center
      9:25 PM
      Chicago
      Downtown Bus Station
      0
      Greyhound US
      Economy
      $5
    Travel time is 2h 0m longer, but you will save $8

Cheapest bus trips Sunday

Mode of Transport BertCompanyCountOneCompanyName Duration Departure time From Departure Arrival time To Destination Logo Seat classes Price
FlixBus 9h 25m 5:00 AM Windsor, ON International Transit Terminal 1:25 PM Chicago 95th Red Line Station  Economy $47
FlixBus 7h 15m 5:00 AM Windsor, ON International Transit Terminal 11:15 AM Chicago Downtown Bus Station  Economy $47
FlixBus 10h 5m 8:30 AM Windsor, ON International Transit Terminal 5:35 PM Chicago Downtown Bus Station  Economy $47
FlixBus 8h 15m 2:10 PM Windsor, ON International Transit Terminal 9:25 PM Chicago Downtown Bus Station  Economy $47
FlixBus 9h 50m 8:35 PM Windsor, ON International Transit Terminal 5:25 AM Chicago Downtown Bus Station  Economy $47
  • Did you know that if you travel from Windsor, ON to Chicago via Detroit, you can save more than $7? You will find the corresponding connections below.
    • Save more than 15%
      7h 0m
      Windsor, ON
      2 mi
      8:20 AM
      Detroit
      Central Bus Station
      2:20 PM
      Chicago
      Downtown Bus Station
      0 mi
      Economy
      $40
  • Did you know that if you travel from Windsor, ON to Chicago via Gary, IN, you can save more than $7? You can find the corresponding connections below.
    • FlixBus
      8h 15m
      0
      2:10 PM
      Windsor, ON
      International Transit Terminal
      8:30 PM
      Gary, IN
      Adam Benjamin JR Metro Center
      0
      FlixBus
      Economy
      $35
      • Waiting Time 0h 15m
    • Greyhound US
      0h 40m
      0
      8:45 PM
      Gary, IN
      Adam Benjamin JR Metro Center
      9:25 PM
      Chicago
      Downtown Bus Station
      0
      Greyhound US
      Economy
      $5
    Travel time is 2h 0m longer, but you will save $7

Cheapest bus trips Monday

Mode of Transport BertCompanyCountOneCompanyName Duration Departure time From Departure Arrival time To Destination Logo Seat classes Price
FlixBus 10h 5m 8:30 AM Windsor, ON International Transit Terminal 5:35 PM Chicago Downtown Bus Station  Economy $38
FlixBus 8h 15m 2:10 PM Windsor, ON International Transit Terminal 9:25 PM Chicago Downtown Bus Station  Economy $38
FlixBus 9h 50m 8:35 PM Windsor, ON International Transit Terminal 5:25 AM Chicago Downtown Bus Station  Economy $38
FlixBus 7h 25m 5:00 AM Windsor, ON International Transit Terminal 11:25 AM Chicago Downtown Bus Station  Economy $38
FlixBus 7h 15m 5:00 AM Windsor, ON International Transit Terminal 11:15 AM Chicago Downtown Bus Station  Economy $42

Best Price Offer: The price for the cheapest bus from Windsor, ON to Chicago is $38 on 8/31/2026. Flexible travelers save on ticket prices.


Frequency of bus connections between Windsor, ON and Chicago

See here how frequent the connections between Windsor, ON and Chicago are, during different times and days of the week.
Sunday is the busiest day, with more than 16 daily buses from Windsor, ON to Chicago. Tuesday has instead the fewest connections, with only 12 daily coaches between Windsor, ON and Chicago.
The busiest time of the day is the Afternoon, with 28 buses from Windsor, ON to Chicago, while Morning sees the fewest connections between Windsor, ON and Chicago, with 12 offers.

Facts about the bus from Windsor, ON to Chicago

Compare all providers like FlixBus that travel 13 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 6h 15m
Earliest Bus 5:00 AM
Latest Bus 8:35 PM
Daily Bus Routes 13 Ø
Distance 237.9 miles
Bus Companies FlixBus

Cheapest bus connections from Windsor, ON to Chicago

Every day, 13 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 08/25/2026 and for the following days.

Sunday
Monday
Tuesday
Wednesday
Thursday
Friday
Saturday
Sunday 08/23
Monday 08/24
Tuesday 08/25
$47
Wednesday 08/26
$44
Thursday 08/27
$41
Friday 08/28
$50
Saturday 08/29
$48
Sunday 08/30
$47
Monday 08/31
$49
Tuesday 09/01
$41
Wednesday 09/02
$39
Thursday 09/03
$40
Friday 09/04
$46
Saturday 09/05
$47
Sunday 09/06
$48
Monday 09/07
$48
Tuesday 09/08
$45
Wednesday 09/09
$40
Thursday 09/10
$54
Friday 09/11
$43
Saturday 09/12
$46
Sunday 09/13
$45
Monday 09/14
$42
Tuesday 09/15
$39
Wednesday 09/16
$39
Thursday 09/17
$41
Friday 09/18
$45
Saturday 09/19

The cheapest time to travel from Windsor, ON to Chicago

See here on which day and which time of the day you can find the cheapest bus ticket from Windsor, ON to Chicago, for the next 30 days.
With a price starting from $38, Monday is the cheapest day for a bus from Windsor, ON to Chicago. Saturday instead is the most expensive day with prices starting from $46.
Morning is the cheapest day time for bus tickets from Windsor, ON to Chicago, with $38. Morning is the most expensive time of the day with prices starting from $38.

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.

Beloved bus companies from Windsor, ON to Chicago

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

FlixBus from Windsor, ON to Chicago

FlixBus

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

Cheapest Price $38
Fastest Bus 6h 15m
Earliest Bus 5:00 AM
Last Bus 8:35 PM
Daily Connections 13 Ø
Found on 8/24/2026

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.

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 6h 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 $89. 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 13 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 6h 15m. Bus tickets for this connection cost $81. 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 5:00 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.

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

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 13 daily trips between Windsor, ON and Chicago. 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 Windsor, ON to Chicago?

Prices and availability for 13 trips between Windsor, ON and Chicago 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 Windsor, ON to Chicago

Economy
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!
From Halifax, NS to Windsor, ON bus From Halifax, NS to Windsor, ON bus
From Mesa, AZ to Windsor, ON bus From Mesa, AZ to Windsor, ON bus
Bus Lexington, KY - Windsor, ON Bus Lexington, KY - Windsor, ON
Bus to Windsor, ON from Indianapolis Bus to Windsor, ON from Indianapolis
Buses Fresno, CA - Chicago Buses Fresno, CA - Chicago
Bus to Chicago from Guadalupe, NL Bus to Chicago from Guadalupe, NL
Bus Aguascalientes to Chicago Bus Aguascalientes to Chicago
Buses El Paso, TX - Chicago Buses El Paso, TX - Chicago
Popular Airport Shuttles to Windsor, ON and to Chicago
CheckMyBus › Buses in Canada › Bus to Windsor, ON › Bus to Chicago

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