Compare all timetables for the bus from Chicago to Windsor, ON
| Mode of Transport | BertCompanyCountOneCompanyName | Duration | Departure time | From | Departure | Arrival time | To | Destination | Logo | Seat classes | Price | |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Greyhound US | 9h 0m | 6:55 AM | Chicago | Downtown Bus Station | 4:55 PM | Windsor, ON | International Transit Terminal | Economy | $45 |
A Bus from Greyhound US goes from Downtown Bus Station, Chicago (USA) at 1/28/2026 6:55:00 AM to International Transit Terminal, Windsor, ON (Canada) arriving at 1/28/2026 4:55:00 PM. 50 Economy ticket for $45 per person are available. Travel duration is 9h 0m
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| Greyhound US | 11h 50m | 11:35 PM | Chicago | Downtown Bus Station | 12:25 PM | Windsor, ON | International Transit Terminal | Economy | $45 |
A Bus from Greyhound US goes from Downtown Bus Station, Chicago (USA) at 1/28/2026 11:35:00 PM to International Transit Terminal, Windsor, ON (Canada) arriving at 1/29/2026 12:25:00 PM. 50 Economy ticket for $45 per person are available. Travel duration is 11h 50m
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| FlixBus | 16h 0m | 7:25 PM | Chicago | 95th Red Line Station | 12:25 PM | Windsor, ON | International Transit Terminal | Economy | $53 |
A Bus from FlixBus goes from 95th Red Line Station, Chicago (USA) at 1/28/2026 7:25:00 PM to International Transit Terminal, Windsor, ON (Canada) arriving at 1/29/2026 12:25:00 PM. 50 Economy ticket for $53 per person are available. Travel duration is 16h 0m
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Save more than 80%0h 40m0 mi6:45 AMDetroitCentral Bus Station7:25 AMWindsor, ONInternational Transit Terminal237 miChicagoEconomyA Bus from goes from Central Bus Station, Detroit (USA) at 1/28/2026 6:45:00 AM to International Transit Terminal, Windsor, ON (Canada) arriving at 1/28/2026 7:25:00 AM. 50 Economy ticket for $9 per person are available. Travel duration is 0h 40m
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| Mode of Transport | BertCompanyCountOneCompanyName | Duration | Departure time | From | Departure | Arrival time | To | Destination | Logo | Seat classes | Price | |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Greyhound US | 9h 0m | 6:55 AM | Chicago | Downtown Bus Station | 4:55 PM | Windsor, ON | International Transit Terminal | Economy | $31 |
A Bus from Greyhound US goes from Downtown Bus Station, Chicago (USA) at 1/29/2026 6:55:00 AM to International Transit Terminal, Windsor, ON (Canada) arriving at 1/29/2026 4:55:00 PM. 50 Economy ticket for $31 per person are available. Travel duration is 9h 0m
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| Greyhound US | 11h 50m | 11:35 PM | Chicago | Downtown Bus Station | 12:25 PM | Windsor, ON | International Transit Terminal | Economy | $32 |
A Bus from Greyhound US goes from Downtown Bus Station, Chicago (USA) at 1/29/2026 11:35:00 PM to International Transit Terminal, Windsor, ON (Canada) arriving at 1/30/2026 12:25:00 PM. 50 Economy ticket for $32 per person are available. Travel duration is 11h 50m
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| FlixBus | 10h 10m | 5:45 AM | Chicago | 95th Red Line Station | 4:55 PM | Windsor, ON | International Transit Terminal | Economy | $52 |
A Bus from FlixBus goes from 95th Red Line Station, Chicago (USA) at 1/29/2026 5:45:00 AM to International Transit Terminal, Windsor, ON (Canada) arriving at 1/29/2026 4:55:00 PM. 50 Economy ticket for $52 per person are available. Travel duration is 10h 10m
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| FlixBus | 16h 0m | 7:25 PM | Chicago | 95th Red Line Station | 12:25 PM | Windsor, ON | International Transit Terminal | Economy | $53 |
A Bus from FlixBus goes from 95th Red Line Station, Chicago (USA) at 1/29/2026 7:25:00 PM to International Transit Terminal, Windsor, ON (Canada) arriving at 1/30/2026 12:25:00 PM. 50 Economy ticket for $53 per person are available. Travel duration is 16h 0m
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| Mode of Transport | BertCompanyCountOneCompanyName | Duration | Departure time | From | Departure | Arrival time | To | Destination | Logo | Seat classes | Price | |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Greyhound US | 9h 0m | 6:55 AM | Chicago | Downtown Bus Station | 4:55 PM | Windsor, ON | International Transit Terminal | Economy | $35 |
A Bus from Greyhound US goes from Downtown Bus Station, Chicago (USA) at 1/31/2026 6:55:00 AM to International Transit Terminal, Windsor, ON (Canada) arriving at 1/31/2026 4:55:00 PM. 50 Economy ticket for $35 per person are available. Travel duration is 9h 0m
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| Greyhound US | 7h 30m | 3:55 PM | Chicago | Downtown Bus Station | 12:25 AM | Windsor, ON | International Transit Terminal | Economy | $35 |
A Bus from Greyhound US goes from Downtown Bus Station, Chicago (USA) at 1/31/2026 3:55:00 PM to International Transit Terminal, Windsor, ON (Canada) arriving at 2/1/2026 12:25:00 AM. 50 Economy ticket for $35 per person are available. Travel duration is 7h 30m
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| Greyhound US | 11h 50m | 11:35 PM | Chicago | Downtown Bus Station | 12:25 PM | Windsor, ON | International Transit Terminal | Economy | $35 |
A Bus from Greyhound US goes from Downtown Bus Station, Chicago (USA) at 1/31/2026 11:35:00 PM to International Transit Terminal, Windsor, ON (Canada) arriving at 2/1/2026 12:25:00 PM. 50 Economy ticket for $35 per person are available. Travel duration is 11h 50m
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| FlixBus | 10h 10m | 5:45 AM | Chicago | 95th Red Line Station | 4:55 PM | Windsor, ON | International Transit Terminal | Economy | $52 |
A Bus from FlixBus goes from 95th Red Line Station, Chicago (USA) at 1/31/2026 5:45:00 AM to International Transit Terminal, Windsor, ON (Canada) arriving at 1/31/2026 4:55:00 PM. 50 Economy ticket for $52 per person are available. Travel duration is 10h 10m
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| FlixBus | 16h 0m | 7:25 PM | Chicago | 95th Red Line Station | 12:25 PM | Windsor, ON | International Transit Terminal | Economy | $53 |
A Bus from FlixBus goes from 95th Red Line Station, Chicago (USA) at 1/31/2026 7:25:00 PM to International Transit Terminal, Windsor, ON (Canada) arriving at 2/1/2026 12:25:00 PM. 50 Economy ticket for $53 per person are available. Travel duration is 16h 0m
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| Mode of Transport | BertCompanyCountOneCompanyName | Duration | Departure time | From | Departure | Arrival time | To | Destination | Logo | Seat classes | Price | |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Greyhound US | 9h 0m | 6:55 AM | Chicago | Downtown Bus Station | 4:55 PM | Windsor, ON | International Transit Terminal | Economy | $41 |
A Bus from Greyhound US goes from Downtown Bus Station, Chicago (USA) at 2/1/2026 6:55:00 AM to International Transit Terminal, Windsor, ON (Canada) arriving at 2/1/2026 4:55:00 PM. 50 Economy ticket for $41 per person are available. Travel duration is 9h 0m
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| Greyhound US | 7h 30m | 3:55 PM | Chicago | Downtown Bus Station | 12:25 AM | Windsor, ON | International Transit Terminal | Economy | $41 |
A Bus from Greyhound US goes from Downtown Bus Station, Chicago (USA) at 2/1/2026 3:55:00 PM to International Transit Terminal, Windsor, ON (Canada) arriving at 2/2/2026 12:25:00 AM. 50 Economy ticket for $41 per person are available. Travel duration is 7h 30m
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| Greyhound US | 11h 50m | 11:35 PM | Chicago | Downtown Bus Station | 12:25 PM | Windsor, ON | International Transit Terminal | Economy | $41 |
A Bus from Greyhound US goes from Downtown Bus Station, Chicago (USA) at 2/1/2026 11:35:00 PM to International Transit Terminal, Windsor, ON (Canada) arriving at 2/2/2026 12:25:00 PM. 50 Economy ticket for $41 per person are available. Travel duration is 11h 50m
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| FlixBus | 10h 10m | 5:45 AM | Chicago | 95th Red Line Station | 4:55 PM | Windsor, ON | International Transit Terminal | Economy | $52 |
A Bus from FlixBus goes from 95th Red Line Station, Chicago (USA) at 2/1/2026 5:45:00 AM to International Transit Terminal, Windsor, ON (Canada) arriving at 2/1/2026 4:55:00 PM. 50 Economy ticket for $52 per person are available. Travel duration is 10h 10m
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| FlixBus | 16h 0m | 7:25 PM | Chicago | 95th Red Line Station | 12:25 PM | Windsor, ON | International Transit Terminal | Economy | $53 |
A Bus from FlixBus goes from 95th Red Line Station, Chicago (USA) at 2/1/2026 7:25:00 PM to International Transit Terminal, Windsor, ON (Canada) arriving at 2/2/2026 12:25:00 PM. 50 Economy ticket for $53 per person are available. Travel duration is 16h 0m
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| 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 | $38 |
A Bus from Greyhound US goes from Downtown Bus Station, Chicago (USA) at 2/2/2026 3:55:00 PM to International Transit Terminal, Windsor, ON (Canada) arriving at 2/3/2026 12:25:00 AM. 50 Economy ticket for $38 per person are available. Travel duration is 7h 30m
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| Greyhound US | 9h 0m | 6:55 AM | Chicago | Downtown Bus Station | 4:55 PM | Windsor, ON | International Transit Terminal | Economy | $39 |
A Bus from Greyhound US goes from Downtown Bus Station, Chicago (USA) at 2/2/2026 6:55:00 AM to International Transit Terminal, Windsor, ON (Canada) arriving at 2/2/2026 4:55:00 PM. 50 Economy ticket for $39 per person are available. Travel duration is 9h 0m
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| Greyhound US | 13h 25m | 10:00 AM | Chicago | Canal & Van Buren | 12:25 AM | Windsor, ON | International Transit Terminal | Economy | $48 |
A Bus from Greyhound US goes from Canal & Van Buren, Chicago (USA) at 2/2/2026 10:00:00 AM to International Transit Terminal, Windsor, ON (Canada) arriving at 2/3/2026 12:25:00 AM. 50 Economy ticket for $48 per person are available. Travel duration is 13h 25m
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| FlixBus | 10h 10m | 5:45 AM | Chicago | 95th Red Line Station | 4:55 PM | Windsor, ON | International Transit Terminal | Economy | $55 |
A Bus from FlixBus goes from 95th Red Line Station, Chicago (USA) at 2/2/2026 5:45:00 AM to International Transit Terminal, Windsor, ON (Canada) arriving at 2/2/2026 4:55:00 PM. 50 Economy ticket for $55 per person are available. Travel duration is 10h 10m
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Best Price Offer: The price for the cheapest bus from Chicago to Windsor, ON is $31 on 1/29/2026. Flexible travelers save on ticket prices.
Frequency of bus connections between Chicago and Windsor, ON
Facts about the bus from Chicago to Windsor, ON
Compare all providers like Greyhound US and FlixBus that travel 10 times every day by bus from Chicago to Windsor, ON in one click! Book your bus ticket from Chicago to Windsor, ON starting from $31!
| Cheapest Bus | $31 |
| Fastest Bus | 8h 30m |
| Earliest Bus | 6:55 AM |
| Latest Bus | 3:55 PM |
| Daily Bus Routes | 10 Ø |
| Distance | 237.9 miles |
| Bus Companies | Greyhound US and FlixBus |
Cheapest bus connections from Chicago to Windsor, ON
Every day, 10 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 01/27/2026 and for the following days.
The cheapest time to travel from Chicago to Windsor, ON
How to save money travelling from Chicago to Windsor, ON
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
Greyhound US from Chicago to Windsor, ON
Here you will find the key facts about the Greyhound US bus route Chicago to Windsor, ON:
| Cheapest Price | $31 |
| Fastest Bus | 8h 30m |
| Earliest Bus | 6:55 AM |
| Last Bus | 3:55 PM |
| Daily Connections | 7 Ø |
| Found on | 1/23/2026 |
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
FAQs about the Chicago to Windsor, ON bus
How much does a Chicago Windsor, ON bus trip cost?
How much could I save by comparing buses from Chicago to Windsor, ON?
On average, how many connections are available from Chicago to Windsor, ON each day?
How long does a bus journey from Chicago to Windsor, ON take?
What time is the first bus from Chicago to Windsor, ON?
What time is the last bus from Chicago to Windsor, ON?
Which bus companies operate the Chicago Windsor, ON route?
Is there a direct bus between Chicago and Windsor, ON?
What can I take with me on the Chicago to Windsor, ON bus route?
What equipment is available for the Chicago Windsor, ON bus route?
How does CheckMyBus find the best bus deals from Chicago to Windsor, ON?
How does CheckMyBus technology work for trips from Chicago to Windsor, ON?
Available seat classes which are offered on the bus route Chicago to Windsor, ON
The cheapest option available for your ticket, it usually comes with reclinable seats and AC.
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