Next bus departures
| Operated by | Vehicle type | Departure time | Departure location | Trip duration | Arrival time | Arrival location | Recommended | Price and booking link |
|---|---|---|---|---|---|---|---|---|
FlixBus + Greyhound Lines, Inc. | Bus | Windsor (International Transit Centre) | Downtown Greyhound Station | Cheapest | ||||
 | Bus | Windsor (International Transit Centre) | Downtown Greyhound Station | Fastest | ||||
| Bus | Windsor (International Transit Centre) | Chicago 95Th & Dan Ryan | No tags |
Last refresh of the prices: Today at 6:58 AM EST.
Get from Windsor to Chicago
The journey takes about 10 hours, and with fares starting at just R 682, it presents an excellent value for a comfortable ride.
Where are the popular stops in Windsor and Chicago?
Stops in Windsor
- A300 Chatham St W, Windsor, ON N9A 0A8, Canada
- B181 Goyeau St, Windsor, ON N9A 2W3, Canada
Stops in Chicago
- A630 W Harrison St, Chicago, IL 60607, USA
- B
Chicago O'Hare International Airport
- C
Polk St & Canal St
500-536 W Polk St, Chicago IL 60607, USA - D
Tornado Bus S Kedzie Ave
2807 S Kedzie Ave, Chicago, IL 60623, USA - E
Cumberland CTA
5800 N Cumberland Ave, Chicago, IL 60631, USA - F
Turimex California Ave
2139 S California Ave, Chicago, IL 60608, USA
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Frequently asked questions about travelling from Windsor, ON, CA to Chicago by bus
How much does a bus ticket from Windsor to Chicago cost?
The bus ticket price from Windsor to Chicago starts at R 682. The best way to find cheap bus tickets from Windsor to Chicago is to book your tickets as early as possible. Prices tend to rise as your travel date approaches, so book in advance to secure the best prices!
How long is the bus ride from Windsor to Chicago?
The average travel time between Windsor and Chicago is around 10h, although the fastest bus will take about 7h 25m. This is the time it takes to travel the 387 km that separates the two cities.
How many daily bus connections are there between Windsor and Chicago?
The number of buses from Windsor to Chicago can differ depending on the day of the week. On average, there are 7 on this route. Some buses run direct routes, while others have layovers. Simplify your bus trip from Windsor to Chicago by comparing and selecting the bus that fits your travel style and budget on Busbud.
Which bus companies travel from Windsor to Chicago?
When taking the bus from Windsor to Chicago, you can travel comfortably and safely with FlixBus, Amtrak.
What are the departure and arrival stations when taking the bus from Windsor to Chicago?
Buses travelling between Windsor and Chicago leave from 300 Chatham St W or 181 Goyeau St and arrive at Downtown Greyhound Station, Chicago O'Hare International Airport, Polk St & Canal St.
Find cheapest prices for buses
Price is for a one-way ticket for one passenger and based on past searches.
The cheapest trip from Windsor, ON, CA to Chicago was searched and found on 24 Nov 2025 with a price of R 825To save money and be sure you have the best seat, it's a good idea to buy your bus tickets from Windsor, ON, CA to Chicago as early as possible.
You can expect to pay from R 825 to R 3 214 for a bus ticket from Windsor, ON, CA to Chicago based on the last 2 days. You can expect to find the cheapest price for the trip at R 861, which is on 2025-11-28.
