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: Yesterday at 11:57 PM EST.
Get from Windsor to Chicago
The journey takes about 10 hours and with fares starting at just $39, 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
- 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
Compare bus companies
Frequently asked questions about traveling from Windsor, ON, CA to Chicago by bus
Please note that schedules, routes, or operator details shown here may be updated or vary at the time of your trip.
How much is the bus ticket from Windsor to Chicago?
The cheapest bus tickets from Windsor to Chicago start from $39. The average price for this route is around $60. Busbud recommends that you book your tickets in advance for a better chance to get the lowest possible price.
How long is the bus ride from Windsor to Chicago?
The average bus trip duration from Windsor to Chicago is 10h, covering a distance of 239 miles (385 km). The quickest bus can get you there in 7h 25m and is operated by FlixBus.
Which bus companies service the Windsor to Chicago route?
What is the earliest and latest departure time for the bus from Windsor to Chicago?
The earliest bus departs from Windsor to Chicago at 5:00am. And the latest bus departs at 8:35pm.
What are the CO₂ emissions for the bus trip from Windsor to Chicago?
A bus trip from Windsor to Chicago generates an estimated 10 kg of CO₂, making it a highly eco-friendly travel option and recommended mode of travel by Busbud.
What is the best bus company from Windsor to Chicago?
According to Busbud customers, the highest-rated bus company on this route is Amtrak, with an average rating of 4.1 out of 5 stars based on 5597 reviews.
Which bus company has the best Wi-Fi from Windsor to Chicago?
Based on reviews on Busbud, the bus company Amtrak has the best Wi-Fi rating with a score of 3.6.
Which bus company has the most timely service from Windsor to Chicago?
According to Busbud traveller reviews, the most timely bus company on this route is FlixBus, with a punctuality rating of 3.9 out of 5 stars.
Which bus company has the cleanest buses from Windsor to Chicago?
According to Busbud traveller reviews, the bus company with the cleanest buses on this route is Amtrak, with a cleanliness rating of 4.5 out of 5 stars.
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 Nov 28, 2025 with a price of $47To 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 $47 to $183 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 $47 which is on 2025-12-05.
