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) | Chicago 95Th & Dan Ryan | Cheapest | ||||
 | Bus | Windsor (International Transit Centre) | Downtown Greyhound Station | Fastest | ||||
FlixBus + Greyhound Lines, Inc. | Bus | Windsor (International Transit Centre) | Downtown Greyhound Station | No tags | ||||
| Bus | Windsor (International Transit Centre) | Chicago 95Th & Dan Ryan | No tags | ||||
FlixBus + Greyhound Lines, Inc. | Bus | Windsor (International Transit Centre) | Downtown Greyhound Station | No tags |
Last refresh of the prices: Last Saturday at 2:31 PM EST.
Get from Windsor to Chicago
The journey takes about 10 hours, and with fares starting at just $57, 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 travelling from Windsor, ON, CA to Chicago by bus
How far is Windsor from Chicago?
The distance covered from Windsor to Chicago is 387 km (240 miles).
What are the departure and arrival locations for buses traveling from Windsor to Chicago?
Buses traveling this route start their trip at 300 Chatham St W, in Windsor, and end it at Downtown Greyhound Station, in Chicago.
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 18, 2025 with a price of $68To 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 $68 to $133 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 $68 which is on 2025-11-22.
