Next bus departures
| Operated by | Vehicle type | Departure time | Departure location | Trip duration | Arrival time | Arrival location | Recommended | Price and booking link |
|---|---|---|---|---|---|---|---|---|
 | Bus | Windsor (International Transit Centre) | Chicago 95Th & Dan Ryan | Cheapest | ||||
| Bus | Windsor (International Transit Centre) | Downtown Greyhound Station | Fastest | ||||
| Bus | Windsor (International Transit Centre) | Downtown Greyhound Station | No tags | ||||
FlixBus + Greyhound Lines, Inc. | Bus | Windsor (International Transit Centre) | Downtown Greyhound Station | No tags | ||||
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) | Chicago 95Th & Dan Ryan | No tags | ||||
FlixBus + Greyhound Lines, Inc. + FlixBus | Bus | Windsor (International Transit Centre) | Chicago 95Th & Dan Ryan | No tags |
Last refresh of the prices: Today at 2:58 AM EDT.
Get from Windsor to Chicago
The journey takes about 9 hours 50 minutes, and with fares starting at just ARS 62,028, it presents an excellent value for a comfortable ride.
Bus stations and stops in Windsor and Chicago
Stops in Windsor
- A
181 Goyeau St
181 Goyeau St, Windsor, ON N9A 2W3, Canada - B
300 Chatham St W
300 Chatham St W, Windsor, ON N9A 0A8, Canada
Stops in Chicago
- A
Downtown Greyhound Station
630 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
Based on 13056 reviews, the company was rated 3.5 stars on Busbud. Travellers were especially satisfied with the ticket access and the temperature but often complained with the Wi‑Fi. FlixBus ticket prices on this trip start at ARS 64,860
Frequently asked questions about travelling 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 ARS 62,028. The average price for this route is around ARS 88,066. 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 travel time from Windsor to Chicago is 9h 50m, covering a distance of 384 km. The quickest bus can get you there in 7h 15m and is operated by FlixBus.
Which bus companies service the Windsor to Chicago route?
Several major bus companies operate on this route with 10 buses available per day.
What are the earliest and latest departure times 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 9.5861 kg of CO₂, making it a highly eco-friendly travel option and a mode of travel recommended by Busbud.
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 Jul 22, 2026 with a price of ARS 60,559To 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 ARS 60,559 to ARS 157,500 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 ARS 60,559 which is on 2026-07-22.
