Flixbus is a European bus operator that offers intercity and bus travel in over 38 countries. Known for their easy-to-spot lime green buses and for offering affordable transportation between cities in Europe and the Americas, Flixbus is a good option for those looking for an affordable, reliable bus company. In their buses, you'll find free WiFi, bathrooms, and power outlets. You can also pay extra to choose your seat and get extra legroom, or even buy a snack or drink onboard directly from the driver. You can reschedule your ticket for a small fee, which varies from $1 to $5, depending on how close you are to the departure date.
Based on 5607 reviews, the company was rated 4.1 stars on Busbud. Travelers were especially satisfied with the seats and the ticket access but often complained with the wifi. Amtrak ticket prices on this trip start at $53
Frequently asked questions about traveling from Windsor, ON, CA to Chicago by bus
How far is Windsor from Chicago?
About 240 miles (387 km) separate Windsor and Chicago.
What are the departure and arrival stations when taking the bus from Windsor to Chicago?
Most of the buses traveling from Windsor to Chicago leave from 300 Chatham St W and arrive at Downtown Greyhound Station. These are the main pick-up and drop-off locations on this route, but you can also find other options that could better fit your plans.
What are the best sights and things to do in Chicago?
Once in Chicago, you can start exploring the city and discover its surroundings. The top sights and things to do are Willis Tower (Sears Tower), Museum of Contemporary Art, Auditorium Building and Theatre, Navy Pier and Lincoln Park Zoo.
Find cheapest prices for buses
Price is for a one-way ticket for one passenger and based on past searches.
Best price found
11/24
$47
11/25
$77
Today
No data
11/27
No data
11/28
$49
11/29
$49
11/30
$159
12/01
$73
The cheapest trip from Windsor, ON, CA to Chicago was searched and found on Nov 24, 2025 with a price of $47
To 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 $49 which is on 2025-11-28.
The cheapest trip from Windsor, ON, CA to Chicago was searched and found on Nov 24, 2025 with a price of $47
