Next departures to Chicago
One passenger / one way
- This trip is recommended because it is the: Cheapest + FastestDeparture time: 23 June atDeparture city: WindsorDeparture location: Windsor (International Transit Centre)Arrival time: 23 June atDestination city: ChicagoDestination location: Downtown Greyhound StationOperated by: FlixBus
Vehicle: BusDuration: - Departure time: 23 June atDeparture city: WindsorDeparture location: Windsor (International Transit Centre)Arrival time: 23 June atDestination city: ChicagoDestination location: Chicago 95Th & Dan RyanOperated by: FlixBusVehicle: BusDuration:
- Departure time: 23 June atDeparture city: WindsorDeparture location: International Transit TerminalArrival time: 23 June atDestination city: ChicagoDestination location: Chicago (Union Station), ILOperated by: Amtrak
Vehicle: BusDuration:
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Bus Windsor to Chicago: Trip Overview
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Based on 9167 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 US$43
Windsor to Chicago Bus
Busbud helps you find a bus from Windsor to Chicago. Get the best fare and schedule, book a round trip ticket or find buses with WiFi and electrical outlets.
We make sure you can find a bus service from Windsor to Chicago from the most reliable bus companies operating this trip.
Discover how much the bus trip from Windsor to Chicago will cost you. Use our filters and sorting features to find the cheapest bus tickets or luxury buses.
Where are the popular stops in Windsor and Chicago?
Frequently asked questions on the trip Windsor, ON, CA - Chicago
What's the distance between Windsor and Chicago by coach?
The distance between Windsor and Chicago by coach is approximately 240 miles (387 km).
How can I get from Windsor to Chicago without driving?
You can travel to Chicago from Windsor by coach, which provides a smooth ride and an affordable and convenient trip. You can also consider rideshare services depending on your preferences.
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 to Chicago was searched and found on 27 Jun 2025 with a price of US$39To save money and be sure you have the best seat, it's a good idea to buy your bus tickets from Windsor to Chicago as early as possible.
You can expect to pay from US$39 to US$113 for a bus ticket from Windsor to Chicago based on the last 2 days. You can expect to find the cheapest price for the trip at US$39, which is on 2025-06-27.
Usually Amtrak will charge you higher prices for tickets closer to the departure date. To find the best prices, you should be flexible on your date of travel.
About Bus Travel
Bus Travel Tips
Make friends with the driver. They usually know a lot about your destination and may even recommend which side of the bus to sit on to get the best views on the road between Windsor and Chicago!
Start sightseeing the minute your bus leaves the station. If you're on the night bus from Windsor to Chicago, get comfy and count the stars.
Buses have the smallest carbon footprint of all motorized transport modes. A bus going from Windsor to Chicago will emit half the CO2 emitted by a train, and radically less than a car or an airplane.
Make a music playlist for your bus ride from Windsor to Chicago, and enjoy the scenery to tunes from your own personal soundtrack.
Did you know?
The bus driver with the longest career in the world drove more than 2,000,000 miles and is a happy World Record holder.
Did you know there are on average 4,400 intercity bus departures every day in the US only? This number has been growing for 9 years in a row, yay!
One of the longest bus route in the world goes all the way from Ontario to Alberta in Canada (with the same bus). This trip is 3,435 km or 2,135 miles long and the price is a bit under $100.
Top travelled bus routes
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Busbud makes bus travel easy. We help travellers find a bus, plot routes, and book intercity bus tickets all over the world. With Busbud, wherever you go, you have a worldwide bus station within reach and available in your own language and currency. With Busbud, you can buy tickets with confidence. We ensure that you make the most out of your bus trip by partnering up with reliable bus companies from all around the world such as Greyhound, Eurolines, ALSA, OUIBUS (BlaBlaBus), National Express and many others.