Next departures to Chicago
One passenger / one way
- This trip is recommended because it is: CheapestDeparture time: June 21 atDeparture city: WindsorDeparture location: International Transit TerminalArrival time: June 21 atDestination city: ChicagoDestination location: Chicago (Union Station), ILOperated by: Amtrak
Vehicle: BusDuration: - This trip is recommended because it is: FastestDeparture time: June 21 atDeparture city: WindsorDeparture location: Windsor (International Transit Centre)Arrival time: June 21 atDestination city: ChicagoDestination location: Downtown Greyhound StationOperated by: FlixBus
Vehicle: BusDuration: - Departure time: June 21 atDeparture city: WindsorDeparture location: Windsor (International Transit Centre)Arrival time: June 21 atDestination city: ChicagoDestination location: Downtown Greyhound StationOperated by: FlixBusVehicle: BusDuration:
- Departure time: June 21 atDeparture city: WindsorDeparture location: International Transit TerminalArrival time: June 21 atDestination city: ChicagoDestination location: Chicago (Union Station), ILOperated by: AmtrakVehicle: BusDuration:
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Bus Windsor to Chicago: Trip Overview
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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.
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 for your trip Windsor, ON, CA - 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 to Chicago was searched and found on Jun 24, 2025 with a price of $41To 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 $41 to $128 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 $41 which is on 2025-06-24.
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 one of the smallest carbon footprints of motorized transport modes. A bus going from Windsor to Chicago will emit less CO2 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 traveled bus routes
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Busbud makes bus travel easy. We help travelers 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.