Find coaches from Windsor, ON, CA to Chicago

Next departures

Next departures from Windsor to Chicago on 31 October
Operated byVehicle typeDeparture timeDeparture locationTrip durationArrival timeArrival locationRecommendedPrice and booking link
FlixBus + Greyhound Lines, Inc.
Windsor (International Transit Centre)
Downtown Greyhound StationCheapest
FlixBus
Windsor (International Transit Centre)
Downtown Greyhound StationFastest
FlixBus + Greyhound Lines, Inc.
Windsor (International Transit Centre)
Downtown Greyhound StationNo tags
FlixBus
Windsor (International Transit Centre)
Chicago 95Th & Dan RyanNo tags
FlixBus + Greyhound Lines, Inc.
Windsor (International Transit Centre)
Chicago 95Th & Dan RyanNo tags

Last refresh of the prices: Yesterday at 11:12 PM EDT.

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Get from Windsor to Chicago

busbud logoThis route is served by bus only

The journey takes about 10 hours, and with fares starting at just US$45, it presents an excellent value for a comfortable ride.

6bus per day
10hAverage duration
383 kmDistance
10kgCO₂ emissions

Bus Windsor, ON, CA to Chicago: Trip Overview

Average ticket priceUS$68
Average bus trip duration10h
Number of daily buses6
Earliest bus departure05:00
Distance383 km
Latest bus departure20:35

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.

Frequently asked questions on the trip Windsor, ON, CA - Chicago

  1. How much does a bus ticket from Windsor to Chicago cost?

    The bus ticket price from Windsor to Chicago starts at US$45. The best way to find cheap bus tickets from Windsor to Chicago is to book your tickets as early as possible. Prices tend to rise as your travel date approaches, so book in advance to secure the best prices!

  2. How long is the bus ride from Windsor to Chicago?

    The average travel time between Windsor and Chicago is around 10h, although the fastest bus will take about 7h 25m. This is the time it takes to travel the 387 km that separates the two cities.

  3. How many daily bus connections are there between Windsor and Chicago?

    The number of buses from Windsor to Chicago can differ depending on the day of the week. On average, there are 6 on this route. Some buses run direct routes, while others have layovers. Simplify your bus trip from Windsor to Chicago by comparing and selecting the bus that fits your travel style and budget on Busbud.

  4. Which bus companies travel from Windsor to Chicago?

    When taking the bus from Windsor to Chicago, you can travel comfortably and safely with FlixBus, Amtrak.

  5. What are the departure and arrival stations when taking the bus from Windsor to Chicago?

    Buses travelling between Windsor and Chicago leave from 300 Chatham St W or 181 Goyeau St and arrive at Downtown Greyhound Station, Chicago O'Hare International Airport, Polk St & Canal St.

Find cheapest prices for buses

Price is for a one-way ticket for one passenger and based on past searches.

Best price found
28/10
US$45
29/10
No data
Today
No data
31/10
US$56
01/11
US$49
02/11
No data
03/11
US$40
04/11
US$42
busbud logoThe cheapest trip from Windsor, ON, CA to Chicago was searched and found on 03 Nov 2025 with a price of US$40

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 US$40 to US$61 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 US$40, which is on 2025-11-03.

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.

Will you be returning to Windsor, ON, CA by bus?

Bus from Chicago to Windsor, ON, CA

Why choose Busbud?

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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.

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