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Journey Information
There are 13 intercity buses per day from Chicago to Windsor. Traveling by bus from Chicago to Windsor usually takes around 10 hours and 9 minutes, but the fastest Greyhound bus can make the trip in 6 hours and 55 minutes.
| Distance | 237 mi (382 km) |
| Shortest duration | 6h 55m |
| Cheapest price | $28.27 |
| Most frequent service | Greyhound |
| Bus lines | 2 |
How much is a bus ticket from Chicago to Windsor?
Bus tickets for a trip from Chicago to Windsor cost $43.95 on average. Tickets cheaper than $43.95 are an excellent bargain. If you book your trip ahead of time using Wanderu, you can easily find bus tickets at or below this price.
Average prices by travel date
If you're planning to travel by bus from Chicago to Windsor in the next month, the average ticket price is expected to range from $40 to $49. The cheapest bus tickets available in the next few weeks are for trips departing on May 9, 2024.
If you’re looking to travel to Windsor this week, bus tickets are available starting at $43.
Monthly avg. prices
Prices as travel date approaches
The easiest way to save money on bus tickets is by booking in advance! Many carriers increase prices as the travel date approaches, so it's always a good idea to buy your tickets as early as possible. Book at least 22 days in advance to save $31.16 or more on your ticket, compared to booking at the last minute.
What bus companies travel from Chicago to Windsor?
There are two bus lines that have daily service from Chicago to Windsor that you can compare and book on Wanderu. Of these two carriers, Greyhound usually offers more choice, with 13 scheduled trips per day.
| Bus | Daily Trips | Avg. Time | Avg. Price |
|---|---|---|---|
| FlixBus US | 1 | 9h 31m | $62.35 |
| Greyhound | 13 | 10h 9m | $47.75 |
FlixBus US is the American branch of German bus company FlixBus, known for providing sustainable, affordable, and modern bus travel. The company offers cheap bus tickets to popular urban destinations throughout the United States. FlixBus US buses include many amenities, including comfortable seats, free WiFi, power outlets at every seat, and an online portal for free entertainment. On average, FlixBus US operates 1 trips per day from Chicago to Windsor, and the average ticket for this route costs only .
Greyhound is the largest nationwide bus carrier in the United States, offering cheap, safe and reliable service across the country. Greyhound has become a household name, serving over 16 million passengers per year with daily trips to over 2,400 destinations. Greyhound performs about 13 bus trips from Chicago to Windsor every day, with the average journey taking around 10 hours and 9 minutes to complete. Bus tickets for Greyhound trips to Windsor usually start from $28.
Frequently Asked Questions
The bus takes an average of 10 hours and 9 minutes to cover the 237 miles from Chicago to Windsor. However, the fastest bus only takes 6 hours and 55 minutes. It’s definitely on the longer side, so plan to get comfortable for a long road trip. Keep in mind that your actual bus may arrive earlier or later than scheduled, depending on whether there is more or less traffic than usual.
Because many passengers travel from Chicago to Windsor at the beginning of the work week, Monday is usually the busiest day for buses. If you are planning to travel on a Monday, you should make sure to book tickets well in advance as they may sell out.
On the other hand, Friday is typically the least busy day for bus travel on this route. If you’re looking for a little extra space, a Friday ticket is the way to go.
The first bus leaves at 2:00am and the last bus leaves at 10:00pm. To see the times for all buses from Chicago to Windsor, enter your specific travel dates in the search bar.
There are 13 scheduled buses that travel from Chicago to Windsor every day, so you have a decent number of options to choose from. Unfortunately, none of them are direct connections, so no matter which bus you take, you will have to transfer buses at least once during your journey.
Need more travel options? Consider taking the train from Chicago to Windsor; ticket prices start at $50.00.
City Information
Chicago
Known for its innovative architecture, cultural contributions to jazz and house music, and of course that irresistible deep-dish pizza, the many sights and experiences in Chicago make it one of the best urban vacation destinations for millennials and a top destination in Illinois.
You can't beat the views of the city and Lake Michigan from the SkyDeck in the Willis Tower; at over 1,300 feet, this is the highest observation deck in the U.S. Snap that classic selfie with the Bean in Millennium Park, then wander the many museums in nearby Grant Park. Navy Pier is a popular tourist hotspot for its parks, restaurants, and attractions right on Lake Michigan, and baseball fans will find paradise in Wrigleyville, home to the Chicago Cubs' Wrigley Field and sports bars galore.
Chicago's enormous parks offer plentiful opportunities for outdoor activities in gorgeous urban settings. Many companies offer kayak rentals or boat tours on the Chicago River, with special tours running on Saint Patrick's Day, when the entire river is dyed green. When you’re ready to buy some souvenirs from your epic trip, hit the big brand stores on the Magnificent Mile, or shop local in neighborhoods like Andersonville and Wicker Park. And don't miss the chance to laugh until you cry at The Second City comedy theater, famous for launching the careers of comedians like Tina Fey and Stephen Colbert.
Chicago is one of the biggest transportation hubs in the Midwest, and provides easy access to nearby destinations ideal for day trips, as well as international travel from two airports. Thanks to plenty of bus and train stations throughout the city, getting to the Windy City is a breeze.
Windsor
Windsor is a vibrant urban community brimming with first-rate entertainment, luscious green space, and cultural delights—a city where there truly is something for everyone. Visitors can step back in time and experience Windsor's rich history through the ages at the Chimczuk Museum, Willistead Manor, and Mackenzie Hall. With 215 parks, the city is also a haven for outdoor recreation; but nowhere is better than the iconic Windsor waterfront, where strollers are spoiled for choice by a number of world-class gardens, the Ojibway Nature Centre, and the Windsor Sculpture Centre.
Known as a melting pot, Windsor is home to an eclectic blend of artistic styles and culinary surprises. For those who want a real taste of the city, catch a theatre performance at one of the many elite venues dotted around Windsor before hitting downtown to satisfy your appetite with a selection of delicious international foods.
Located across the river from Detroit, Windsor forms one half of the International Gateway between Canada and the U.S.—the second busiest border crossing in North America. The city also acts as a major jump-off point for national travel deeper into Canada via Toronto and beyond.
Station Information
Where does the bus leave from in Chicago?
Image credit: Jeramey Jannene
Link to image attributionMain departure station: Bus Station - 630 W Harrison St
Buses to Windsor leave from 3 stations in Chicago.
All bus stations in Chicago:
Bus Station - 630 W Harrison St
Dan Ryan Bus Station
Chicago Train Station Bus Stop
Where does the bus arrive in Windsor?
Main arrival station: 181 Goyeau Street
These are the two stations where buses may stop when they arrive in Windsor.
All bus stations in Windsor:
181 Goyeau Street
Windsor Transit Terminal
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