Cheap coach tickets from Chicago to Windsor
Find and compare the best ground travel options in one place.
Coach from Chicago to Windsor: Journey Information
There are 8 intercity coaches per day from Chicago to Windsor. Travelling by coach from Chicago to Windsor usually takes around 10 hours and 4 minutes, but the fastest Greyhound coach can make the trip in 7 hours and 30 minutes.
- Distance
- 237 mi (382 km)
- Shortest duration
- 7h 30m
- Cheapest price
- £27.68
- Trips per day
- 8
- Most frequent service
- Greyhound
- Coach lines
- 2
Millions of travellers trust Wanderu every year to get:
Lowest Prices
We find the cheapest coach & train tickets, so you can wander for less.
Best Travel Options
We partner with 500+ carriers to bring you the most coach & train options.
Quick & Easy Booking
Book trips quickly with a simple, hassle-free checkout – online & on our app.
Fast Customer Support
We don’t monkey around. We respond within minutes to help you out.
See what travellers are saying about Wanderu:
Chicago to Windsor Coach Timetable

There are several coach options that can take you from Chicago to Windsor:
See more detailsHow much is a coach ticket from Chicago to Windsor?
Coach tickets for a trip from Chicago to Windsor cost about £41 when you book at the cheapest time, 14 days ahead. Tickets cheaper than £41 are an excellent bargain. If you book your trip ahead of time using Wanderu, you can easily find coach tickets at or below this price.
Average coach ticket prices from Chicago to Windsor by travel date
If you're planning to travel by coach from Chicago to Windsor in the next month, the average ticket price is expected to range from £32 to £54. The cheapest coach tickets available in the next few weeks are for trips departing on 18 November 2026. If you’re looking to travel to Windsor this week, coach tickets are available starting at £37.
Average coach ticket prices from Chicago to Windsor by month
Taking the coach from Chicago to Windsor is usually cheapest in February, when the average ticket price is only £40. If you're planning to take the coach from Chicago to Windsor during November, keep in mind that coach ticket prices may be higher than usual, with an average price of £49. However, booking your trip in advance can help you score a ticket at a better price.
Prices as travel date approaches
Most coach companies charge higher ticket prices closer to the date of travel, so it’s a good idea to buy your coach tickets as early as possible. To find the cheapest coach tickets, book your trip at least 14 days in advance. This way, you can save up to £10.79 on your coach ticket compared to booking last-minute.
What coach companies travel from Chicago to Windsor?
There are two coach 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 6 scheduled trips per day.
| Coach | Daily Trips | Avg. Time | Avg. Price |
|---|---|---|---|
| FlixBus US | 2 | 9h 20m | £44.71 |
| Greyhound | 6 | 10h 23m | £47.68 |
FlixBus US is the American branch of German coach company FlixBus, known for providing sustainable, affordable, and modern coach travel. The company offers cheap coach tickets to popular urban destinations throughout the United States. FlixBus US coaches include many amenities, including comfortable seats, free WiFi, power sockets at every seat, and an online portal for free entertainment. On average, FlixBus US operates 2 trips per day from Chicago to Windsor, and the average ticket for this route costs only £44.71.






Greyhound is the largest nationwide coach 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 6 coach trips from Chicago to Windsor every day, with the average journey taking around 10 hours and 23 minutes to complete. Coach tickets for Greyhound trips to Windsor usually start from £27.68.






Frequently asked questions about travelling by coach from Chicago to Windsor
There are 8 scheduled coaches 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 coach you take, you will have to transfer coaches at least once during your journey.
Trips per day
8
Direct trips
0
The coach takes an average of 10 hours and 4 minutes to cover the 237 miles from Chicago to Windsor. However, the fastest coach only takes 7 hours and 30 minutes. It’s definitely on the longer side, so plan to get comfortable for a long road trip. Keep in mind that your actual coach may arrive earlier or later than scheduled, depending on whether there is more or less traffic than usual.
Distance (mi)
237
Distance (km)
382
The first coach leaves at 4:45 and the last coach leaves at 23:35. To see the times for all coaches from Chicago to Windsor, enter your specific travel dates in the search bar.
Earliest coach
4:45am
Latest coach
11:35pm
Saturday is usually the day when coaches are busiest, as many travellers take the coach to enjoy the weekend in Windsor. If you are planning to travel on a Saturday, you should make sure to book tickets well in advance as they may sell out. On the other hand, Wednesday is typically the least busy day for coach travel on this route. If you're looking for some extra space on the coach, travelling mid-week is your best bet.
Most crowded
Saturday
Least crowded
Wednesday
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 holiday 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 neighbourhoods like Andersonville and Wicker Park. And don't miss the chance to laugh until you cry at The Second City comedy theatre, famous for launching the careers of comedians like Tina Fey and Stephen Colbert.
Chicago is one of the biggest transport 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 coach 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 pushchairs 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 coach leave from in Chicago?
Main departure station: Bus Station - 630 W Harrison St

Coaches to Windsor leave from 3 stations in Chicago.
All coach stations in Chicago:
- Bus Station - 630 W Harrison St
- Dan Ryan Bus Station
- Chicago Train Station Bus Stop
Where does the coach arrive in Windsor?
Main arrival station: Windsor International Transit Centre
All coaches from Chicago arrive at one main station in Windsor.
Coach stations in Windsor:
- Windsor International Transit Centre
Need a return trip from Windsor to Chicago?
Search Coach Tickets
Wanderu is the simplest way to book coach and train travel.
With just a quick search on Wanderu, you can compare coach and train timetables and prices from hundreds of travel companies in one convenient place to find the trip that works best for you. Wanderu’s simple checkout process makes it easy to book cheap coach and train tickets hassle-free. Most importantly, as Wanderu is an official partner of all leading coach and train companies, we always have the best coach and train deals out there.




