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Windsor to Chicago train

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Windsor - Chicago Train Schedule

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Trip Summary

There is one daily train from Windsor to Chicago. Traveling by train from Windsor to Chicago usually takes 9 hours and 40 minutes, but some trains might arrive slightly earlier or later than scheduled.

Distance237 mi (382 km)
Fastest train9h 40m
Lowest price$45.00
Most frequent serviceAmtrak
Train lines1

Which train should you take from Windsor to Chicago?

Amtrak is the one and only train line which connects Windsor to Chicago. Furthermore, there is only one train per day, so you will have to plan your travel around this limited availability. On the other hand, you won't have to spend a ton of time comparing a bunch of possible options.

TrainDaily TripsAvg. TimeAvg. Price
Amtrak19h 40m$45.00
  • Amtrak is the largest passenger railroad service in America, offering daily intercity trains to hundreds of destinations across the contiguous United States, as well as several cities in Canada. Every Amtrak train comes equipped with comfortable seats with extra legroom, as well as several four-seat areas with tables in the middle. In addition, each car has a freshly cleaned restroom, free WiFi and power outlets at every seat. There are also snack bars where you can purchase drinks or food during your journey. On average, there are 1 Amtrak trains from Windsor to Chicago every day, as well as 0 trips on the weekends, with prices starting from $45.

Frequently Asked Questions

While the train is the main method of transportation from Windsor to Chicago, it will only take you part of the way there. Please note that part of your trip will be on a different vehicle, most commonly a bus or express shuttle.

The distance between Windsor and Chicago is approximately 237 miles, or 382 kilometers. The average train journey between these two cities takes 9 hours and 40 minutes,

Looking for ways to pass the time? Most trains are equipped with Wi-Fi, which means you can stream music, browse social media or get some work done during your ride. That said, in case your train has a spotty signal, or is among the few without Wi-Fi, we also recommend downloading TV shows and movies to your mobile device in advance of your trip. That way the ride will fly by whatever the Wi-Fi situation.

Friday tends to be the busiest day of the week with travelers taking trains from Windsor to Chicago. Ticket price also tend to be more expensive on Friday than other days. If you are hoping to have more room on the train and even save some change check out travel options on Friday instead, as less people travel then and deals are more likely to be found.

Most days, there is only one train which leaves Windsor at 2:00pm and arrives in Chicago around 9 hours later.

Typically there is only one scheduled train per day. However, it is not a direct train. This means that you will need to disembark from your original train and board a connecting train at some point during your journey. You will need to remember to bring your carry-on luggage with you when you transfer trains. Depending on the carrier's policy, you may also be responsible for transferring your own checked baggage.

You can also take a train for your return trip from Chicago to Windsor.

City Information

Windsor

Windsor, ON - CAXEC-0Windsor, ON - CAXEC-1Windsor, ON - CAXEC-2

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.

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.

Station Information

Where is the train station in Windsor?

Main departure station: Transit Centre

There is one train station in Windsor.

All train stations in Windsor:

  • Transit Centre

Where is the train station in Chicago?

Chicago, IL - Union Station - CHIUST-0

Image credit: Jeramey Jannene

Link to image attribution

Main arrival station: Union Station

The historic Chicago Union Station is the United States' third busiest train station and a hub for 15 Amtrak train lines with destinations throughout the country. The station also serves bus carriers like Greyhound, Indian Trails and Jefferson Lines, and offers connections to Metra commuter lines. Union Station is also just a quick walk to the nearest Chicago L lines. The current station was built in 1925, to replace the original one dating back to 1881, and today wows visitors with its impressive facade, massive columns, and opulent Great Hall. Located right in downtown and adjacent to the Chicago Loop, Union Station is equipped with many services and amenities, including phone charging stations, shops, and various food and drink options.

All train stations in Chicago:

  • Union Station

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