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Trip Summary
3 trains operate daily from Chicago to Windsor. The train trip from Chicago to Windsor is usually about 24 hours and 20 minutes long. However, traveling on the fastest Amtrak train can get you there in as little as 21 hours and 26 minutes.
| Distance | 770 mi (1239 km) |
| Fastest train | 21h 26m |
| Lowest price | $95.00 |
| Most frequent service | Amtrak |
| Train lines | 1 |
What is the price of a train ticket from Chicago to Windsor?
Over the past month, a train ticket between Chicago, IL and Windsor, CT cost $206.67, on average. Due to the distance between Chicago and Windsor, train tickets on this route tend to be relatively pricey. Booking your trip at least 27 days in advance can help you secure tickets at the best price. For same-day bookings, you’ll likely have to pay around $192.99 more.
Average prices by travel date
For the next 30 days, the cost of a one-way train trip from Chicago to Windsor will range from $177 to $351. If you're planning to travel by train to Windsor in the upcoming week, the cheapest train ticket from Chicago you can find in the next 7 days is $195. Be sure to book your trip in advance as train ticket prices typically increase as your travel date approaches.
Monthly average prices
Prices as travel date approaches
If you're looking to save on your train trip from Chicago to Windsor, book online with Wanderu at least 27 days in advance. That way, you’ll save $192.99 compared to booking your ticket last minute.
Which train should you take from Chicago to Windsor?
Amtrak is the one and only train line which connects Chicago to Windsor. However, there are 3 trains per day to choose from.
| Train | Daily Trips | Avg. Time | Avg. Price |
|---|---|---|---|
| Amtrak | 3 | 1d 0h 21m | $242.41 |
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 3 Amtrak trains from Chicago to Windsor every day, as well as 2 trips on the weekends, with prices starting from $95.
Frequently Asked Questions
The distance between Chicago and Windsor is approximately 770 miles, or 1239 kilometers. The average train journey between these two cities takes 24 hours and 20 minutes, although the absolute fastest you could get there is 21 hours and 26 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.
Thursday tends to be the busiest day of the week with travelers taking trains from Chicago to Windsor. Ticket price also tend to be more expensive on Thursday than other days. If you are hoping to have more room on the train and even save some change check out travel options on Saturday instead, as less people travel then and deals are more likely to be found.
The earliest train departs Chicago at 6:00pm while the last train of the day leaves at 6:00pm. To see all scheduled departure times, use the search function on this page to get the full schedule for your specific travel dates.
There are 3 scheduled trains on most days. Unfortunately, none of them are direct connections, so you will need to disembark from your original train and board a connecting train during your journey. Don't forget to bring your carry-on luggage when you switch trains. In some instances, you may also be responsible for transferring your own checked baggage.
You can also take a train for your return trip from Windsor to Chicago.
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
Image credit: Unsplash
Outside of Hartford is Windsor, a charming Connecticut town that is known as the state's first English settlement. Due to this, the city has several historical sites and antique museums, like the Windsor Historical Society, The New England Air Museum, and Oliver Ellsworth Homestead, with pieces dating back to the 1700s. Outdoor enthusiasts will be pleased with the town's many parks and green spaces, from Northwest Park to the Windsor Center River Trail.
Visit Windsor just after a snowfall with your snowshoes or cross-country skis, and explore the beautiful Northwest Park. Hartford is only six minutes by train from Windsor, offering a weekend of fun and nightlife. Beer lovers can visit the iconic Back East Brewery and Thomas Hooker Brewery, while the Northwest Park Country Fair features competitions, live music, auctions, performances, and more. If you enjoy golf, check out the Keney Park Golf Course, dating back to 1927.
Windsor offers great transport links to and from other cities, especially when you're moving by train. Over 100 cities have train links through Amtrak, while a few buses also serve the town. Within Windsor, the CT-transit Hartford provides local bus service.
Station Information
Where is the train station in Chicago?
Image credit: Jeramey Jannene
Link to image attribution
Main departure station: Chicago (Union Station), Illinois
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:
Chicago (Union Station), Illinois
Where is the train station in Windsor?
Main arrival station: 41 Central St
Windsor has one train station.
All train stations in Windsor:
41 Central St
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