Lowest Prices
We partner with the top bus & train carriers to bring you the best deals.
Best Travel Options
We help you find & compare the best buses & trains in one place.
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.
Trip Summary
There are 5 daily trains from Windsor to Chicago. Traveling by train from Windsor to Chicago usually takes around 25 hours and 26 minutes, but the fastest Amtrak train can make the trip in 23 hours and 14 minutes.
| Distance | 770 mi (1239 km) |
| Fastest train | 23h 14m |
| Lowest price | $129.80 |
| Most frequent service | Amtrak |
| Train lines | 1 |
What is the price of a train ticket from Windsor to Chicago?
The average price for a train ticket from Windsor, CT to Chicago, IL is $222.71, Tickets are generally pricier for this train route, which is to be expected given the long distance. By booking your trip at least 21 days in advance, you increase your chances of scoring even cheaper tickets. But if you wait until the day of your trip to book tickets, expect to pay $226.40 more.
Monthly average prices
Prices as travel date approaches
If you want to score the best deal, you should plan to book your train trip online on Wanderu at least 21 days ahead of time. If you do that, your train ticket to Chicago from Windsor will be about C$226.40 cheaper compared to what you would pay if you book at the last minute.
Which train should you take from Windsor to Chicago?
Amtrak is the one and only train line which connects Windsor to Chicago. However, there are 5 trains per day to choose from.
| Train | Daily Trips | Avg. Time | Avg. Price |
|---|---|---|---|
| Amtrak | 5 | 1d 1h 26m | $322.89 |
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 5 Amtrak trains from Windsor to Chicago every day, as well as 4 trips on the weekends, with prices starting from $130.
Frequently Asked Questions
The distance between Windsor and Chicago is approximately 770 miles, or 1239 kilometers. The average train journey between these two cities takes 25 hours and 26 minutes, although the absolute fastest you could get there is 23 hours and 14 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.
On a weekly basis, the greatest number of passengers tend to travel by trains from Windsor to Chicago on Friday. Tickets for Friday tend to also be the most expensive. For savvy travelers looking for cheaper priced tickets search for travel departing on Monday. Monday also tend to have less passengers which may make boarding faster and let you snag your perfect seat.
The earliest train departs Windsor at 5:00am while the last train of the day leaves at 11:00am. 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 5 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 Chicago to Windsor.
City Information
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.
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: 41 Central St
There is one train station in Windsor.
All train stations in Windsor:
41 Central St
Where is the train station in Chicago?
Image credit: Jeramey Jannene
Link to image attribution
Main arrival 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.
Train stations in Chicago:
Chicago (Union Station), Illinois
Get around town with Moovit
Need a return trip from Chicago to Windsor?
Search Train TicketsPlan your next adventure
More trains from Windsor
Continue by train from Chicago
Check out these popular routes
Wanderu is the simplest way to book bus and train travel.
With just a quick search on Wanderu, you can compare bus and train schedules 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 bus and train tickets hassle-free and with no additional fees. Most importantly, as Wanderu is an official partner of all leading bus and train companies, we always have the best bus and train deals out there.
Book buses and trains on the go with the Wanderu app.
Download our app and snag the best travel deals across North America & Europe.Learn more