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Chicago - Winter Haven Train Schedule
- Fri
- Fri
Trip Summary
2 trains operate daily from Chicago to Winter Haven. The train trip from Chicago to Winter Haven is usually about 42 hours and 43 minutes long. However, traveling on the fastest Amtrak train can get you there in as little as 42 hours and 25 minutes.
| Distance | 1013 mi (1631 km) |
| Fastest train | 42h 25m |
| Lowest price | $337.00 |
| Most frequent service | Amtrak |
| Train lines | 1 |
What is the price of a train ticket from Chicago to Winter Haven?
Over the past month, a train ticket between Chicago and Winter Haven cost $406.00, on average. Due to the distance between Chicago and Winter Haven, train tickets on this route tend to be relatively pricey. Booking your trip at least 1 days in advance can help you secure tickets at the best price. For same-day bookings, you’ll likely have to pay around $49.14 more.
Monthly average prices
Prices as travel date approaches
By booking your train trip from Chicago to Winter Haven on Wanderu at least 1 days ahead of time, you can save about $49.14 on your ticket. Waiting until the last minute means missing out on these savings!
Which train should you take from Chicago to Winter Haven?
Amtrak is the one and only train line which connects Chicago to Winter Haven. The schedule is relatively limited as the train only runs twice a day.
| Train | Daily Trips | Avg. Time | Avg. Price |
|---|---|---|---|
| Amtrak | 2 | 1d 18h 43m | $440.73 |
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 2 Amtrak trains from Chicago to Winter Haven every day, as well as 2 trips on the weekends, with prices starting from $337.
Frequently Asked Questions
The distance between Chicago and Winter Haven is approximately 1013 miles, or 1631 kilometers. The average train journey between these two cities takes 42 hours and 43 minutes, although the absolute fastest you could get there is 42 hours and 25 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 Chicago to Winter Haven on Monday. Tickets for Monday tend to also be the most expensive. For savvy travelers looking for cheaper priced tickets search for travel departing on Thursday. Thursday also tend to have less passengers which may make boarding faster and let you snag your perfect seat.
The earliest train departs Chicago at 5:00pm 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.
Trains leave the station in Chicago twice a day, so there are a couple of options depending on your preferred travel time. However, there are no direct trains. 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 change 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 Winter Haven 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.
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 Winter Haven?
Main arrival station: 1800 7th Street SW
Winter Haven has one train station.
All train stations in Winter Haven:
1800 7th Street SW
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