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Trip Summary
There are usually 2 daily train trips available from Chicago to Winter Park. Traveling by train from Chicago to Winter Park usually takes 40 hours and 6 minutes, but the fastest Amtrak train can make the trip in 38 hours and 25 minutes.
| Distance | 983 mi (1582 km) |
| Fastest train | 38h 25m |
| Lowest price | $226.00 |
| Most frequent service | Amtrak |
| Train lines | 1 |
What is the price of a train ticket from Chicago to Winter Park?
Over the past month, a train ticket between Chicago, IL and Winter Park, FL cost $281.49, on average. Due to the distance between Chicago and Winter Park, train tickets on this route tend to be relatively pricey. Booking your trip at least 26 days in advance can help you secure tickets at the best price. For same-day bookings, you’ll likely have to pay around $291.68 more.
Average prices by travel date
The average cost of a one-way train trip from Chicago to Winter Park is expected to fluctuate between $262 and $382 in the next 30 days. If you’re planning a train trip to Winter Park in the upcoming week, the cheapest price in the next 7 days for a ticket from Chicago is $270.
Monthly average prices
Prices as travel date approaches
Planning ahead pays off when it comes to booking your train trip from Chicago to Winter Park. By reserving your ticket on Wanderu at least 26 days before departure, you can save around $291.68. Don't miss out on these savings — book in advance!
Which train should you take from Chicago to Winter Park?
Amtrak is the one and only train line which connects Chicago to Winter Park. The schedule is relatively limited as the train only runs twice a day.
| Train | Daily Trips | Avg. Time | Avg. Price |
|---|---|---|---|
| Amtrak | 2 | 1d 16h 6m | $334.88 |
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 Park every day, as well as 2 trips on the weekends, with prices starting from $226.
Frequently Asked Questions
The distance between Chicago and Winter Park is approximately 983 miles, or 1582 kilometers. The average train journey between these two cities takes 40 hours and 6 minutes, although the absolute fastest you could get there is 38 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.
Wednesday tends to be the busiest day of the week with travelers taking trains from Chicago to Winter Park. Ticket price also tend to be more expensive on Wednesday 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 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 Park 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.
Winter Park
Image credit: Unsplash
Winter Park is a city in Florida outside Orlando, known for its many outdoor spaces and art and museum centers. The Albin Polasek Museum & Sculpture Gardens showcases sculptures in a lush setting, the Charles Hosmer Morse Museum of American Art is renowned for its Tiffany windows, and the Rollins Museum of Art exhibits artworks from ancient to contemporary periods.
Museums aside, Winter Park is a fabulous urban outdoor destination. Paddle through Winter Park Canals, smell the wisteria at Central Park, and relax in Kraft Azalea Garden on Lake Maitland. Winter Park's premier urban village has cypresses sweeping over red-brick streets lined with cafés, gastro pubs, and brewing companies. Walk along Park Avenue or in the Hannibal Square district for the best shopping and dining in historic settings.
Winter Park is one of the stops on Amtrak's Silver Service between New York City and Miami. FlixBus runs a few intercity bus routes directly to Winter Park, but additional bus lines go through nearby Orlando.
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 Park?
Main arrival station: 148 W Morse Blvd
Winter Park has one train station.
All train stations in Winter Park:
148 W Morse Blvd
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