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Trip Summary
2 trains operate daily from Chicago to Kissimmee. The train trip from Chicago to Kissimmee is usually about 41 hours and 11 minutes long. However, traveling on the fastest Amtrak train can get you there in as little as 39 hours and 26 minutes.
| Distance | 1002 mi (1612 km) |
| Fastest train | 39h 26m |
| Lowest price | $345.13 |
| Most frequent service | Amtrak |
| Train lines | 1 |
What is the price of a train ticket from Chicago to Kissimmee?
In the last 30 days, the average cost of a train ticket from Chicago to Kissimmee was $385.00. Train tickets on this route are typically priced higher due to the distance covered. You have the best chances of scoring the cheapest ticket to Kissimmee if you book your train tickets at least 25 days in advance. Waiting to purchase until the day of your trip could end up costing you an extra $231.00.
Monthly average prices
Prices as travel date approaches
Planning ahead pays off when it comes to booking your train trip from Chicago to Kissimmee. By reserving your ticket on Wanderu at least 25 days before departure, you can save around $231.00. Don't miss out on these savings — book in advance!
Which train should you take from Chicago to Kissimmee?
Amtrak is the one and only train line which connects Chicago to Kissimmee. The schedule is relatively limited as the train only runs twice a day.
| Train | Daily Trips | Avg. Time | Avg. Price |
|---|---|---|---|
| Amtrak | 2 | 1d 17h 11m | $648.22 |
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 Kissimmee every day, as well as 2 trips on the weekends, with prices starting from $345.
Frequently Asked Questions
The distance between Chicago and Kissimmee is approximately 1002 miles, or 1612 kilometers. The average train journey between these two cities takes 41 hours and 11 minutes, although the absolute fastest you could get there is 39 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.
On a weekly basis, the greatest number of passengers tend to travel by trains from Chicago to Kissimmee on Sunday. Tickets for Sunday tend to also be the most expensive. For savvy travelers looking for cheaper priced tickets search for travel departing on Wednesday. Wednesday 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 Kissimmee 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.
Kissimmee
Image credit: Unsplash
Image credit: Pixabay
Image credit: Pixabay
A small town in central Florida, Kissimmee is a popular destination for fans of amusement parks and other landmarks. The city is very close to many different amusement parks, including the world-famous Walt Disney World Resort, which is why Kissimmee is a popular place to stay for park-goers. Other surrounding amusement parks to check out include the Universal Orlando Resort and the SeaWorld Parks & Resorts. If amusement parks are not your thing, you could also check out the local Titanic: The Artifact Exhibition, which showcases artifacts related to the ill-fated ship. And don't miss the Bok Tower Gardens, which offers an amazing green space for picnics.
If you wish to try the best dishes in town, try Del Frisco's Double Eagle Steak House, which offers some of the best authentically American steaks in town, coupled with fine wine. Another great choice is Jaleo, run by the award-winning chef José Andrés.
The principal train station in Kissimmee is the Grand Central Station, which serves Amtrak Silver Service trains. The main bus station is located at 1979 E Osceola Pkwy. Both bus and train service connect Kissimmee to cities including Orlando, Miami, Atlanta, and more.
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 Kissimmee?
Main arrival station: Grand Central Station - 111 E Dakin Ave
The Kissimmee Amtrak Station is located at 111 E Dakin Ave in Kissimmee, Florida. The station is served by Amtrak's Silver Star and Silver Meteor trains, plus SunRail, the area's commuter rail system. The station has a waiting room and restrooms but no free WiFi. Luckily, you can connect to WiFi once on the train! Because the station is in downtown Kissimmee, many coffee shops, bars, and restaurants are within a short walk.
Train stations in Kissimmee:
Grand Central Station - 111 E Dakin Ave
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