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Cheap train tickets from Chicago to Kissimmee
Find and compare the best ground travel options in one place.
Trip Summary
There are usually 2 daily train trips available from Chicago to Kissimmee. Traveling by train from Chicago to Kissimmee usually takes 40 hours and 47 minutes, but the fastest Amtrak Floridian train can make the trip in 38 hours and 58 minutes.
- Distance
- 1002 mi (1612 km)
- Fastest train
- 38h 58m
- Lowest price
- TRY 13,810.62
- Trains per day
- 1
- Most frequent service
- Amtrak
- Train lines
- 2
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Chicago to Kissimmee Train Schedule
There are several train options that can take you from Chicago to Kissimmee:
See more detailsWhat is the price of a train ticket from Chicago to Kissimmee?
In the last month, the average price of a train ticket from Chicago to Kissimmee was TRY 14,705.14. Considering the distance between Chicago and Kissimmee, tickets on this route are relatively expensive. Good news! You can find the cheapest tickets if you book your trip at least 17 days prior to the travel date. You’ll likely pay around TRY 10,012.45 more if you wait to book until the last minute.
Average train ticket prices from Chicago to Kissimmee by travel date
Over the next 30 days, a one-way train trip from Chicago to Kissimmee will cost between TRY 13,323 and TRY 16,007. Book in advance to secure the best price in the next few weeks.
Average train ticket prices from Chicago to Kissimmee by month
Ticket prices for the train from Chicago to Kissimmee often fluctuate based on the time of year. For the best prices on this route, book in September when the average ticket price is only TRY 16,836. If you're thinking of traveling from Chicago to Kissimmee during November, keep in mind that train ticket prices may be higher than usual, with an average price of TRY 30,305 during this time of year. The best way to score a cheap deal, even in November, is to book your trip well in advance.
Prices as travel date approaches
By booking your train trip from Chicago to Kissimmee on Wanderu at least 17 days ahead of time, you can save about TRY 10,012.45 on your ticket. Waiting until the last minute means missing out on these savings!
Which train should you take from Chicago to Kissimmee?
2 train services operate from Chicago to Kissimmee. However, each train line only offers one daily trip.
| Train | Daily Trips | Avg. Time | Avg. Price |
|---|---|---|---|
| Amtrak | 1 | 42h 9m | TRY 18,690.69 |
| Amtrak Floridian | 1 | 38h 58m | TRY 19,325.10 |
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 1 Amtrak trains from Chicago to Kissimmee every day, as well as 1 trips on the weekends, with prices starting from TRY 13,957.02.
Amtrak Floridian train tickets from Chicago to Kissimmee start from TRY 13,810.62, and on average cost TRY 19,325.10. Daily there are 1 Amtrak Floridian schedules to Kissimmee. Amtrak Floridian in Chicago leaves from Union Station. And in Kissimmee trains arrive at Grand Central Station - 111 E Dakin Ave.
From Chicago to Kissimmee train travel on Amtrak Floridian takes 38 hours and 58 minutes.
If you are looking to travel to Kissimmee on a weekend there is typically one Amtrak Floridian scheduled trip per day, which will cost TRY 13,810.62 for a one-way weekend reservation from Chicago.
Frequently asked questions about traveling by train from Chicago to Kissimmee
The distance between Chicago and Kissimmee is approximately 1002 miles, or 1612 kilometers. The average train journey between these two cities takes 40 hours and 47 minutes, although the absolute fastest you could get there is 38 hours and 58 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.
Distance (mi)
1002
Distance (km)
1612
The earliest train departs Chicago at 5:55pm while the last train of the day leaves at 6:40pm. To see all scheduled departure times, use the search function on this page to get the full schedule for your specific travel dates.
First train
5:55pm
Last train
6:40pm
Trains from Chicago to Kissimmee are the most crowded on Monday. Tickets also tend to be more expensive then. If you are looking for a great deal on your train tickets or just want extra room to stretch out, consider traveling on Sunday instead, as it tends to be the least crowded day of the week.
Busiest
Monday
Least crowded
Sunday
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
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?
Main departure station: Union Station
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:
- Union Station
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.
All train stations in Kissimmee:
- Grand Central Station - 111 E Dakin Ave
Need a return trip from Kissimmee to Chicago?
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