Cheap train tickets from Chicago to Kissimmee

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Trip Summary

There are usually 2 daily train trips available from Chicago to Kissimmee. Traveling by train from Chicago to Kissimmee usually takes 1 day, 16 hours, and 44 minutes, but the fastest Amtrak Floridian train can make the trip in 1 day, 14 hours, and 58 minutes.

Distance: 1002 mi (1612 km)
Fastest train: 38h 58m
Lowest price: MX$6,417.06
Trains per day: 1
Most frequent service: Amtrak
Train lines: 2

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Chicago to Kissimmee Train Schedule

No preview is currently available. Please try another date or search the full schedule.

There are several train options that can take you from Chicago to Kissimmee:

See more details

What 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 MX$6,417. 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 5 days prior to the travel date. You’ll likely pay around MX$4,784.65 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 MX$3,171 and MX$5,573. 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 MX$6,530. 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 MX$11,089 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 5 days ahead of time, you can save about MX$4,784.65 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. Amtrak usually has more trains scheduled, with 2 trips per day. That said, it's still worth comparing the prices and trip durations:

Train	Daily Trips	Avg. Time	Avg. Price
Amtrak	2	42h 13m	MX$8,171.43
Amtrak Floridian	1	38h 58m	MX$6,826.10

Amtrak Floridian train tickets from Chicago to Kissimmee start from MX$3,621.32, and on average cost MX$6,826.10. Daily, Amtrak Floridian runs one schedule 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 1 day, 14 hours, and 58 minutes.

Frequently asked questions about traveling by train from Chicago to Kissimmee

Yes, there are trains that can take you the entire way from Chicago to Kissimmee. However, there are also some trips on this route that require you to board another vehicle, such as a bus or a shuttle, during your journey. This is worth paying attention to as you book your trip, since a direct train may be preferable for its speed and convenience.

Trains leave the station in Chicago twice a day, so there are a couple of options depending on your preferred travel time. One of these is a direct train, which will typically get you to Kissimmee faster. While it might still have stops along the way, you will not need to switch trains during your trip. You can also take a train for your return trip from Kissimmee to Chicago.

Trains per day

Direct trains

The distance between Chicago and Kissimmee is approximately 1,002 miles. The average train journey between these two cities takes 1 day, 16 hours, and 44 minutes, although the absolute fastest you could get there is 1 day, 14 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 5:55 PM while the last train of the day leaves at 6:40 PM. 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 Thursday. 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 Monday instead, as it tends to be the least crowded day of the week.

Busiest

Thursday

Least crowded

Monday

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 in nearby Lake Wales, 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 Kissimmee 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

Grand Central Station - 111 E Dakin Ave -{"city":"Kissimmee","country":"US","postal":"34741","state":"FL","street1":"111 E Dakin Ave"} - KISAMT-0

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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