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One passenger / one way
- This trip is recommended because it is: Cheapest + FastestDeparture time: June 16 atDeparture city: KissimmeeDeparture location: SunRail StationArrival time: June 18 atDestination city: ChicagoDestination location: Chicago (Union Station), ILOperated by: Amtrak
Vehicle: TrainDuration: - Departure time: June 16 atDeparture city: KissimmeeDeparture location: SunRail StationArrival time: June 18 atDestination city: ChicagoDestination location: Chicago (Union Station), ILOperated by: AmtrakVehicle: TrainDuration:
- Departure time: June 16 atDeparture city: KissimmeeDeparture location: SunRail StationArrival time: June 18 atDestination city: ChicagoDestination location: Chicago (Union Station), ILOperated by: AmtrakVehicle: TrainDuration:
- Departure time: June 16 atDeparture city: KissimmeeDeparture location: SunRail StationArrival time: June 18 atDestination city: ChicagoDestination location: Chicago (Union Station), ILOperated by: AmtrakVehicle: TrainDuration:
- Departure time: June 16 atDeparture city: KissimmeeDeparture location: SunRail StationArrival time: June 18 atDestination city: ChicagoDestination location: Chicago (Union Station), ILOperated by: AmtrakVehicle: TrainDuration:
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Compare 2 ways to go from Kissimmee to Chicago.
Busbud recommends taking the bus from Kissimmee to ChicagoAmong the sustainable travel choices, the bus stands out as the good way to reach Chicago. The journey takes about 1 day, 4 hours 40 minutes and with fares starting at just $128, it presents an excellent value for a comfortable ride.
Train Kissimmee to Chicago: Trip Overview
Please note, this information is subject to change.
Train Companies
Based on 5207 reviews, the company was rated 4.1 stars on Busbud. Travelers were especially satisfied with the seats and the ticket access but often complained with the wifi. Amtrak ticket prices on this trip start at $281.00
Kissimmee to Chicago Train
Busbud shows you the best train ticket fares and train schedules so you can easily plan and book a trip by train from Kissimmee to Chicago.
Train service from Kissimmee to Chicago will be provided by the most trusted companies.
Whether it is train tickets or first class train tickets going to Chicago from Kissimmee, we help you find what you're looking for based on how much of a budget you have.
Frequently asked questions for your trip Kissimmee - Chicago
Find cheapest prices for trains
Price is for a one-way ticket for one passenger and based on past searches.
The cheapest trip from Kissimmee to Chicago was searched and found on Jun 13, 2025 with a price of $270To save money and be sure you have the best seat, it's a good idea to buy your train tickets from Kissimmee to Chicago, as early as possible.
You can expect to pay from $270 to $2,977 for a train ticket from Kissimmee to Chicago based on the last 2 days. You can expect to find the cheapest price for the trip at $398 which is on 2025-06-17.
About Train Travel
Train Travel Tips
Do you like to go fast? With high-speed trains going faster than 300 km/h on certain routes, the time will fly by. Taking a train between Kissimmee and Chicago is also a great way to travel to arrive in the city centre and save more time for your stay in Chicago.
No matter if you plan to take a regional or high-speed train to Chicago, the planet will thank you. You’ll help to protect the beautiful landscapes that will unfold before your very eyes.
By choosing the train between Kissimmee and Chicago, you emit up to 30 times less CO2 than for the same journey made by plane or car!
Create your own real life musical score by curating a personalized train travel playlist - the perfect accompaniment to your bus ride from Kissimmee to Chicago.
Did you know?
Railway companies played a major role as early as 1883 in the use of time zones as we know them today.
You can find dogs as passengers on the trains of Moscow, where there is a large number of stray dogs. Over time, the dogs have learned the inner workings of the rail system and it is not uncommon to find one traveling between the city and the suburbs.
Some trains in Sweden can recover more than a fifth of the energy they use by braking. This is especially true with ore trains as they descend from Narvik to Kiruna.
Top Traveled Train Routes
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