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One passenger / one way
- This trip is recommended because it is the: Cheapest + FastestDeparture time: 16 June atDeparture city: KissimmeeDeparture location: SunRail StationArrival time: 18 June atDestination city: ChicagoDestination location: Chicago (Union Station), ILOperated by: Amtrak
Vehicle: TrainDuration: - Departure time: 16 June atDeparture city: KissimmeeDeparture location: SunRail StationArrival time: 18 June atDestination city: ChicagoDestination location: Chicago (Union Station), ILOperated by: AmtrakVehicle: TrainDuration:
- Departure time: 16 June atDeparture city: KissimmeeDeparture location: SunRail StationArrival time: 18 June atDestination city: ChicagoDestination location: Chicago (Union Station), ILOperated by: AmtrakVehicle: TrainDuration:
- Departure time: 16 June atDeparture city: KissimmeeDeparture location: SunRail StationArrival time: 18 June atDestination city: ChicagoDestination location: Chicago (Union Station), ILOperated by: AmtrakVehicle: TrainDuration:
- Departure time: 16 June atDeparture city: KissimmeeDeparture location: SunRail StationArrival time: 18 June atDestination city: ChicagoDestination location: Chicago (Union Station), ILOperated by: AmtrakVehicle: TrainDuration:
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Compare 2 ways to travel from Kissimmee to Chicago
Busbud recommends taking the bus from Kissimmee to ChicagoAmong the sustainable travel choices, the bus stands out as a good way to reach Chicago. The journey takes about 1 day, 4 hours 40 minutes and with fares starting at just US$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 5206 reviews, the company was rated 4.1 stars on Busbud. Travellers were especially satisfied with the seats and the ticket access but often complained with the Wi-Fi. Amtrak ticket prices on this trip start at US$281.00
Kissimmee to Chicago Train
Busbud shows you the best train ticket fares and train schedules so you can plan and book a trip by train easily from Kissimmee to Chicago.
Train services 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 on the trip Kissimmee - Chicago
How much does a cheap train ticket from Kissimmee to Chicago cost?
The average train ticket price from Kissimmee to Chicago is US$386. The best way to find cheap train tickets from Kissimmee to Chicago is to book your tickets as early as possible. Prices tend to rise as your travel date approaches, so book in advance to secure the best prices!
How long is the train trip from Kissimmee to Chicago?
A train trip between Kissimmee and Chicago is around 1d 20h, although the fastest train will take about 1d 15h. This is the time it takes to travel the 999 miles that separates the two cities.
How many daily train are there between Kissimmee and Chicago?
The number of trains from Kissimmee to Chicago can differ depending on the day of the week. On average, there are 3. Some trains are direct while others include transferring trains. Simplify your train trip from Kissimmee to Chicago by comparing and selecting the train that fits your travel style and budget on Busbud.
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 13 Jun 2025 with a price of US$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 US$270 to US$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 US$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 personalised train travel playlist – the perfect accompaniment for your journey 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 travelling 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 Travelled Train Routes
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