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One passenger / one way
- This trip is recommended because it is the: Cheapest + FastestDeparture time: June 16 atDeparture city: ChicagoDeparture location: Chicago (Union Station), ILArrival time: June 18 atDestination city: KissimmeeDestination location: SunRail StationOperated by: Amtrak
Vehicle: TrainDuration: - Departure time: June 16 atDeparture city: ChicagoDeparture location: Chicago (Union Station), ILArrival time: June 18 atDestination city: KissimmeeDestination location: SunRail StationOperated by: AmtrakVehicle: TrainDuration:
- Departure time: June 16 atDeparture city: ChicagoDeparture location: Chicago (Union Station), ILArrival time: June 18 atDestination city: KissimmeeDestination location: SunRail StationOperated by: AmtrakVehicle: TrainDuration:
Last refresh of the prices: Last Monday at 8:13 AM CDT.
Prices and availability are subject to change.
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Compare 2 ways to go from Chicago to Kissimmee
Busbud recommends taking the bus from Chicago to KissimmeeAmong the sustainable travel choices, the bus stands out as a good way to reach Kissimmee. The journey takes about 1 day, 6 hours 5 minutes, and with fares starting at just US$92, it presents an excellent value for a comfortable ride.
Train Chicago to Kissimmee: 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 WiFi. Amtrak ticket prices on this trip start at US$228.00
Chicago to Kissimmee Train
Busbud shows you the best train ticket fares and train schedules so you can easily plan and book a trip by train from Chicago to Kissimmee.
We make sure you can find a train service from Chicago to Kissimmee from the most reliable train companies operating this trip.
Whether it is train tickets or first class train tickets going to Kissimmee from Chicago, we help you find what you're looking for based on how much of a budget you have.
Frequently asked questions on the trip Chicago - Kissimmee
How much does a cheap train ticket from Chicago to Kissimmee cost?
The average train ticket price from Chicago to Kissimmee is US$414. The best way to find cheap train tickets from Chicago to Kissimmee 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 trip from Chicago to Kissimmee?
A train trip between Chicago and Kissimmee is around 1d 15h, although the fastest train will take about 1d 15h. This is the time it takes to travel the 1611 km that separates the two cities.
How many daily trains are there between Chicago and Kissimmee?
The number of trains from Chicago to Kissimmee can differ depending on the day of the week. On average, there are 2. Some trains are direct while others include transferring trains. Simplify your train trip from Chicago to Kissimmee 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 Chicago to Kissimmee was searched and found on Jun 14, 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 Chicago to Kissimmee, as early as possible.
You can expect to pay from US$270 to US$2,419 for a train ticket from Chicago to Kissimmee based on the last 2 days. You can expect to find the cheapest price for the trip at US$328 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 Chicago and Kissimmee is also a great way to travel to arrive in the city centre and save more time for your stay in Kissimmee.
Regional train? High-speed train? Whichever train to Kissimmee you take, you’ll help reduce the environmental impact and carbon footprint of your trip. As you watch the landscapes unfold before your eyes, you can tell yourself that with this choice, you are making sure they remain protected.
By choosing the train between Chicago and Kissimmee, you emit up to 30 times less CO2 than for the same journey made by plane or car!
Make a music playlist for your train ride from Chicago to Kissimmee, and enjoy the scenery to tunes from your own personal soundtrack.
Did you know?
The first high-speed train line was inaugurated in 1964, in Japan, to connect Tokyo with Osaka. It was during the Olympics that the first passengers travelled aboard the Shinkansen at a speed of 210 km / h.
The magnetic levitation train (Maglev for short) is currently the fastest train in the world. With a speed of 603 km/ h, it is closely followed by the French high-speed train (574.8 km / h) which remains in 2020, the fastest train to date.
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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