Next departures
| Operated by | Vehicle type | Departure time | Departure location | Trip duration | Arrival time | Arrival location | Recommended | Price and booking link |
|---|---|---|---|---|---|---|---|---|
 | Chicago (Union Station), IL | SunRail Station | CheapestFastest | |||||
| Chicago (Union Station), IL | SunRail Station | No tags | |||||
| Chicago (Union Station), IL | SunRail Station | No tags | |||||
| Chicago (Union Station), IL | SunRail Station | No tags |
Last refresh of the prices: Last Sunday at 2:18 AM CST.
Compare 2 ways to go from Chicago to Kissimmee
Among the sustainable travel choices, the bus stands out as a good way to reach Kissimmee. The journey takes about 1 day, 5 hours 35 minutes, and with fares starting at just $176, it presents an excellent value for a comfortable ride.
Train companies
Based on 5620 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 $338
Frequently asked questions about travelling from Chicago to Kissimmee by train
Please note that schedules, routes, or operator details shown here may be updated or vary at the time of your trip.
How much is the train ticket from Chicago to Kissimmee?
The cheapest train tickets from Chicago to Kissimmee start at $338. The average price for this train route is around $636. Busbud recommends booking your tickets in advance to increase your chances of getting the lowest possible price.
How long is the train ride from Chicago to Kissimmee?
The average train trip from Chicago to Kissimmee takes 1d 14h and covers 1613 km. The quickest train gets you there in 1d 14h and is operated by Amtrak.
Which train operators serve the Chicago to Kissimmee route?
Several major train operators serve this route, with 2 trains available per day.
What are the earliest and latest departure times for the train from Chicago to Kissimmee?
The earliest train from Chicago to Kissimmee departs at 6:40pm. The latest train departs at 6:40pm.
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 Dec 5, 2025 with a price of $325To 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 $325 to $2,620 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 $325 which is on 2025-12-05.
