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 | |||||
| Chicago (Union Station), IL | SunRail Station | No tags |
Last refresh of the prices: Last Saturday at 3:41 AM CST.
Compare 2 ways to travel 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 R 2 121, it presents an excellent value for a comfortable ride.
Train Companies
Based on 5639 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 R 2 294
Frequently asked questions about travelling from Chicago to Kissimmee by train
Please note that timetables, routes, or operator details shown here may be updated or differ 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 from R 2 294. The average price for this train route is around R 7 554. Busbud recommends booking your tickets in advance for a better chance to secure the lowest possible price.
How long is the train journey from Chicago to Kissimmee?
The average train journey time from Chicago to Kissimmee is 1d 14h, covering a distance of 1613 km. The quickest train can get you there in 1d 14h and is operated by Amtrak.
Which train operators serve the Chicago to Kissimmee route?
Several major train operators run on 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 18:40. And the latest train departs at 18:40.
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 11 Dec 2025 with a price of R 4 668To 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 R 4 668 to R 43 807 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 R 4 668, which is on 2025-12-13.
