Next train departures
| Operated by | Vehicle type | Departure time | Departure location | Trip duration | Arrival time | Arrival location | Recommended | Price and booking link |
|---|---|---|---|---|---|---|---|---|
 | Train | SunRail Station | Chicago (Union Station), IL | Cheapest | ||||
| Train | SunRail Station | Chicago (Union Station), IL | Fastest | ||||
| Train | SunRail Station | Chicago (Union Station), IL | No tags | ||||
| Train | SunRail Station | Chicago (Union Station), IL | No tags | ||||
| Train | SunRail Station | Chicago (Union Station), IL | No tags |
Last refresh of the prices: Yesterday at 9:23 AM EST.
Compare 2 ways to go from Kissimmee to Chicago
Among the sustainable travel choices, the bus stands out as a good way to reach Chicago. The journey takes about 1 day, 9 hours 10 minutes, and with fares starting at just $161, it presents an excellent value for a comfortable ride.
Train companies
Based on 5621 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 $190
Frequently asked questions about travelling from Kissimmee to Chicago 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 Kissimmee to Chicago?
The cheapest train tickets from Kissimmee to Chicago start at $190. The average price for this train route is around $626. Busbud recommends booking your tickets in advance to increase your chances of getting the lowest possible price.
How long is the train ride from Kissimmee to Chicago?
The average train trip from Kissimmee to Chicago takes 1d 20h and covers 1613 km. The quickest train gets you there in 1d 15h and is operated by Amtrak.
Which train operators serve the Kissimmee to Chicago route?
Several major train operators serve this route, with 3 trains available per day.
What are the earliest and latest departure times for the train from Kissimmee to Chicago?
The earliest train from Kissimmee to Chicago departs at 12:57pm. The latest train departs at 6:10pm.
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 Dec 2, 2025 with a price of $324To 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 $324 to $3,424 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 $422 which is on 2025-12-04.
