IL → FL · about 1,001 miles
Chicago to Kissimmee train schedule
Amtrak runs 7 direct trains a week from Chicago to Kissimmee. The fastest takes 38 hours 58 minutes; the first train leaves at 5:35 PM and the last at 6:40 PM.
Timetable data from · Schedule last changed
- Trains a week
- 7
- Fastest trip
- 38h 58m
- First train
- 5:35 PM
- Last train
- 6:40 PM
Timetable
Every train leaves from Chicago Union Station and arrives at Kissimmee Amtrak Station. Times are local to each stop. Timetables published by tds.ai, refreshed October 15, 2026. Schedules change, so check times when you book.
| Departs | Arrives | Duration | Days | Rail company |
|---|---|---|---|---|
| 5:35 PM New | 10:38 AM +2 day | 40h 03m | Sun | Amtrak Full timetable |
| 6:40 PM | 10:38 AM +2 day | 38h 58m | Daily | Amtrak Full timetable |
Route map
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Where to board in Chicago Where you get off in Kissimmee The route of the busiest trip
Where to catch the train in Chicago
Where the train stops in Kissimmee
Return trip: Kissimmee to Chicago
Questions
How long is the train from Chicago to Kissimmee?
The fastest direct train takes 38 hours 58 minutes; the typical trip is 38 hours 58 minutes.
What time is the first train from Chicago to Kissimmee?
The earliest departure is at 5:35 PM (Sun) and the last at 6:40 PM (Daily).
Which rail companies go from Chicago to Kissimmee?
Amtrak runs direct trains on this route.
Where do I catch the train in Chicago?
Trains to Kissimmee leave from Chicago Union Station.