FL → IL · about 1,001 miles
Kissimmee to Chicago train schedule
Amtrak runs 7 direct trains a week from Kissimmee to Chicago. The fastest takes 39 hours 35 minutes; every train leaves at 6:10 PM.
Timetable data from · No schedule changes since at least
- Trains a week
- 7
- Fastest trip
- 39h 35m
- Leaves at
- 6:10 PM
Timetable
Every train leaves from Kissimmee Amtrak Station and arrives at Chicago Union 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 |
|---|---|---|---|---|
| 6:10 PM | 8:45 AM +2 day | 39h 35m | Daily | Amtrak Full timetable |
| 6:10 PM | 9:45 AM +2 day | 40h 35m | Sat | Amtrak Full timetable |
Route map
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Where to board in Kissimmee Where you get off in Chicago The route of the busiest trip
Where to catch the train in Kissimmee
Where the train stops in Chicago
Return trip: Chicago to Kissimmee
Questions
How long is the train from Kissimmee to Chicago?
The fastest direct train takes 39 hours 35 minutes; the typical trip is 39 hours 35 minutes.
What time is the first train from Kissimmee to Chicago?
Every departure is at 6:10 PM (Daily).
Which rail companies go from Kissimmee to Chicago?
Amtrak runs direct trains on this route.
Where do I catch the train in Kissimmee?
Trains to Chicago leave from Kissimmee Amtrak Station.