FL → IL · about 1,014 miles
Winter Haven to Chicago train schedule
Amtrak runs 7 direct trains a week from Winter Haven to Chicago. The fastest takes 42 hours 49 minutes; every train leaves at 2:56 PM.
Timetable data from · No schedule changes since at least
- Trains a week
- 7
- Fastest trip
- 42h 49m
- Leaves at
- 2:56 PM
Timetable
Every train leaves from Winter Haven 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 |
|---|---|---|---|---|
| 2:56 PM | 8:45 AM +2 day | 42h 49m | Daily | Amtrak Full timetable |
| 2:56 PM | 9:45 AM +2 day | 43h 49m | Sat | Amtrak Full timetable |
Route map
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Where to board in Winter Haven Where you get off in Chicago The route of the busiest trip
Where to catch the train in Winter Haven
Where the train stops in Chicago
Return trip: Chicago to Winter Haven
Questions
How long is the train from Winter Haven to Chicago?
The fastest direct train takes 42 hours 49 minutes; the typical trip is 42 hours 49 minutes.
What time is the first train from Winter Haven to Chicago?
Every departure is at 2:56 PM (Daily).
Which rail companies go from Winter Haven to Chicago?
Amtrak runs direct trains on this route.
Where do I catch the train in Winter Haven?
Trains to Chicago leave from Winter Haven Amtrak station.