FL → IL · about 983 miles
Winter Park to Chicago train schedule
Amtrak runs 7 direct trains a week from Winter Park to Chicago. The fastest takes 38 hours 38 minutes; every train leaves at 7:07 PM.
Timetable data from · No schedule changes since at least
- Trains a week
- 7
- Fastest trip
- 38h 38m
- Leaves at
- 7:07 PM
Timetable
Every train leaves from Winter Park 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 |
|---|---|---|---|---|
| 7:07 PM | 8:45 AM +2 day | 38h 38m | Daily | Amtrak Full timetable |
| 7:07 PM | 9:45 AM +2 day | 39h 38m | Sat | Amtrak Full timetable |
Route map
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Where to board in Winter Park Where you get off in Chicago The route of the busiest trip
Where to catch the train in Winter Park
- Winter Park Amtrak Station Map of Winter Park Amtrak Station (Google Maps)
Where the train stops in Chicago
Return trip: Chicago to Winter Park
Questions
How long is the train from Winter Park to Chicago?
The fastest direct train takes 38 hours 38 minutes; the typical trip is 38 hours 38 minutes.
What time is the first train from Winter Park to Chicago?
Every departure is at 7:07 PM (Daily).
Which rail companies go from Winter Park to Chicago?
Amtrak runs direct trains on this route.
Where do I catch the train in Winter Park?
Trains to Chicago leave from Winter Park Amtrak Station.