IL → MN · about 251 miles
Chicago to Winona train schedule
Amtrak runs 21 direct trains a week from Chicago to Winona. The fastest takes 5 hours 29 minutes; the first train leaves at 11:10 AM and the last at 3:05 PM.
Timetable data from · No schedule changes since at least
- Trains a week
- 21
- Fastest trip
- 5h 29m
- First train
- 11:10 AM
- Last train
- 3:05 PM
Timetable
Every train leaves from Chicago Union Station and arrives at Winona. 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 |
|---|---|---|---|---|
| 11:10 AM | 4:45 PM | 5h 35m | Daily | Amtrak Full timetable |
| 3:05 PM | 8:34 PM | 5h 29m | Daily | Amtrak Full timetable |
Route map
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Where to board in Chicago Where you get off in Winona The route of the busiest trip
Where to catch the train in Chicago
Where the train stops in Winona
Return trip: Winona to Chicago
Questions
How long is the train from Chicago to Winona?
The fastest direct train takes 5 hours 29 minutes; the typical trip is 5 hours 29 minutes.
What time is the first train from Chicago to Winona?
The earliest departure is at 11:10 AM (Daily) and the last at 3:05 PM (Daily).
Which rail companies go from Chicago to Winona?
Amtrak runs direct trains on this route.
Where do I catch the train in Chicago?
Trains to Winona leave from Chicago Union Station.