MN → IL · about 251 miles
Winona to Chicago train schedule
Amtrak runs 21 direct trains a week from Winona to Chicago. The fastest takes 5 hours 40 minutes; the first train leaves at 11:01 AM and the last at 1:41 PM.
Timetable data from · No schedule changes since at least
- Trains a week
- 21
- Fastest trip
- 5h 40m
- First train
- 11:01 AM
- Last train
- 1:41 PM
Timetable
Every train leaves from Winona 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 |
|---|---|---|---|---|
| 11:01 AM | 4:45 PM | 5h 44m | Daily | Amtrak Full timetable |
| 1:41 PM | 7:21 PM | 5h 40m | Daily | Amtrak Full timetable |
Route map
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Where to board in Winona Where you get off in Chicago The route of the busiest trip
Where to catch the train in Winona
Where the train stops in Chicago
Return trip: Chicago to Winona
Questions
How long is the train from Winona to Chicago?
The fastest direct train takes 5 hours 40 minutes; the typical trip is 5 hours 44 minutes.
What time is the first train from Winona to Chicago?
The earliest departure is at 11:01 AM (Daily) and the last at 1:41 PM (Daily).
Which rail companies go from Winona to Chicago?
Amtrak runs direct trains on this route.
Where do I catch the train in Winona?
Trains to Chicago leave from Winona Amtrak station.