Next train departures

Next departures for Winona to Chicago on October 16
Vehicle type	Departure time	Departure location	Trip duration	Arrival time	Arrival location	Recommended
Train Wi‑Fi Toilet Power outlets	1:41pm	Winona Station	5h 50m	7:31pm	Chicago (Union Station), IL	Cheapest
Train Wi‑Fi Toilet Power outlets	11:01am	Winona Station	5h 44m	4:45pm	Chicago (Union Station), IL	Fastest
Train Wi‑Fi Toilet Power outlets	11:01am	Winona Station	5h 44m	4:45pm	Chicago (Union Station), IL	No tags
Train Wi‑Fi Toilet Power outlets	11:01am	Winona Station	5h 44m	4:45pm	Chicago (Union Station), IL	No tags
Train Wi‑Fi Toilet Power outlets	11:01am	Winona Station	8h 30m	7:31pm	Chicago (Union Station), IL	No tags
Train Wi‑Fi Toilet Power outlets	11:01am	Winona Station	8h 30m	7:31pm	Chicago (Union Station), IL	No tags
Train Wi‑Fi Toilet Power outlets	11:01am	Winona Station	8h 30m	7:31pm	Chicago (Union Station), IL	No tags
Train Wi‑Fi Toilet Power outlets	1:41pm	Winona Station	7h 33m	9:14pm	Chicago (Union Station), IL	No tags

Next departures for Winona to Chicago on October 17
Vehicle type	Departure time	Departure location	Trip duration	Arrival time	Arrival location	Recommended
Train Wi‑Fi Toilet Power outlets	1:41pm	Winona Station	5h 50m	7:31pm	Chicago (Union Station), IL	Cheapest
Train Wi‑Fi Toilet Power outlets	11:01am	Winona Station	5h 44m	4:45pm	Chicago (Union Station), IL	Fastest
Train Wi‑Fi Toilet Power outlets	11:01am	Winona Station	5h 44m	4:45pm	Chicago (Union Station), IL	No tags
Train Wi‑Fi Toilet Power outlets	11:01am	Winona Station	8h 30m	7:31pm	Chicago (Union Station), IL	No tags
Train Wi‑Fi Toilet Power outlets	11:01am	Winona Station	8h 30m	7:31pm	Chicago (Union Station), IL	No tags
Train Wi‑Fi Toilet Power outlets	1:41pm	Winona Station	7h 33m	9:14pm	Chicago (Union Station), IL	No tags

Next departures for Winona to Chicago on October 18
Vehicle type	Departure time	Departure location	Trip duration	Arrival time	Arrival location	Recommended
Train Wi‑Fi Toilet Power outlets	11:01am	Winona Station	5h 44m	4:45pm	Chicago (Union Station), IL	CheapestFastest
Train Wi‑Fi Toilet Power outlets	11:01am	Winona Station	5h 44m	4:45pm	Chicago (Union Station), IL	No tags
Train Wi‑Fi Toilet Power outlets	1:41pm	Winona Station	5h 50m	7:31pm	Chicago (Union Station), IL	No tags
Train Wi‑Fi Toilet Power outlets	11:01am	Winona Station	8h 30m	7:31pm	Chicago (Union Station), IL	No tags
Train Wi‑Fi Toilet Power outlets	11:01am	Winona Station	8h 30m	7:31pm	Chicago (Union Station), IL	No tags
Train Wi‑Fi Toilet Power outlets	1:41pm	Winona Station	7h 33m	9:14pm	Chicago (Union Station), IL	No tags

Next departures for Winona to Chicago on October 19
Vehicle type	Departure time	Departure location	Trip duration	Arrival time	Arrival location	Recommended
Train Wi‑Fi Toilet Power outlets	1:41pm	Winona Station	5h 50m	7:31pm	Chicago (Union Station), IL	Cheapest
Train Wi‑Fi Toilet Power outlets	11:01am	Winona Station	5h 44m	4:45pm	Chicago (Union Station), IL	Fastest
Train Wi‑Fi Toilet Power outlets	11:01am	Winona Station	5h 44m	4:45pm	Chicago (Union Station), IL	No tags
Train Wi‑Fi Toilet Power outlets	11:01am	Winona Station	8h 30m	7:31pm	Chicago (Union Station), IL	No tags
Train Wi‑Fi Toilet Power outlets	11:01am	Winona Station	8h 30m	7:31pm	Chicago (Union Station), IL	No tags
Train Wi‑Fi Toilet Power outlets	1:41pm	Winona Station	7h 33m	9:14pm	Chicago (Union Station), IL	No tags

Next departures for Winona to Chicago on October 20
Vehicle type	Departure time	Departure location	Trip duration	Arrival time	Arrival location	Recommended
Train Wi‑Fi Toilet Power outlets	1:41pm	Winona Station	5h 50m	7:31pm	Chicago (Union Station), IL	Cheapest
Train Wi‑Fi Toilet Power outlets	11:01am	Winona Station	5h 44m	4:45pm	Chicago (Union Station), IL	Fastest
Train Wi‑Fi Toilet Power outlets	11:01am	Winona Station	5h 44m	4:45pm	Chicago (Union Station), IL	No tags
Train Wi‑Fi Toilet Power outlets	11:01am	Winona Station	8h 30m	7:31pm	Chicago (Union Station), IL	No tags
Train Wi‑Fi Toilet Power outlets	11:01am	Winona Station	8h 30m	7:31pm	Chicago (Union Station), IL	No tags
Train Wi‑Fi Toilet Power outlets	1:41pm	Winona Station	7h 33m	9:14pm	Chicago (Union Station), IL	No tags

Next departures for Winona to Chicago on October 21
Vehicle type	Departure time	Departure location	Trip duration	Arrival time	Arrival location	Recommended
Train Wi‑Fi Toilet Power outlets	1:41pm	Winona Station	5h 50m	7:31pm	Chicago (Union Station), IL	Cheapest
Train Wi‑Fi Toilet Power outlets	11:01am	Winona Station	5h 44m	4:45pm	Chicago (Union Station), IL	Fastest
Train Wi‑Fi Toilet Power outlets	11:01am	Winona Station	5h 44m	4:45pm	Chicago (Union Station), IL	No tags
Train Wi‑Fi Toilet Power outlets	11:01am	Winona Station	5h 44m	4:45pm	Chicago (Union Station), IL	No tags
Train Wi‑Fi Toilet Power outlets	11:01am	Winona Station	8h 30m	7:31pm	Chicago (Union Station), IL	No tags
Train Wi‑Fi Toilet Power outlets	11:01am	Winona Station	8h 30m	7:31pm	Chicago (Union Station), IL	No tags
Train Wi‑Fi Toilet Power outlets	11:01am	Winona Station	8h 30m	7:31pm	Chicago (Union Station), IL	No tags
Train Wi‑Fi Toilet Power outlets	1:41pm	Winona Station	7h 33m	9:14pm	Chicago (Union Station), IL	No tags

Next departures for Winona to Chicago on October 22
Vehicle type	Departure time	Departure location	Trip duration	Arrival time	Arrival location	Recommended
Train Wi‑Fi Toilet Power outlets	11:01am	Winona Station	5h 44m	4:45pm	Chicago (Union Station), IL	CheapestFastest
Train Wi‑Fi Toilet Power outlets	11:01am	Winona Station	5h 44m	4:45pm	Chicago (Union Station), IL	No tags
Train Wi‑Fi Toilet Power outlets	1:41pm	Winona Station	5h 50m	7:31pm	Chicago (Union Station), IL	No tags
Train Wi‑Fi Toilet Power outlets	11:01am	Winona Station	8h 30m	7:31pm	Chicago (Union Station), IL	No tags
Train Wi‑Fi Toilet Power outlets	11:01am	Winona Station	8h 30m	7:31pm	Chicago (Union Station), IL	No tags
Train Wi‑Fi Toilet Power outlets	1:41pm	Winona Station	7h 33m	9:14pm	Chicago (Union Station), IL	No tags

Last refresh of the prices: Today at 8:03 AM CDT.

Compare 2 ways to go from Winona to Chicago

We recommend taking the train

Among the sustainable travel choices, the Train stands out as a good way to reach Chicago. The journey takes about 5 hours 50 minutes, and with fares starting at just $57, it presents an excellent value for a comfortable ride.

3train per day

5h 50mAverage Duration

405 kmDistance

37kgCO₂ emissions

	Average Price	Average Duration	CO₂ emissions	Actions
Bus	Average Price$268 - $268	Average Duration15h 45m	CO₂ emissions 10kg CO₂e
Train	Average Price$57 - $968	Average Duration5h 50m	CO₂ emissions 37kg CO₂e

Train companies

Amtrak

4.1/56,572 reviews

Staff4.7

Timeliness3.8

Cleanliness4.5

Wi‑Fi3.6

Based on 6572 reviews, the company was rated 4.1 stars on Busbud. Travellers were especially satisfied with the seats and the ticket access but often complained with the Wi‑Fi. Amtrak ticket prices on this trip start at $57

US train companies:Amtrak, Amtrak Acela, Brightline

Frequently asked questions about travelling from Winona, MN to Chicago by train

Please note that schedules, routes, or operator details shown here may be updated or vary at the time of your trip.

How much is the train ticket from Winona to Chicago?
The cheapest train tickets from Winona to Chicago start at $57. The average price for this train route is around $103. Busbud recommends booking your tickets in advance to increase your chances of getting the lowest possible price.
How long is the train ride from Winona to Chicago?
The average train trip from Winona to Chicago takes 5h 50m and covers 405 km. The quickest train gets you there in 5h 40m and is operated by Amtrak.
Which train operators serve the Winona to Chicago route?
Several major train operators serve this route, with 3 trains available per day.
What are the earliest and latest departure times for the train from Winona to Chicago?
The earliest train from Winona to Chicago departs at 11:01am. The latest train departs at 1:41pm.

Find cheapest prices for trains

Price is for a one-way ticket for one passenger and based on past searches.

Best price found

10-13

$53

10-14

$65

Today

$121

10-16

$98

10-17

$53

10-18

$150

10-19

$53

10-20

$53

The cheapest trip from Winona, MN to Chicago was searched and found on Oct 13, 2026 with a price of $53

To save money and be sure you have the best seat, it's a good idea to buy your train tickets from Winona, MN to Chicago, as early as possible.

You can expect to pay from $53 to $934 for a train ticket from Winona, MN to Chicago based on the last 2 days. You can expect to find the cheapest price for the trip at $53 which is on 2026-10-17.

What's the cheapest way to go from Winona, MN to Chicago?

The Train is the cheapest travel choice for this destination

Vehicle Type	Travel time	Avg Price	Daily Departures
Vehicle TypeBus	Travel time15h 45m	Avg Price$268	Daily Departures1
Vehicle TypeTrain	Travel time5h 50m	Avg Price$103	Daily Departures3

The best way to travel between Winona, MN and Chicago is by train. By choosing the train, you'll get to save some money as you travel to your destination, as ticket prices cost $103 on average. If you're on a budget, you'll find cheap tickets from $57. If you're looking for the fastest way to get to Chicago, choose the train, as it will take you from Winona, MN to Chicago in about 5h 50m —that's the fastest way to get there!