Previously seen trips

Next departures for Chicago to Winona on August 31
Vehicle type	Departure time	Departure location	Trip duration	Arrival time	Arrival location
Train	6:10am	Chicago (Union Station), IL	10h 35m	4:45pm	Winona Station
Train	8:25am	Chicago (Union Station), IL	8h 20m	4:45pm	Winona Station
Train	11:10am	Chicago (Union Station), IL	5h 35m	4:45pm	Winona Station
Train	3:05pm	Chicago (Union Station), IL	5h 29m	8:34pm	Winona Station
Train	6:10am	Chicago (Union Station), IL	10h 35m	4:45pm	Winona Station

Compare 2 ways to go from Chicago to Winona

We recommend taking the train

Among the sustainable travel choices, the Train stands out as a good way to reach Winona. The journey takes about 5 hours 35 minutes, and with fares starting at just ZAR 638, it presents an excellent value for a comfortable ride.

3train per day

5h 35mAverage Duration

405 kmDistance

37kgCO₂ emissions

	Average Price	Average Duration	CO₂ emissions	Actions
Bus	Average PriceZAR 3,045 - ZAR 3,147	Average Duration16h 45m	CO₂ emissions 10kg CO₂e
Train	Average PriceZAR 638 - ZAR 12,442	Average Duration5h 35m	CO₂ emissions 37kg CO₂e

Train companies

Amtrak

4.1/56,473 reviews

Staff4.7

Timeliness3.8

Cleanliness4.5

Wi‑Fi3.6

Based on 6473 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 ZAR 638

US train companies:Amtrak, Amtrak Acela, Brightline

Frequently asked questions about travelling from Chicago to Winona, MN 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 Chicago to Winona?
The cheapest train tickets from Chicago to Winona start at ZAR 638. The average price for this train route is around ZAR 1,582. Busbud recommends booking your tickets in advance to increase your chances of getting the lowest possible price.
How long is the train ride from Chicago to Winona?
The average train trip from Chicago to Winona takes 5h 35m and covers 405 km. The quickest train gets you there in 5h 29m and is operated by Amtrak.
Which train operators serve the Chicago to Winona 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 Chicago to Winona?
The earliest train from Chicago to Winona departs at 6:10am. The latest train departs at 3:05pm.

Find cheapest prices for trains

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

Best price found

08-28

ZAR 2,470

08-29

ZAR 1,393

Today

ZAR 2,470

08-31

ZAR 1,708

09-01

ZAR 597

09-02

ZAR 730

09-03

ZAR 1,376

09-04

ZAR 1,111

The cheapest trip from Chicago to Winona, MN was searched and found on Sep 1, 2026 with a price of ZAR 597

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

You can expect to pay from ZAR 597 to ZAR 8,438 for a train ticket from Chicago to Winona, MN based on the last 2 days. You can expect to find the cheapest price for the trip at ZAR 597 which is on 2026-09-01.

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

The Train is the cheapest travel choice for this destination

Vehicle Type	Travel time	Avg Price	Daily Departures
Vehicle TypeBus	Travel time16h 45m	Avg PriceZAR 3,045	Daily Departures1
Vehicle TypeTrain	Travel time5h 35m	Avg PriceZAR 1,582	Daily Departures3

The best way to travel between Chicago and Winona, MN is by train. By choosing the train, you'll get to save some money as you travel to your destination, as ticket prices cost ZAR 1,582 on average. If you're on a budget, you'll find cheap tickets from ZAR 638. If you're looking for the fastest way to get to Winona, MN, choose the train, as it will take you from Chicago to Winona, MN in about 5h 35m —that's the fastest way to get there!