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Winona to Chicago Union Station buses

Find Transport to Chicago Union Station

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Trip Overview

The bus between Winona and Chicago Union Station takes 9h 10m. The bus runs, on average, 6 times per week from Winona to Chicago Union Station. The journey time may be longer on weekends and holidays; use the search form on this page to search for a specific travel date.

9h 10m
Duration
321 mi
Distance
$91
Average price
6 times a week
Frequency

Winona to Chicago Union Station bus times

Buses run 6 times a week between Winona and Chicago Union Station. The service departs Winona at 1:30 PM in the afternoon, which arrives into Chicago Union Station at 21:40:00. All services require a transfer at Milwaukee and take an average of 9h 10m. The schedules shown below are for the next available departures.

Departing Saturday, November 7, 2026

  •  → 

    Jefferson LinesGreyhound USA9h 10m • 1 change

Departing Sunday, November 8, 2026

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    Jefferson LinesGreyhound USA9h 10m • 1 change

Departing Monday, November 9, 2026

  •  → 

    Jefferson LinesGreyhound USA9h 10m • 1 change

Departing Tuesday, November 10, 2026

  •  → 

    Jefferson LinesGreyhound USA9h 10m • 1 change

Departing Wednesday, November 11, 2026

  •  → 

    Jefferson LinesGreyhound USA9h 10m • 1 change

Departing Thursday, November 12, 2026

  •  → 

    Jefferson LinesGreyhound USA9h 10m • 1 change

Frequently asked questions

Want to know about travelling from Winona to Chicago Union Station? We have put together a list of the most frequently asked questions from our users such as: What is the cheapest mode of transport? What is the quickest option? How much do tickets usually cost? and many more.

Map of how to get from Winona to Chicago Union Station.ExpandLaunch map view
  • Distance: 321.5 mi
  • Duration: 9h 10m

What companies run services between Winona, MN, USA and Chicago Union Station, IL, USA?

You can take a bus from Winona St. University to Chicago Union Station via Milwaukee, Milwaukee Intermodal Station, and Chicago Bus Station in around 7h 29m.

Operators