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Winona to Chicago Union Station buses

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Trip Overview

The bus between Winona and Chicago Union Station takes 7h 50m. There is at least one bus per day 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.

7h 50m
Duration
312 mi
Distance
$108
Average price
Once daily
Frequency

Winona to Chicago Union Station bus times

Buses run once daily between Winona and Chicago Union Station. The service departs Winona at 1:30 PM in the afternoon, which arrives into Chicago Union Station at 20:20:00. All services require a transfer at Madison and take an average of 7h 50m. The schedules shown below are for the next available departures.

Departing Thursday, November 12, 2026

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    Jefferson LinesRockland Coaches7h 50m • 1 change

Departing Friday, November 13, 2026

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    Jefferson LinesRockland Coaches7h 50m • 1 change

Departing Saturday, November 14, 2026

  •  → 

    Jefferson LinesRockland Coaches7h 50m • 1 change

Departing Sunday, November 15, 2026

  •  → 

    Jefferson LinesRockland Coaches7h 50m • 1 change

Departing Monday, November 16, 2026

  •  → 

    Jefferson LinesRockland Coaches7h 50m • 1 change

Departing Tuesday, November 17, 2026

  •  → 

    Jefferson LinesRockland Coaches7h 50m • 1 change

Departing Wednesday, November 18, 2026

  •  → 

    Jefferson LinesRockland Coaches7h 50m • 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: 311.9 mi
  • Duration: 7h 50m

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

You can take a bus from Winona St. University to W Jackson Blvd, after S Clinton St via Madison and 250 N. Lake St - Madison UW Campus in around 7h 56m.

Operators