Next bus departures
| Operated by | Vehicle type | Departure time | Departure location | Trip duration | Arrival time | Arrival location | Recommended | Price and booking link |
|---|---|---|---|---|---|---|---|---|
 | Bus | Winona St Uni | Chicago (Bus Station) | CheapestFastest |
Last refresh of the prices: Yesterday at 9:17 PM CST.
Compare 2 ways to go from Winona to Chicago
Among the sustainable travel choices, the train stands out as the good way to reach Chicago. The journey takes about 5 hours 44 minutes and with fares starting at just $39, it presents an excellent value for a comfortable ride.
Compare bus companies
Founded in 1919, Jefferson Lines provides bus services across the Midwest in the US. Their buses have WiFi, USB plugs, bathrooms, reclining seats, reading lights and GPS tracking. Tickets are non-refundable, but you can change the date by paying a fee. Known for their affordable prices and convenient schedules, if you're looking to travel in the Midwest, Jefferson Lines is the way to go.
Frequently asked questions about traveling from Winona, MN to Chicago by bus
Find cheapest prices for buses
Price is for a one-way ticket for one passenger and based on past searches.
The cheapest trip from Winona, MN to Chicago was searched and found on Nov 17, 2025 with a price of $179To save money and be sure you have the best seat, it's a good idea to buy your bus tickets from Winona, MN to Chicago, as early as possible.
You can expect to pay from $179 to $197 for a bus ticket from Winona, MN to Chicago based on the last 2 days. You can expect to find the cheapest price for the trip at $197 which is on 2025-11-21.
