Next bus departures
| Operated by | Vehicle type | Departure time | Departure location | Trip duration | Arrival time | Arrival location | Recommended | Price and booking link |
|---|---|---|---|---|---|---|---|---|
Jefferson Lines + Jefferson Lines | Bus | Winona St Uni | Chicago (Bus Station) | CheapestFastest | ||||
 | Bus | Winona St Uni | Chicago (Bus Station) | No tags |
Last refresh of the prices: Yesterday at 9:05 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 7 hours 23 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
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 bus ticket from Winona to Chicago?
The cheapest bus tickets from Winona to Chicago start from $155. The average price for this route is around $184. Busbud recommends that you book your tickets in advance for a better chance to get the lowest possible price.
How long is the bus ride from Winona to Chicago?
The average bus trip duration from Winona to Chicago is 15h 45m, covering a distance of 252 miles (406 km). The quickest bus can get you there in 15h 45m and is operated by Jefferson Lines.
Which bus companies service the Winona to Chicago route?
Several major train operators operate on this route with 1 trains available per day.
What is the earliest and latest departure time for the bus from Winona to Chicago?
The earliest bus departs from Winona to Chicago at 1:45pm. And the latest bus departs at 5:10pm.
What are the CO₂ emissions for the bus trip from Winona to Chicago?
A bus trip from Winona to Chicago generates an estimated 10 kg of CO₂, making it a highly eco-friendly travel option and recommended mode of travel by Busbud.
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 Jan 20, 2026 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 $179 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 $179 which is on 2026-01-23.
