Previously seen trips
| Operated by | Vehicle type | Departure time | Departure location | Trip duration | Arrival time | Arrival location | Recommended | Price and booking link |
|---|---|---|---|---|---|---|---|---|
 | Bus | Chicago (Bus Station) | Winona St Uni | No tags | ||||
| Bus | Chicago (Bus Station) | Winona St Uni | No tags | ||||
| Bus | Chicago (Bus Station) | Winona St Uni | No tags | ||||
| Bus | Chicago (Bus Station) | Winona St Uni | No tags |
Compare 2 ways to go from Chicago to Winona
Among the sustainable travel choices, the train stands out as the good way to reach Winona. The journey takes about 5 hours 35 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 Chicago to Winona, MN 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 Chicago to Winona?
The cheapest bus tickets from Chicago to Winona start from $184. 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 Chicago to Winona?
The average bus trip duration from Chicago to Winona is 16h 15m, covering a distance of 252 miles (406 km). The quickest bus can get you there in 16h 15m and is operated by Jefferson Lines.
Which bus companies service the Chicago to Winona 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 Chicago to Winona?
The earliest bus departs from Chicago to Winona at 9:15pm. And the latest bus departs at 9:15pm.
What are the CO₂ emissions for the bus trip from Chicago to Winona?
A bus trip from Chicago to Winona 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 Chicago to Winona, MN was searched and found on Dec 22, 2025 with a price of $197To save money and be sure you have the best seat, it's a good idea to buy your bus tickets from Chicago to Winona, MN, as early as possible.
You can expect to pay from $197 to $197 for a bus ticket from Chicago to Winona, MN based on the last 2 days. You can expect to find the cheapest price for the trip at $197 which is on 2025-12-23.
