Next bus departures
| 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 | CheapestFastest |
Last refresh of the prices: Yesterday at 1:09 PM CST.
Compare 2 ways to travel from Chicago to Winona
Among the sustainable travel choices, the train stands out as a good way to reach Winona. The journey takes about 5 hours 35 minutes and with fares starting at just R 662, it presents an excellent value for a comfortable ride.
Compare bus companies
Based on 759 reviews, the company was rated 3.9 stars on Busbud. Travellers were especially satisfied with the temperature and the seats but often complained with the Wi-Fi. Jefferson Lines ticket prices on this trip start at R 3 160
Frequently asked questions about travelling from Chicago to Winona, MN by bus
Please note that timetables, routes, or operator details shown here may be updated or differ 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 at R 3 160. The average price for this route is around R 3 160. Busbud recommends booking your tickets in advance for the best chance of getting the lowest possible price.
How long is the bus journey from Chicago to Winona?
The average bus journey time from Chicago to Winona is 16h 15m, covering a distance of 406 km. The fastest bus gets you there in 16h 15m and is operated by Jefferson Lines.
Which bus companies service the Chicago to Winona route?
Several major bus companies operate on this route with 1 buses 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 21:15. And the latest bus departs at 21:15.
What are the CO₂ emissions for the bus trip from Chicago to Winona?
A bus trip from Chicago to Winona produces an estimated 10 kg of CO₂, making it a highly eco-friendly travel option and Busbud’s recommended way to travel.
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 14 Dec 2025 with a price of R 3 080To 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 R 3 080 to R 3 389 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 R 3 080, which is on 2025-12-16.
