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 6:12 PM CST.
Compare 2 ways to travel from Winona to Chicago
Among the sustainable travel choices, the train stands out as a good way to reach Chicago. The journey takes about 5 hours 44 minutes and with fares starting at just R 666, 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 3 177
Frequently asked questions about travelling from Winona, MN to Chicago 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 Winona to Chicago?
The cheapest bus tickets from Winona to Chicago start at R 3 177. The average price for this route is around R 3 177. Busbud recommends booking your tickets in advance for the best chance of getting the lowest possible price.
How long is the bus journey from Winona to Chicago?
The average bus journey time from Winona to Chicago is 16h, covering a distance of 406 km. The fastest bus gets you there in 16h and is operated by Jefferson Lines.
Which bus companies service the Winona to Chicago 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 Winona to Chicago?
The earliest bus departs from Winona to Chicago at 13:45. And the latest bus departs at 13:45.
What are the CO₂ emissions for the bus trip from Winona to Chicago?
A bus trip from Winona to Chicago 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 Winona, MN to Chicago was searched and found on 15 Dec 2025 with a price of R 3 096To 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 R 3 096 to R 3 407 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 R 3 407, which is on 2025-12-18.
