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 10:41 PM CST.
Compare 2 ways to go 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 $56, 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 WiFi. Jefferson Lines ticket prices on this trip start at $265
Frequently asked questions about travelling 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 $265. The average price for this route is around $265. 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 travel time from Winona to Chicago is 16h, covering a distance of 406 km. The quickest bus can get 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 are the earliest and latest departure times for the bus from Winona to Chicago?
The earliest bus departs from Winona to Chicago at 1:45pm. And the latest bus departs at 1:45pm.
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 a mode of travel recommended 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 Nov 26, 2025 with a price of $284To 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 $284 to $284 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 $284 which is on 2025-11-30.
