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: Last Wednesday at 10:37 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 $266
Frequently asked questions about travelling from Winona, MN to Chicago by bus
How far is Winona from Chicago?
Winona and Chicago are 408 km (253 miles) apart.
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 21, 2025 with a price of $285To 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 $285 to $285 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 $285 which is on 2025-11-24.
