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: Today at 00:24 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 £31, 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 £144
Frequently asked questions about travelling by bus from Winona, MN to Chicago
What's the distance between Winona and Chicago by coach?
The journey from Winona to Chicago by coach covers an approximate distance of 253 miles (408 km).
How can I travel from Winona to Chicago avoiding air travel?
To travel from Winona to Chicago without flying, you can take the coaches. The coach ensures a pleasant travel experience, granting you the opportunity to appreciate the scenery as you make your way to your final stop. You also have the option of utilising carpooling services.
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 21 Nov 2025 with a price of £155To 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 £155 to £155 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 £155, which is on 2025-11-24.
