- Chicago to Winona buses
Next departures
| Operated by | Vehicle type | Departure time | Departure location | Trip duration | Arrival time | Arrival location | Recommended | Price and booking link | 
|---|---|---|---|---|---|---|---|---|
|  | Chicago (Bus Station) | Winona St Uni | CheapestFastest | 
Last refresh of the prices: Last Wednesday at 5:40 AM CDT.
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Compare 2 ways to go 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 US$39, it presents an excellent value for a comfortable ride.
Bus Chicago to Winona, MN: Trip Overview
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 US$184
Chicago to Winona Bus
With Busbud, comparing and booking tickets for a bus from Chicago to Winona is a breeze. Browse through an extensive selection of bus fares and bus schedules to find the best deals.
We make it our job to connect you with the most dependable bus companies that cover bus service from Chicago to Winona.
Whether it is cheap bus tickets or more luxurious buses going to Winona from Chicago, we help you find what you're looking for based on how much of a budget you have.
Frequently asked questions on the trip Chicago - Winona, MN
- What is the distance between Chicago and Winona?- The distance between Chicago and Winona is around 408 km (253 miles). 
Find cheapest prices for buses
Price is for a one-way ticket for one passenger and based on past searches.
To 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 US$179 to US$179 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 US$179 which is on 2025-11-02.
About Bus Travel
Bus Travel Tips
Meet and talk to locals at the bus stations while travelling from Chicago to Winona.There is no better way to get inside travel information while exploring a new city than to go straight to its people.
From miles long of beauteous natural landscapes to impressive man-crafted sights, you’re bound to be in for a visual treat on your bus trip from Chicago to Winona.
Buses are energy-efficient. Carrying a passenger over 100 kms by coach only takes 0.6-0.9 liters of gas. Compare that to the 2.6 liters required by high-speed train, 6.6 liters by airplane and 7.6 liters by gas-powered car, and it's clear that the bus is a more environmentally-conscious option for your bus transportation from Chicago to Winona.
Tune out to the fine sounds of your best music playlist on your bus trip from Chicago to Winona while indulging in miles on end of beautiful scenic views.
Did you know?
Did you know some bus companies in Germany offer to their passenger low-costs snacks and regional beer based on their destination? Prosit!
The Superbus, created by a Dutch engineer is the world's fastest bus with 250 km/h. Too bad it's only a prototype for now.
9.2% of ground transportation in Europe is done by bus versus 7.4% by train.
Top travelled bus routes
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