Find coaches from Chicago to Winona, MN

Previously seen journeys

Next departures from Chicago to Winona on 3 November
Operated byVehicle typeDeparture timeDeparture locationTrip durationArrival timeArrival locationRecommendedPrice and booking link
Jefferson Lines
    		Chicago (Bus Station)
    		Winona St UniNo tags

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    Compare 2 ways to travel from Chicago to Winona

    We recommend taking the train

    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.

    3train per day
    5h 35mAverage duration
    405 kmDistance
    37kgCO₂ emissions
    Bus
    		Average priceUS$184 - US$184Average duration16h
    10kg CO₂e
    Train
    		Average priceUS$39 - US$627Average duration5h 35m
    37kg CO₂e

    Bus Chicago to Winona, MN: Trip Overview

    Average ticket priceUS$184
    Average bus trip duration16h
    Number of daily buses1
    Earliest bus departure21:30
    Distance405 km

    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

    1. How much does a bus ticket from Chicago to Winona cost?

      The bus ticket price from Chicago to Winona starts at US$184. The best way to find cheap bus tickets from Chicago to Winona is to book your tickets as early as possible. Prices tend to rise as your travel date approaches, so book in advance to secure the best prices!

    2. How long is the bus ride from Chicago to Winona?

      The average travel time between Chicago and Winona is around 16h, although the fastest bus will take about 16h. This is the time it takes to travel the 408 km that separates the two cities.

    3. How many daily bus connections are there between Chicago and Winona?

      The number of buses from Chicago to Winona can differ depending on the day of the week. On average, there are 1 on this route. Some buses run direct routes, while others have layovers. Simplify your bus trip from Chicago to Winona by comparing and selecting the bus that fits your travel style and budget on Busbud.

    4. Which bus companies travel from Chicago to Winona?

      When taking the bus from Chicago to Winona, you can travel comfortably and safely with Jefferson Lines.

    Find cheapest prices for buses

    Price is for a one-way ticket for one passenger and based on past searches.

    Best price found
    01/11
    No data
    02/11
    US$179
    Today
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    04/11
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    busbud logoThe cheapest trip from Chicago to Winona, MN was searched and found on 02 Nov 2025 with a price of US$179

    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.

    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.

    Will you be returning to Chicago by bus?

    Bus from Winona, MN to Chicago

    You can also go to Winona, MN by train

    Train from Chicago to Winona, MN

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