Find coaches from Chicago to Winona, MN

Next departures

Next departures from Chicago to Winona on 2 November
Operated byVehicle typeDeparture timeDeparture locationTrip durationArrival timeArrival locationRecommendedPrice and booking link
Jefferson Lines
Chicago (Bus Station)
Winona St UniCheapestFastest

Last refresh of the prices: Yesterday at 5:40 AM CDT.

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Compare 2 ways to travel from Chicago to Winona

busbud logoWe 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
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02/11
US$179
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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.

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.

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

Why choose Busbud?

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