Find coaches from Winona, MN to Chicago

Next departures

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

Last refresh of the prices: Today at 5:58 AM CDT.

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Compare 2 ways to travel from Winona to Chicago

busbud logoWe recommend taking the train

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 US$39, it presents an excellent value for a comfortable ride.

3train per day
5h 44mAverage duration
405 kmDistance
37kgCO₂ emissions
Bus
Average priceUS$184 - US$184Average duration16h 20m
10kg CO₂e
Train
Average priceUS$39 - US$281Average duration5h 44m
37kg CO₂e

Bus Winona, MN to Chicago: Trip Overview

Average ticket priceUS$184
Average bus trip duration16h 20m
Number of daily buses1
Earliest bus departure13:45
Distance405 km

Winona to Chicago Bus

With Busbud, comparing and booking tickets for a bus from Winona to Chicago 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 Winona to Chicago.

From cheap bus tickets to more luxurious buses travelling from Winona to Chicago, we offer a wide range of bus services to best suit your needs depending on how much your budget is.

Frequently asked questions on the trip Winona, MN - Chicago

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

    The bus ticket price from Winona to Chicago starts at US$184. The best way to find cheap bus tickets from Winona to Chicago 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 Winona to Chicago?

    The average travel time between Winona and Chicago is around 16h 20m, although the fastest bus will take about 16h 20m. 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 Winona and Chicago?

    The number of buses from Winona to Chicago 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 Winona to Chicago by comparing and selecting the bus that fits your travel style and budget on Busbud.

  4. Which bus companies travel from Winona to Chicago?

    When taking the bus from Winona to Chicago, 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
28/10
No data
29/10
US$179
Today
US$179
31/10
No data
01/11
No data
02/11
US$179
03/11
No data
04/11
No data
busbud logoThe cheapest trip from Winona, MN to Chicago was searched and found on 29 Oct 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 Winona, MN to Chicago as early as possible.

You can expect to pay from US$179 to US$179 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 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 Winona to Chicago.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 Winona to Chicago.

Taking the bus creates the smallest carbon footprint compared to other modes of transport. Not to mention that buses will allow you to discover scenic gems from Winona to Chicago that are otherwise impossible to come by with a plane.

Tune out to the fine sounds of your best music playlist on your bus trip from Winona to Chicago while indulging in miles on end of beautiful scenic views.

Did you know?

One of the longest bus route in the world goes all the way from Ontario to Alberta in Canada (with the same bus). This trip is 3,435 km or 2,135 miles long and the price is a bit under $100.

Did you know some bus companies in Germany offer to their passenger low-costs snacks and regional beer based on their destination? Prosit!

It takes 27 hours to go by bus from Lima to Cusco, one of the craziest bus trips on the world. This route is used daily by locals and backpackers.

Will you be returning to Winona, MN by bus?

Bus from Chicago to Winona, MN

You can also go to Chicago by train

Train from Winona, MN to Chicago

Why choose Busbud?

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