Bus Tickets from Winona, MN to Chicago

Next departures

Next departures for Winona to Chicago on September 30
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: Last Thursday at 8:33 AM CDT.

Accepted payments

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Compare 2 ways to go from Winona to Chicago.

Bus
Average Price$184 - $184Average Duration16h 20m
10kg CO₂e5 out of 5 stars
Most eco-friendly
Train
Average Price$39 - $387Average Duration5h 50m
37kg CO₂e1 out of 5 stars
CheapestFastest
busbud logoBusbud recommends taking the train from Winona to Chicago

Among the sustainable travel choices, the train stands out as the good way to reach Chicago. The journey takes about 5 hours 50 minutes and with fares starting at just $39, it presents an excellent value for a comfortable ride.

3train per day
5h 50mAverage Duration
$39Cheapest ticket
37kgCO₂ emissions

Bus Winona, MN to Chicago: Trip Overview

Average ticket price$184
Average bus trip duration16h 20m
Number of daily buses1
Earliest bus departure1:45pm
Distance252 miles (405 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 traveling 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 for your trip Winona, MN - Chicago

Find cheapest prices for buses

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

Best price found
09/25
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09/26
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Today
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09/28
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09/29
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09/30
$179
10/01
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10/02
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busbud logoThe cheapest trip from Winona, MN to Chicago was searched and found on Sep 30, 2025 with a price of $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 $179 to $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 $179 which is on 2025-09-30.

About Bus Travel

Bus Travel Tips

Meet and talk to locals at the bus stations while traveling 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.

You can also go to Chicago by train

Train from Winona, MN to Chicago

Why choose Busbud?

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