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Chicago, IL, USA to Winona, MN, USA from $12: 6 ways by bus, train, flight or car

Compare Travel Options and Prices

from
Chicago, United States of America
to
Winona, United States of America

How to Get from Chicago to Winona: Cheapest, Fastest and Best Way

1Map provides directions to cities, towns, landmarks, attractions, and addresses worldwide, offering thousands of multi-modal routes to easily get you from point A to point B.

$12 by trainBest price
409 kmDistance
3h 35m Fastest

Compare Train, Bus, Flight, and Driving Options

Get detailed, step-by-step directions below for your trip from Chicago to Winona with 1Map travel planner. Easily compare ticket prices, explore various transport options, and find the best routes for a seamless and cost-effective travel experience.

Company
Amtrak
Train
Average Duration
5h  29m
Estimated price
$12-130
Recommended
route map
Distance: 409 km
Duration: 3h 35m

See more options

Company
various
Drive
Average Duration
5h 
Estimated price
$55-85
Company
Amtrak Thruway Connecting Service / Milwaukee
Bus
Average Duration
8h 
Estimated price
$59-124
Company
Southwest Airlines / Amtrak
Plane
Train
Average Duration
6h  37m
Estimated price
$120-558
Company
American Airlines / various
Plane
Bus
Average Duration
6h  10m
Estimated price
$188-504
Company
American Airlines
Plane
Average Duration
3h  35m
Estimated price
$328-635
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Traveling From Chicago to Winona

Your journey from the vibrant city streets of Chicago to the serene landscapes of Winona offers a striking contrast between urban energy and small-town charm.

Best Neighbourhoods in Winona

Winona offers a blend of charming neighborhoods, each with its own character.

Downtown Winona
• Vibrant dining and shopping options available.
• Historic architecture enhances the ambiance.
East End
• Beautiful views of the Mississippi River.
• Family-friendly parks and recreational areas.
West Winona
• Quaint residential areas with local charm.
• Close to scenic hiking trails and nature spots.

Best Times To Visit Winona's Attractions

Timing your visit to Winona's attractions can greatly enhance your experience.

Garvin Heights Park
Visit early morning or late afternoon for stunning views and fewer crowds.
Lake Winona
Weekdays provide a quieter atmosphere for picnics and walks.
Minnesota Marine Art Museum
Consider visiting on Thursdays, when admission is discounted and less crowded.

Winona Weather: What to Expect Year-Round

Winona experiences a continental climate, with warm summers and cold winters, making summer and early fall the most pleasant times to visit. Be mindful of seasonal changes, as weather can influence outdoor activities and sightseeing options significantly.

Dining Recommendation in Winona

Try the wild rice soup at the Blue Heron Coffee House, which showcases the local flavors and ingredients of the region, offering a rustic yet inviting atmosphere that’s a refreshingly different experience from the bustling culinary scene of Chicago.

Chicago - Winona operators

Explore transport companies operating between Chicago and Winona, with prices starting at . These companies offer competitive pricing, flexible schedules, and comfortable travel experiences.

Train
Contact phone
+1 800-872-7245
Website
https://www.amtrak.com/home.html

Train from Chicago Union Station to Winona

Average Duration
5h 29m
Estimated price
$12-130
Bus
Contact phone
+1 800-872-7245
Website
https://www.amtrak.com/home.html

Bus from Chicago Union Station to Winona State University, MN via Madison

Average Duration
8h
Estimated price
$59-124
Contact phone
+1-858-800-8898
Website
jeffersonlines.com

Bus from Madison, WI-Lake St. to Winona State University, MN

Average Duration
Estimated price
$0-0
Drive

Drive from Chicago to Winona

Average Duration
5h
Estimated price
$55-85
Plane
Website
aa.com

Plane from Chicago O'Hare (ORD) to La Crosse (LSE)

Average Duration
1h 24m
Estimated price
$123-122

Plane from Chicago O'Hare (ORD) to Rochester (RST)

Average Duration
1h 21m
Estimated price
$123-550
Website
southwest.com

Plane from Chicago Midway (MDW) to Minneapolis (MSP)

Average Duration
1h 25m
Estimated price
$124-125
Website
delta.com

Plane from Chicago Midway (MDW) to Minneapolis (MSP)

Average Duration
1h 36m
Estimated price
$126-550

Chicago to Winona: Overview of Bus, Train, Flight, and Car Trips

Traveling between Chicago and Winona offers a variety of convenient options to suit your preferences, schedule, and budget. Whether you prioritize affordability, speed, or comfort, you’re sure to find the perfect way to travel without compromising on quality or convenience.

🚗 Embark on a scenic road trip from the bustling city of Chicago to the charming town of Winona, covering a distance of 307 miles. 🌳 Enjoy approximately 5 hours of picturesque Midwest landscapes and charming small towns along the way. 💰 Prices for a car journey from Chicago to Winona typically range from $55 to $85, providing an affordable and convenient travel option for those seeking a peaceful getaway. 🛣️ Experience the freedom of the open road as you navigate through beautiful countryside and quaint rural communities.
Average price
$55 - $85
🚂 Traveling by train from Chicago to Winona is a convenient and scenic journey. The direct train service operated by Amtrak departs five times a day from Chicago Union Station, taking approximately 5 hours and 29 minutes to reach Winona. 💰 Ticket prices for the Chicago to Winona train journey range from $12 to $130, offering flexibility for travelers with different budgets. Whether you're planning a day trip or a longer stay in Winona, taking the train is a comfortable and cost-effective way to travel between these two cities.
Departure Point
Chicago Union Station
Arrival Point
Winona station
🛫 Flying from Chicago to Winona is a convenient option, with a direct flight from Chicago O'Hare Airport to La Crosse Airport taking just 1 hour and 18 minutes. American Airlines provides flights for this route, ensuring a smooth journey. 🌄 Once you land at La Crosse Airport, the total travel time to reach Winona from Chicago by plane is approximately 3 hours and 35 minutes. This is a relatively quick and efficient way to travel between the two cities. 💸 Flight prices between Winona and Chicago can vary, typically ranging from $328 to $635.
Departure Point
Chicago O'Hare Airport
Arrival Point
La Crosse Airport
🛤️ The journey by bus from Chicago to Winona, including transfers, typically takes around 8 hours. Amtrak operates the service departing from Chicago Union Station. 💰 Bus fares between Winona and Chicago can vary from $59 to $124, offering an affordable and convenient travel option for those looking to explore the route by land.
Departure Point
Chicago Union Station
Arrival Point
Winona State University, MN station

Frequently asked questions

Find out more about the route from Chicago to Winona.

Or choose the category:
The distance between Chicago and Winona is 254 miles, or 307 miles by road. The typical travel times by various modes of transportation are as follows: It takes 5 hours and 29 minutes to reach Winona from Chicago by train, 4 hours and 40 minutes by flying from Chicago O'Hare to La Crosse and then taking a train. If driving, it takes approximately 5 hours to reach Chicago from Winona by car. The longest travel time is by bus, which takes around 8 hours to reach Winona from Chicago.
The most cost-effective option for traveling from Chicago to Winona is by train, which can cost anywhere from $12 to $130 and takes approximately 5 hours and 29 minutes. However, if time is a priority and budget is not a constraint, the quickest option is to fly from Chicago O'Hare to La Crosse and then take a train to Winona, which takes around 4 hours and 40 minutes and can cost between $270 and $750. Overall, the train option offers a good balance between cost and travel time.
When traveling from Chicago to Winona the prices for a train ticket vary from $12 to $130. The cost of a bus ticket between Winona and Chicago ranges from $59 to $124. These prices may be subject to change and can vary depending on factors such as time of booking, availability, and the class of service chosen. It is recommended to check with the respective transportation providers for the most accurate and up-to-date pricing information.
To get from Chicago to Winona without using public transportation, you can drive the distance of approximately 307 miles. The drive typically takes around 5 hours, depending on traffic conditions. The cost of a car rental for this journey can range from $55 to $85, depending on the company and the type of vehicle.
The most convenient way to travel from Chicago to Winona without a car is by train. The journey takes approximately 5 hours and 29 minutes and ticket prices range from $12 to $130. The train provides a comfortable and scenic route, allowing you to relax and enjoy the journey.
Yes, there is a direct train link between Chicago and Winona. The Amtrak train departs from Chicago Union Station and arrives at Winona Station, with services available five times a day. The journey takes approximately 5 hours and 29 minutes. However, there is no direct bus route between the two cities. Passengers would need to take a bus from Chicago Union Station to Madison, WI, and then transfer to another bus to reach Winona State University with the total journey time being around 8 hours.
The flight from Chicago to Winona typically takes 1 hour and 14 minutes on a direct flight from Chicago O'Hare Airport to La Crosse Airport. The cost of the flight can vary depending on the airline and ticket availability, but it is typically around $200 to $300. It is important to note that these times and prices are subject to change and may vary based on factors such as airline schedules and seasonal fluctuations.
There are several hotels available in Winona for travelers to choose from. Prices for accommodations start at $41 per night. Some popular options include the AmericInn by Wyndham Winona, the Holiday Inn Express & Suites Winona, and the Plaza Hotel & Suites. These hotels offer a range of amenities and convenient locations for visitors to enjoy their stay in Winona.

Trips from Chicago