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Winona, MN, USA to Chicago, IL, USA from $12: 4 ways by bus, train, flight or car

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

How to Get from Winona to Chicago: 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
2h 39m Fastest

Compare Train, Bus, Flight, and Driving Options

Get detailed, step-by-step directions below for your trip from Winona to Chicago 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
American Airlines
Plane
Average Duration
2h  39m
Estimated price
$328-633
Recommended
Company
Amtrak
Train
Average Duration
5h  44m
Estimated price
$12-130
Cheapest
route map
Distance: 409 km
Duration: 2h 39m

See more options

Company
Various
Drive
Average Duration
5h 
Estimated price
$55-85
Company
Jefferson Lines/Amtrak Thruway Connecting Service
Bus
Average Duration
7h  48m
Estimated price
$58-121
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Traveling From Winona to Chicago

Traveling from Winona to Chicago offers a striking contrast between the serene beauty of the Mississippi River Valley and the vibrant urban energy of a bustling metropolis.

Best Neighbourhoods in Chicago

Chicago’s neighborhoods each offer distinct experiences and vibrant atmospheres.

Wicker Park
• Trendy boutiques and hip cafes abound.
• A lively arts scene with local music venues.
Lincoln Park
• Home to beautiful parks and the Lincoln Park Zoo.
• Diverse dining options from casual to fine dining.
The Loop
• Chicago’s bustling business district with iconic architecture.
• Easy access to the Art Institute and theaters.

Best Times To Visit Chicago's Attractions

Timing your visit to Chicago's attractions can enhance your experience significantly.

Millennium Park
Early mornings on weekdays offer a quieter atmosphere and fewer crowds.
Field Museum
Visit mid-afternoon for shorter lines and a more relaxed exploration.
Navy Pier
Late afternoons during weekdays are less crowded, perfect for enjoying sunset views.

Chicago Weather: What to Expect Year-Round

Chicago experiences a diverse climate, with cold winters and hot summers that can greatly influence your travel plans; spring and fall are ideal times to explore the city comfortably. Being prepared for weather variations can enhance your enjoyment of outdoor attractions and events.

Dining Recommendation in Chicago

Try the deep-dish pizza at Giordano's, a quintessential Chicago dish that showcases layers of cheese and a rich tomato sauce, a stark contrast to the lighter fare often found in Winona. The bustling atmosphere and vibrant urban energy of the restaurant scene add an exciting dimension to your dining experience in the city.

Winona - Chicago operators

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

Plane
Website
aa.com

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

Average Duration
1h 19m
Estimated price
$328-650
Train
Contact phone
+1 800-872-7245
Website
amtrak.com

Train from Winona to Chicago Union Station

Average Duration
5h 44m
Estimated price
$12-130
Bus
Contact phone
+1-858-800-8898
Website
jeffersonlines.com

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

Average Duration
Estimated price
$0-0

Bus from Madison to Chicago Union Station

Average Duration
4h
Estimated price
$0-0
Contact phone
+1 608-752-5407
Website
coachusa.com

Bus from Madison, WI-Lake St. to Chicago Union Station

Average Duration
4h
Estimated price
$6-30

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

Traveling between Winona and Chicago 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.

Useful tips for train travellers
On your train trip from Winona to Chicago, you can choose between Amtrak and some regional train services. Amtrak, which operates the Empire Builder and Hiawatha routes, offers Amtrak Café onboard where you can purchase a variety of snacks, light meals, and beverages. Be sure to check out their menu on Amtrak's official site before your trip.
Both Amtrak and regional train services provide a range of seating options. On Amtrak, you'll find Coach Class seats that are spacious and comfortable, as well as Business Class seats that offer extra legroom and complimentary beverages. However, First Class is not available on this route. If you're looking for a quieter atmosphere, opt for Business Class.
When you arrive at Chicago Union Station, you can easily navigate to your next destination. The station offers luggage storage services at the station for a small fee, so you can explore without dragging your bags around. Additionally, make use of the clean restrooms available, and if you need a quick freshen-up, take advantage of the nearby shower facilities available for a fee at fitness centers within walking distance.

Frequently asked questions

Find out more about the route from Winona to Chicago.

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The distance between Winona and Chicago is approximately 254 miles, but the road distance is slightly longer at 306.7 miles. Traveling by train from Winona to Chicago usually takes about 5 hours and 44 minutes. If you opt for a combination of bus and flight, it takes around 3 hours and 55 minutes to reach Chicago, with the first leg of the trip being a bus to La Crosse and then a flight to Chicago O'Hare. Driving from Chicago to Winona typically takes about 5 hours, while taking a bus back to Chicago from Winona takes approximately 7 hours and 48 minutes.
The most cost-effective way to travel from Winona to Chicago is by train, which can cost anywhere from $12 to $130. This option takes approximately 5 hours and 44 minutes. However, if time is of the essence, the quickest way to reach Chicago is by taking a bus to La Crosse and then flying to Chicago O'Hare. This option can cost between $270 and $700 and takes around 3 hours and 55 minutes.
The prices for train tickets between Winona and Chicago can range from $12 to $130, depending on the class and type of ticket. Similarly, the prices for bus tickets between Chicago and Winona can vary between $58 and $121, depending on the bus company and the time of travel. It is always recommended to check the prices in advance and compare different options to find the most suitable and budget-friendly option for your journey.
To get from Winona to Chicago without using public transportation, you can drive the distance of 307 miles. The driving time is approximately 5 hours, depending on traffic conditions. Prices for renting a car to make this journey range from $55 to $85.
The best option to travel from Winona to Chicago without a car is by train. It takes approximately 5 hours and 44 minutes, with ticket prices ranging from $12 to $130. The train journey offers a convenient and comfortable way to reach your destination.
Yes, there is a direct link between Winona and Chicago by train. The journey takes approximately 5h 44m and operates five times a day, every day. However, there is no direct bus route between Winona and Chicago, but there are bus services available with transfers that take approximately 7h 48m. It is recommended to check the schedules and availability with the respective train or bus operators before planning your trip.
The flight from La Crosse Airport to Chicago O'Hare Airport typically takes around 1 hour and 21 minutes. However, it is important to note that this is the quickest flight option. The cost of the flight can vary depending on the airline, time of booking, and other factors, so it is best to check with different airlines for specific prices.
There are numerous hotels available in Chicago, with over 1116 options to choose from. Prices for accommodation start at $58 per night, providing a range of choices to fit different budgets. Visitors to Chicago can find a variety of hotel options throughout the city, offering convenient access to attractions, shopping, dining, and entertainment. It is advisable to book in advance to secure the best rates and availability.

Trips to Chicago