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Journey Information
There are 3 intercity buses per day from Winona to Chicago. Traveling by bus from Winona to Chicago usually takes around 8 hours and 5 minutes, but the fastest FlixBus US bus can make the trip in 7 hours and 15 minutes.
| Distance | 253 mi (408 km) |
| Shortest duration | 7h 15m |
| Cheapest price | $39.89 |
| Most frequent service | FlixBus US |
| Bus lines | 1 |
What bus companies travel from Winona to Chicago?
There is one intercity bus company available to search and book on Wanderu that operates from Winona to Chicago. FlixBus US connects the two cities by bus, it offers multiple scheduled buses per day for you to choose from.
| Bus | Daily Trips | Avg. Time | Avg. Price |
|---|---|---|---|
| FlixBus US | 3 | 8h 6m | $58.53 |
FlixBus US is the American branch of German bus company FlixBus, known for providing sustainable, affordable, and modern bus travel. The company offers cheap bus tickets to popular urban destinations throughout the United States. FlixBus US buses include many amenities, including comfortable seats, free WiFi, power outlets at every seat, and an online portal for free entertainment. On average, FlixBus US operates 3 trips per day from Winona to Chicago, and the average ticket for this route costs only .
Frequently Asked Questions
The bus takes an average of 8 hours and 5 minutes to cover the 253 miles from Winona to Chicago. However, the fastest bus only takes 7 hours and 15 minutes. It’s definitely on the longer side, so plan to get comfortable for a long road trip. Keep in mind that your actual bus may arrive earlier or later than scheduled, depending on whether there is more or less traffic than usual.
Tuesday is usually the day of the week when buses are busiest. If you are planning to travel on a Tuesday, you should make sure to book tickets well in advance as they may sell out.
On the other hand, Sunday is typically the least busy day for bus travel on this route. If you are looking for less crowded buses to Chicago, book your ticket for the last day of the week.
The first bus leaves at 1:00pm and the last bus leaves at 1:00pm. To see the times for all buses from Winona to Chicago, enter your specific travel dates in the search bar.
There are 3 scheduled buses that travel from Winona to Chicago every day, so you have a decent number of options to choose from. Unfortunately, none of them are direct connections, so no matter which bus you take, you will have to transfer buses at least once during your journey.
Need more travel options? Consider taking the train from Winona to Chicago; ticket prices start at $50.00.
City Information
Chicago
Known for its innovative architecture, cultural contributions to jazz and house music, and of course that irresistible deep-dish pizza, the many sights and experiences in Chicago make it one of the best urban vacation destinations for millennials and a top destination in Illinois.
You can't beat the views of the city and Lake Michigan from the SkyDeck in the Willis Tower; at over 1,300 feet, this is the highest observation deck in the U.S. Snap that classic selfie with the Bean in Millennium Park, then wander the many museums in nearby Grant Park. Navy Pier is a popular tourist hotspot for its parks, restaurants, and attractions right on Lake Michigan, and baseball fans will find paradise in Wrigleyville, home to the Chicago Cubs' Wrigley Field and sports bars galore.
Chicago's enormous parks offer plentiful opportunities for outdoor activities in gorgeous urban settings. Many companies offer kayak rentals or boat tours on the Chicago River, with special tours running on Saint Patrick's Day, when the entire river is dyed green. When you’re ready to buy some souvenirs from your epic trip, hit the big brand stores on the Magnificent Mile, or shop local in neighborhoods like Andersonville and Wicker Park. And don't miss the chance to laugh until you cry at The Second City comedy theater, famous for launching the careers of comedians like Tina Fey and Stephen Colbert.
Chicago is one of the biggest transportation hubs in the Midwest, and provides easy access to nearby destinations ideal for day trips, as well as international travel from two airports. Thanks to plenty of bus and train stations throughout the city, getting to the Windy City is a breeze.
Station Information
Where does the bus leave from in Winona?
Main departure station: Winona State University
Most buses depart from the main station in Winona.
All bus stations in Winona:
Winona State University
Where does the bus arrive in Chicago?
Main arrival station: Dan Ryan Bus Station
Buses arrive in Chicago at 3 stations, depending on which bus line you are traveling with.
All bus stations in Chicago:
Dan Ryan Bus Station
5800 N Cumberland Ave
Bus Station - 630 W Harrison St
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Need a return trip from Chicago to Winona?
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