- Must visit
Minnesota Marine Art Museum
Regional art museum with American art, changing exhibitions, and a strong local connection. A key cultural stop in Winona.
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The cheapest and fastest buses from Chicago, IL to Winona, MN
Showing times, prices and bookable tickets for Oct 21
Cheapest price on Oct 21
$112
Average ticket price on Oct 21
$115
Fastest journey on Oct 21
7 h 9 m
Average journey duration on Oct 21
7 h 22 m
Buses on Oct 21
2
Distance
406 km
Cheap tickets
The best way to find a cheap bus ticket from Chicago, IL to Winona, MN is to book your journey as far in advance as possible and to avoid traveling at rush hour.
The average ticket from Chicago, IL to Winona, MN will cost around $115 if you buy it on the day, but the cheapest tickets can be found for only $112.
Fast buses
It's difficult to get from Chicago, IL to Winona, MN without transferring at least once.
6:00 AM7h35Chicago, IL1:35 PMWinona, MN$1121One-way1 transfer.png)
6:26 AM7h09Chicago, IL1:35 PMWinona, MN$1181One-way2 transfers
- 6:26 AM7h09Chicago, IL1:35 PMWinona, MN$1181One-way2 transfers
- 6:00 AM7h35Chicago, IL1:35 PMWinona, MN$1121One-way1 transfer
Journey information
Overview: Bus from Chicago, IL to Winona, MN
USAUSA
Take a bus from Chicago, IL to Winona, MN and enjoy the approximately 252 miles (406 km) long journey. Find schedules and pricing options for a convenient and affordable trip.
The earliest bus runs at 06:00, the last at 06:26.
Fares are the lowest economy prices found on Omio. Early booking often means lower prices. Prices change daily and are subject to availability. Discount cards, coach trips, and booking fees are not included.
Price information
Cheapest alternative travel mode
Train from $75
Distance 252 miles (406 km) |
First bus 6:00 AM |
Last bus 6:26 AM |
High Season Jan - Mar |
Low Season Jul - Sep |
Busiest Day Wed |
Least Busy Day Wed |
Best time to book 42 days |
Fares are the lowest economy prices found on Omio. Early booking often means lower prices. Prices change daily and are subject to availability. Discount cards, coach trips, and booking fees are not included.
Price information
Cheapest alternative travel mode
Train from $75
Chicago, IL to Winona, MN Bus Timetables
| Operator | Departure Time | Arrival Time | Duration | Departure days | Cheapest price |
|---|---|---|---|---|---|
Operator Vangalder Bus | Departure Time 06:00AM | Arrival Time 01:35PM | Duration 7h35 | Departure days Mon, Wed, Thu, Fri, Sat, Sun | Cheapest price $112 |
Operator Chicago Transit (CTA) | Departure Time 06:18AM | Arrival Time 01:35PM | Duration 7h17 | Departure days Sun | Cheapest price $118 |
Operator Chicago Transit (CTA) | Departure Time 06:24AM | Arrival Time 01:35PM | Duration 7h11 | Departure days Sat | Cheapest price $118 |
Operator Chicago Transit (CTA) | Departure Time 06:26AM | Arrival Time 01:35PM | Duration 7h09 | Departure days Mon, Wed, Thu, Fri | Cheapest price $118 |
Live departures
Chicago, IL to Winona, MN bus times
The table below shows live departures for Chicago, IL to Winona, MN buses for tomorrow, Wednesday, October 21. You can also manually refresh the results below to see updated bus journeys.
Last updated at
| Provider | Departs | Duration | Arrives | Transfers | Tickets |
|---|---|---|---|---|---|
| 6:00 AM Chicago, IL | 7h35 | 1:35 PM Winona, MN | 1 transfer | |
| 6:26 AM Chicago, IL | 7h09 | 1:35 PM Winona, MN | 2 transfers | |
This is the last bus of the day. | |||||
Find all the dates and times for this journey
Complete guide to Winona, MN
Things to do in Winona, MN
Discover the best of Winona, MN — top attractions, local food, transport tips, budget advice, and currency essentials. Plan your perfect Winona, MN trip today.
- Recommended
Winona County History Center
County history museum in a grand former home, featuring exhibits on Winona life, industry, and people. Good for local context.
Polk Museum
University museum with geology, natural history, and cultural exhibits. A useful stop for families and visitors exploring campus.
- Must visit
Garvin Heights City Park
Blufftop park and viewpoint with sweeping views over Winona, the Mississippi, and surrounding bluffs. A classic first stop in the city.
- Must visit
Sugar Loaf
Prominent bluff trail area with a staircase climb and rewarding views over the river valley. A local favorite for active visitors.
- Recommended
Lake Park
Lakeside city park with walking paths, playgrounds, and water views near downtown. Popular for an easy stroll and relaxing scenery.
Tater Tot Hotdish
A hearty Midwestern hotdish baked with meat, vegetables, and a creamy base, reflecting Minnesota church suppers and family tables.
- Gluten-free
Walleye
Walleye from regional lakes, usually pan-fried or broiled. It is a classic Upper Midwest fish dish strongly tied to Minnesota dining.
Wild Rice Soup
A rich wild rice soup often made with cream, vegetables, and chicken. Wild rice is a signature Minnesota ingredient with deep regional roots.
Island City Brewing Company
Modern pizzeria and brewpub with house beers, wood-fired pizzas, and a lively social atmosphere near downtown.
Lakeview Drive Inn
Casual local favorite serving burgers, sandwiches, and bar food in a laid-back downtown setting popular with residents and visitors.
Bub's Brewing Company
Long-running German restaurant and tavern known for schnitzel, sausages, and old-school supper club atmosphere.
US Dollar ($)
Moderate for a small US city. Hotels and dining are usually cheaper than major US tourist hubs, while transport often requires a car or taxi.
Average meal costs
- Budget
- $10-15 for fast food or a simple meal.
- Mid-range
- $18-30 per person for a restaurant meal.
- Fine dining
- $40+ per person for upscale dining.
- Coffee
- $3-5 for a coffee drink.
Tipping culture
Tip 15-20% at restaurants, about 10% for taxis, and $1-2 at cafes for barista service or takeaway.
FAQs: Bus from Chicago, IL to Winona, MN
Find answers to the most common questions about traveling from Chicago, IL to Winona, MN by bus. From journey times and ticket prices to direct connections, first and last departures, and even whether the route is scenic, our FAQs cover everything you need to plan your trip. Whether you’re looking for the fastest bus, the cheapest option, or tips for making the most of your visit at Winona, MN, this guide helps you travel smarter and with confidence.
The earliest bus from Chicago, IL to Winona, MN leaves at 6:00 AM. Plan your trip with the Journey Planner from Omio.
The latest bus from Chicago, IL to Winona, MN leaves at 6:26 AM.
It's helpful to compare your options as there are 3 ways to travel between Chicago, IL and Winona, MN including taking a train, bus, and flight.
No, the bus from Chicago, IL to Winona, MN has no accessibility options.
No, there are no bathrooms on board the bus from Chicago, IL to Winona, MN.
No, bikes are not allowed on board the bus from Chicago, IL to Winona, MN.
Tickets are often cheaper when booked early. Traveling during off-peak hours or on weekdays can help you save money. Sort results by price to quickly identify the most affordable options. Check for promotions or discounts available on our website and app.
No, there is no food available to purchase on board the bus from Chicago, IL to Winona, MN.
No, luggage for the bus from Chicago, IL to Winona, MN needs to be booked in addition.
No, there are no additional luggage options for the bus from Chicago, IL to Winona, MN.
Unfortunately, pets are not allowed on the bus from Chicago, IL to Winona, MN.
No, there are no USB plugs on board the bus from Chicago, IL to Winona, MN.
No, there is no WiFi on board the bus from Chicago, IL to Winona, MN.
The currency used in the United States is the US Dollar (USD). For travelers, using cards is generally more convenient and widely accepted, especially credit and debit cards, while cash is useful for small purchases or places that do not accept cards.
In Winona, MN, travelers should be aware of typical urban safety concerns such as petty theft and vehicle break-ins, especially in busy or tourist-heavy areas. It is advisable to keep personal belongings secure and avoid leaving valuables visible in parked cars. Additionally, travelers should be cautious of unofficial ticket sellers or offers that seem too good to be true when purchasing transportation or event tickets to avoid scams. Staying informed about local alerts and using reputable vendors can help ensure a safe visit.
Pack lightweight, versatile clothing suitable for the destination's climate, and use secure, lockable luggage to protect belongings. Keep essential items like travel documents, medication, and valuables in a carry-on bag for easy access. Use packing organizers or cubes to maximize space and maintain order. Lastly, include a small first aid kit and personal hygiene items for added comfort during travel.
Most popular bus connections from Chicago, IL
More options for your journey from Chicago, IL to Winona, MN
Here are some other resources that might have the information you need
Most popular buses to and from Winona, MN and Chicago, IL
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