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4.9
4.6The cheapest and fastest buses from Chicago, IL to Winona, MN
Cheapest price on Sep 06
$115
Average ticket price on Sep 06
$118
Fastest journey on Sep 06
7 h 17 m
Average journey duration on Sep 06
7 h 26 m
Buses on Sep 06
2
Distance
406 km
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 $118 if you buy it on the day, but the cheapest tickets can be found for only $115.
It's difficult to get from Chicago, IL to Winona, MN without transferring at least once.
6:00 AM7h35Chicago, IL1:35 PMWinona, MN$1151One-way1 transfer.png)
6:18 AM7h17Chicago, IL1:35 PMWinona, MN$1211One-way2 transfers
- 6:18 AM7h17Chicago, IL1:35 PMWinona, MN$1211One-way2 transfers
- 6:00 AM7h35Chicago, IL1:35 PMWinona, MN$1151One-way1 transfer
Travel Information
Compare train, bus, and flight for Chicago, IL to Winona, MN
Omio recommends booking the train as it is the most popular option from Chicago, IL to Winona, MN among Omio's users. If you are prioritising price, take the train, with an average ticket price of $92 For those with little time, consider booking a flight, which has an average total journey time of 3h 25m. Average ticket prices depend on the travel mode: a train costs an average of $92, while a flight costs an average of $385.
Distance: 252 miles (406 km)
Compare bus with
| Bus | Most popular Train | Flight | Driving |
|---|---|---|---|
$118 Average price | $92 Average price Cheapest | $385 Average price | $68 Average price (fuel + tolls) |
7h 53m Average total duration 7h 23m Onboard + 30m Additional time* | 6h 3m Average total duration 5h 33m Onboard + 30m Additional time* | 3h 25m Average total duration Fastest 1h 25m Onboard + 2h 0m Additional time* | 5h 34m Average total duration (door-to-door) |
Direct Options | Direct Options | Direct Options | Direct Options |
This is compared to other travel options from Chicago, IL to Winona, MN:
A train is $27 (€21) less than a bus for this route with tickets for a bus from Chicago, IL to Winona, MN costing on average $118 (€96).
A train is $294 (€237) less than a flight for this route with tickets for a flight from Chicago, IL to Winona, MN costing on average $385 (€311).
Other travel options to Winona, MN take longer:
Train takes on average 5h 33m.
Bus takes on average 7h 23m.
Tickets start at around $118 (€96) compared to roughly $68 (€55) in fuel and tolls — a saving of about $-50.21 (€-40.58). The journey takes 7h 23m versus 5h 34m by car, so you'll arrive a bit later, but you can use the time productively rather than spending it behind the wheel. No parking to sort, no fuel stops, and most coaches have Wi-Fi and power outlets.
Driving is worth considering if you're on a tight schedule, travelling as a group (where fuel costs split several ways), or want the flexibility to stop along the way.
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 $115 |
Operator Chicago Transit (CTA) | Departure Time 06:18AM | Arrival Time 01:35PM | Duration 7h17 | Departure days Sun | Cheapest price $121 |
Operator Chicago Transit (CTA) | Departure Time 06:24AM | Arrival Time 01:35PM | Duration 7h11 | Departure days Sat | Cheapest price $121 |
Operator Chicago Transit (CTA) | Departure Time 06:26AM | Arrival Time 01:35PM | Duration 7h09 | Departure days Mon, Wed, Thu, Fri | Cheapest price $121 |
Live departures
Chicago, IL to Winona, MN bus times
The table below shows live departures for Chicago, IL to Winona, MN buses for today, Saturday, September 5. You can also manually refresh the results below to see updated bus journeys.
| Provider | Departs | Duration | Arrives | Transfers | Tickets |
|---|---|---|---|---|---|
| 6:00 AM Chicago, IL | 7h35 | 1:35 PM Winona, MN | 1 transfer | |
| 6:24 AM Chicago, IL | 7h11 | 1:35 PM Winona, MN | 2 transfers | |
This is the last bus of the day. | |||||
Find all the dates and times for this journey
Compare prices and tickets Chicago, IL to Winona, MN by train, bus, or flight
Compare train, bus, and flight prices over the next three weeks. See the best deals at a glance, find the lowest fares, and choose the option that fits your budget.
Sep 06
Sep 07
Sep 08
Sep 09
Sep 10
Sep 11
Sep 12
Journey information
Overview: Bus from Chicago, IL to Winona, MN
USAUSA
Buses from Chicago, IL to Winona, MN run on average 2 times per day, taking around 7h 23m. Cheap bus tickets for this journey start at $115 (€93) but you can travel from only $41 (€33) by train.
The earliest bus runs at 06:00, the last at 06:26. The fastest bus covers the 252 miles (406 km) distance in 7h 9m.
Distance 252 miles (406 km) |
Average bus duration 7h 23m |
Cheapest ticket price $115 (€93) |
Buses per day 2 |
Fastest bus 7h 9m |
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 |
Bus providers: Vangalder Bus, Chicago Transit (CTA) from Chicago, IL to Winona, MNYou can travel by bus between Chicago, IL to Winona, MN with Vangalder Bus, Chicago Transit (CTA) for as low as $41 (€33). When you search for schedules and tickets, Omio will show you the best journey
Vangalder Bus
Chicago Transit (CTA)
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.
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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