What is the cheapest way to get from Chicago to Winona?

The cheapest way to get from Chicago to Winona is to drive which costs $55 - $85 and takes 4h 56m.

What is the fastest way to get from Chicago to Winona?

The fastest way to get from Chicago to Winona is to fly and taxi which takes 3h 32m and costs $100 - $350.

Is there a direct bus between Chicago and Winona?

No, there is no direct bus from Chicago to Winona. However, there are services departing from W Jackson Blvd, after S Clinton St and arriving at Winona State Univ. via Madison. The journey, including transfers, takes approximately 8h 15m.

Is there a direct train between Chicago and Winona?

Yes, there is a direct train departing from Chicago Union Station station and arriving at Winona. Services depart three times a day, and operate every day. The journey takes approximately 5h 29m.

How far is it from Chicago to Winona?

The distance between Chicago and Winona is 308 miles. The road distance is 306.8 miles.

How do I travel from Chicago to Winona without a car?

The best way to get from Chicago to Winona without a car is to train which takes 5h 29m and costs $50 - $160.

How long does it take to get from Chicago to Winona?

The train from Chicago Union Station to Winona takes 5h 29m including transfers and departs three times a day.

Where do I catch the Chicago to Winona bus from?

Chicago to Winona bus services, operated by Vangalder Bus, depart from W Jackson Blvd, after S Clinton St station.

Where do I catch the Chicago to Winona train from?

Chicago to Winona train services, operated by Amtrak, depart from Chicago Union Station.

Train or bus from Chicago to Winona?

The best way to get from Chicago to Winona is to train which takes 5h 29m and costs $50 - $160. Alternatively, you can bus, which costs $35 - $130 and takes 8h 15m.

Where does the Chicago to Winona bus arrive?

Chicago to Winona bus services, operated by Vangalder Bus, arrive at 250 N. Lake St - Madison UW Campus station.

Where does the Chicago to Winona train arrive?

Chicago to Winona train services, operated by Amtrak, arrive at Winona station.

Can I drive from Chicago to Winona?

Yes, the driving distance between Chicago to Winona is 307 miles. It takes approximately 4h 56m to drive from Chicago to Winona.

How do I get a train ticket from Chicago to Winona?

Book your Chicago to Winona train tickets online with Omio.

Where can I stay near Winona?

There are 13+ hotels available in Winona.

Chicago to Winona - 4 ways to travel via train, bus, car, plane, and taxi

There are 4 ways to get from Chicago to Winona by train (Amtrak), bus, car, plane, or taxi

Select an option below to see step-by-step directions and to compare ticket prices and travel times in Rome2Rio's travel planner.

Train (Amtrak)
best
1. Take the train from Chicago Union Station to WinonaEmpire Builder / ...
5h 29m
$50–160
Bus
cheapest
1. Take the bus from W Jackson Blvd, after S Clinton St to 250 N. Lake St - Madison UW CampusVan Galder
2. Take the bus from Madison to Winona State Univ.Jefferson 966
8h 15m
$37–126
Drive 305 mi
1. Drive from Chicago to Winona305 mi
4h 56m
$56–81
Fly, taxi
1. Fly from Chicago O'Hare International Airport (ORD) to La Crosse (LSE)ORD - LSE
2. Take the taxi from La-Crosse-Airport-LSE to Winona
3h 32m
$102–345

Chicago to Winona by train (Amtrak)

21Weekly Trains

5h 29mAverage Duration

$50Cheapest Price

See schedules

Questions & Answers

Map of how to get from Chicago to Winona.

Launch map view

Distance: 306.4 mi
Duration: 5h 29m

What companies run services between Chicago, IL, USA and Winona, MN, USA?

Amtrak operates a train from Chicago Union Station to Winona 3 times a day. Tickets cost $50–160 and the journey takes 5h 29m. Alternatively, you can take a bus from W Jackson Blvd, after S Clinton St to Winona State Univ. via Madison in around 8h 15m.

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