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

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

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

The fastest way to get from Winona to Chicago is to taxi and fly which takes 2h 40m and costs $100 - $320.

Is there a direct bus between Winona and Chicago?

No, there is no direct bus from Winona to Chicago. However, there are services departing from Winona State Univ. and arriving at W Jackson Blvd, after S Clinton St via 250 N. Lake St - Madison UW Campus. The journey, including transfers, takes approximately 7h 53m.

Is there a direct train between Winona and Chicago?

Yes, there is a direct train departing from Winona and arriving at Chicago Union Station station. Services depart three times a day, and operate every day. The journey takes approximately 5h 44m.

How far is it from Winona to Chicago?

The distance between Winona and Chicago is 262 miles. The road distance is 306.6 miles.

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

The best way to get from Winona to Chicago without a car is to train which takes 5h 44m and costs $50 - $160.

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

It takes approximately 2h 40m to get from Winona to Chicago, including transfers.

Where do I catch the Winona to Chicago bus from?

Winona to Chicago bus services, operated by Jefferson Lines, depart from Winona State Univ. station.

Where do I catch the Winona to Chicago train from?

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

Train or bus from Winona to Chicago?

The best way to get from Winona to Chicago is to train which takes 5h 44m and costs $50 - $160. Alternatively, you can bus, which costs $35 - $130 and takes 7h 53m.

Where does the Winona to Chicago bus arrive?

Winona to Chicago bus services, operated by Jefferson Lines, arrive at Madison station.

Where does the Winona to Chicago train arrive?

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

Can I drive from Winona to Chicago?

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

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

Book your Winona to Chicago train tickets online with Omio.

Where can I stay near Chicago?

There are 1245+ hotels available in Chicago.

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

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

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

Taxi, fly
best
1. Take the taxi from Winona to La-Crosse-Airport-LSE
2. Fly from La Crosse (LSE) to Chicago O'Hare International Airport (ORD)LSE - ORD
2h 40m
$103–313
Bus
cheapest
1. Take the bus from Winona State Univ. to MadisonJefferson 965
2. Take the bus from 250 N. Lake St - Madison UW Campus to W Jackson Blvd, after S Clinton StVan Galder
7h 53m
$38–125
Train (Amtrak)
1. Take the train from Winona to Chicago Union StationEmpire Builder / ...
5h 44m
$50–160
Drive 304.8 mi
1. Drive from Winona to Chicago304.8 mi
4h 56m
$56–81

Winona to Chicago by train (Amtrak)

21Weekly Trains

5h 44mAverage Duration

$50Cheapest Price

See schedules

Questions & Answers

Map of how to get from Winona to Chicago.

Launch map view

Distance: 260.2 mi
Duration: 2h 40m

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

Amtrak operates a train from Winona to Chicago Union Station 3 times a day. Tickets cost $50–160 and the journey takes 5h 44m. Alternatively, you can take a bus from Winona State Univ. to W Jackson Blvd, after S Clinton St via 250 N. Lake St - Madison UW Campus in around 7h 53m.

Airlines

Train operators

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