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There are 6 ways to get from Chicago to Sheboygan by train, bus, car or plane

Select an option below to see step-by-step directions and to compare ticket prices and travel times in Rome2rio's travel planner.

Recommended option

Train, Amtrak Thruway  •  3 h 29 min

  1. Take the train from Chicago Union Station to Milwaukee Intermodal Station Hiawatha Service
  2. Take the Amtrak Thruway from Milwaukee, WI - Amtrak to Sheboygan, WI 8539 / ...

$38 - $85

Cheapest option

Bus, Amtrak Thruway  •  4 h 20 min

  1. Take the bus from Chicago, Il to Milwaukee, Wi 4712 / ...
  2. Take the Amtrak Thruway from Milwaukee, WI - Amtrak to Sheboygan, WI 8539 / ...

$26 - $61

4 alternative options

Bus  •  5 h 21 min

  1. Take the bus from Chicago, IL - O'Hare International Airport to Milwaukee, WI - Airport Airport Express from Chicago O'hare / ...
  2. Take the bus from Milwaukee, WI - Airport to Sheboygan, WI 104

$39 - $62

Drive  •  2 h 32 min

  1. Drive from Chicago to Sheboygan 147.3 miles

$14 - $21

Fly to Milwaukee, bus  •  5 h 19 min

  1. Fly from Chicago O'Hare (ORD) to Milwaukee (MKE) ORD - MKE
  2. Take the bus from Milwaukee, WI - Airport to Sheboygan, WI

$129 - $397

Fly to Green Bay, bus  •  5 h 4 min

  1. Fly from Chicago O'Hare (ORD) to Green Bay (GRB) ORD - GRB
  2. Take the bus from Green Bay, WI to Sheboygan, WI

$169 - $338

Questions & Answers

The cheapest way to get from Chicago to Sheboygan is to drive which costs $14 - $21 and takes 2 h 32 min.

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The quickest way to get from Chicago to Sheboygan is to drive which costs $14 - $21 and takes 2 h 32 min.

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No, there is no direct bus from Chicago to Sheboygan. However, there are services departing from Chicago, Il and arriving at Sheboygan, WI via Milwaukee, WI - Amtrak. The journey, including transfers, takes approximately 4 h 20 min.

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The distance between Chicago and Sheboygan is 130 miles. The road distance is 147.3 miles.

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The best way to get from Chicago to Sheboygan without a car is to train and Amtrak Thruway which takes 3 h 29 min and costs $35 - $85.

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It takes approximately 3 h 29 min to get from Chicago to Sheboygan, including transfers.

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Chicago to Sheboygan bus services, operated by Greyhound USA, depart from Chicago, Il station.

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The quickest flight from Chicago O'Hare Airport to Milwaukee Airport is the direct flight which takes 47 min.

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Chicago to Sheboygan bus services, operated by Amtrak, arrive at Sheboygan, WI station.

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Yes, the driving distance between Chicago to Sheboygan is 147 miles. It takes approximately 2 h 32 min to drive from Chicago to Sheboygan.

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Map of how to get from Chicago to Sheboygan.
Launch map view
  • Distance: 130.4 miles
  • Duration: 3 h 29 min

What companies run services between Chicago, IL, USA and Sheboygan, WI, USA?

You can take a bus from Chicago to Sheboygan via Milwaukee, Wi and Milwaukee, WI - Amtrak in around 4 h 20 min.

Airlines
United Airlines
Website
united.com
Flights from Chicago O'Hare to Milwaukee
Ave. Duration
53 min
When
Every day
Estimated price
$210 - $490
Flights from Chicago O'Hare to Green Bay
Ave. Duration
1 h 5 min
When
Every day
Estimated price
$240 - $800
American Airlines
Website
aa.com
Flights from Chicago O'Hare to Milwaukee
Ave. Duration
53 min
When
Every day
Estimated price
$180 - $490
Flights from Chicago O'Hare to Green Bay
Ave. Duration
59 min
When
Every day
Estimated price
$260 - $500
Train operators
Amtrak

Amtrak is a rail service that connects the US and three Canadian provinces. Covering 21,000 route miles (34,000km) Amtrak operates more than 300 trains daily. These medium and long distance intercity services operate at speeds of up to 240km/h, to more than 500 destinations. Founded in 1971, it is based in Washington, D.C. and offers four classes of travel: First Class, Sleeper, Business and Coach. Ticket fares are divided into five subclasses: Saver, Value, Flexible, Business and Premium. Amtrak trains are known for their wide seats, plug-in power, big windows and storage capabilities.

Rome2rio's guide to Amtrak
Contact Details
Phone
+1 215-856-7924
Website
amtrak.com
Train from Chicago Union Station to Milwaukee Intermodal Station
Ave. Duration
1 h 29 min
Frequency
Every 4 hours
Estimated price
$28 - $60
Website
amtrak.com
Coach Seat
$28 - $45
Flexi Coach Seat
$50 - $75
Business Coach Seat
$40 - $60
Room
$150 - $220
Bus operators
Amtrak

Amtrak is a rail service that connects the US and three Canadian provinces. Covering 21,000 route miles (34,000km) Amtrak operates more than 300 trains daily. These medium and long distance intercity services operate at speeds of up to 240km/h, to more than 500 destinations. Founded in 1971, it is based in Washington, D.C. and offers four classes of travel: First Class, Sleeper, Business and Coach. Ticket fares are divided into five subclasses: Saver, Value, Flexible, Business and Premium. Amtrak trains are known for their wide seats, plug-in power, big windows and storage capabilities.

Rome2rio's guide to Amtrak
Contact Details
Phone
+1 215-856-7924
Website
amtrak.com
Bus from Milwaukee, WI - Amtrak to Sheboygan, WI
Ave. Duration
1 h
Frequency
3 times a day
Website
amtrak.com
Indian Trails
Phone
+1 800-292-3831
Website
indiantrails.com
Bus from Milwaukee to Sheboygan Transit
Ave. Duration
1 h
Frequency
Once daily
Estimated price
$10 - $14
Schedules at
indiantrails.com
Book at
webstore.indiantrails.com
Jefferson Lines
Phone
800-451-5333
Email
info@jeffersonlines.com
Website
jeffersonlines.com
Bus from Milwaukee to Sheboygan, WI
Ave. Duration
1 h
Frequency
Once daily
Estimated price
$18 - $26
Book at
jeffersonlines.com
Bus from Green Bay, WI to Sheboygan, WI
Ave. Duration
1 h 15 min
Frequency
Once daily
Estimated price
$20 - $28
Book at
jeffersonlines.com
Lamers Bus Lines
Phone
+1 800-236-1240
Website
golamers.com
Bus from Milwaukee, WI to Sheboygan, WI
Ave. Duration
1 h 20 min
Frequency
4 times a week
Estimated price
$16 - $20
Schedules at
golamers.com
Book at
webstore.golamers.com
Bus from Milwaukee, WI - Airport to Sheboygan, WI
Ave. Duration
1 h 50 min
Frequency
4 times a week
Estimated price
$17 - $22
Schedules at
golamers.com
Book at
webstore.golamers.com
Greyhound USA

Greyhound is a leading bus company based in Dallas, Texas, serving over 3800 destinations across North America, Mexico and Canada. Greyhound carries around 18 million passengers a year who travel 5.4 billion miles (8.6 billion km) a year on their fleet of around 1700 vehicles. For travel flexibility, you can board or get off a Greyhound bus at official Greyhound stations, partner stations and curbside stops. There are around 230 Greyhound stations across the US where you can both catch your bus and buy tickets, that are also available on the official website and via the mobile app.

Rome2rio's guide to Greyhound USA
Contact Details
Phone
+1 214-849-8100/1-800-231-2222
Email
ifsr@greyhound.com
Website
greyhound.com
Bus from Chicago, Il to Milwaukee, Wi
Ave. Duration
2 h 20 min
Frequency
Every 4 hours
Estimated price
$15 - $35
Website
greyhound.com
Economy
$15 - $23
Flexible
$28 - $35
Coach USA

Want to know more about travelling around United States

Rome2rio's Travel Guide series provide vital information for the global traveller. Filled with useful and timely travel information, the guides answer all the hard questions - such as 'How do I buy a ticket?', 'Should I book online before I travel? ', 'How much should I expect to pay?', 'Do the trains and buses have Wifi?' - to help you get the most out of your next trip.

More Questions & Answers

American Airlines and United Airlines offer flights from Chicago O'Hare Airport to Milwaukee Airport.

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There are 17+ hotels available in Sheboygan. Prices start at $65 USD per night.

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The best way to get from Chicago to Chicago O'Hare Airport is to subway which takes 42 min and costs $2 - $5.

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