Cheap train tickets from Chicago to Sheboygan

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Trip Summary

There is one daily train from Chicago to Sheboygan. Traveling by train from Chicago to Sheboygan usually takes 3 hours and 37 minutes, but some trains might arrive slightly earlier or later than scheduled.

Distance: 129 mi (208 km)
Fastest train: 3h 37m
Lowest price: NOK 399.00
Trains per day: 0
Most frequent service: Amtrak
Train lines: 1

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Chicago to Sheboygan Train Schedule

No preview is currently available. Please try another date or search the full schedule.

Train Trip Reviews from Wanderu Customers

Average score for trains from Chicago to Sheboygan (Based on 1 ratings and reviews)

4.0

Pamela

February 5, 2026 - Visiting family

Amtrak

Pros: The train was on time and the connection to my bus was perfect. I use this site every month for a couple of years. Only one time last month something went wrong with the site and it wasn't working. Cons: I wish there were more locations and frequency of trains.

There are several train options that can take you from Chicago to Sheboygan:

Amtrak tickets: NOK 399 one-way

See more details

What is the price of a train ticket from Chicago to Sheboygan?

In the last month, the average price of a train ticket from Chicago to Sheboygan was NOK 418.00. Compared to most train fares, this is an excellent price. Good news! You can find the cheapest tickets if you book your trip at least 11 days prior to the travel date. You’ll likely pay around NOK 95.00 more if you wait to book until the last minute.

Average train ticket prices from Chicago to Sheboygan by travel date

Over the next 30 days, a one-way train trip from Chicago to Sheboygan will cost between NOK 361 and NOK 494. Book in advance to secure the best price in the next few weeks.

Average train ticket prices from Chicago to Sheboygan by month

Ticket prices for the train from Chicago to Sheboygan often fluctuate based on the time of year. For the best prices on this route, book in August when the average ticket price is only NOK 447. If you're thinking of traveling from Chicago to Sheboygan during December, keep in mind that train ticket prices may be higher than usual, with an average price of NOK 494 during this time of year. The best way to score a cheap deal, even in December, is to book your trip well in advance.

Prices as travel date approaches

By booking your train trip from Chicago to Sheboygan on Wanderu at least 11 days ahead of time, you can save about NOK 95.00 on your ticket. Waiting until the last minute means missing out on these savings!

Which train should you take from Chicago to Sheboygan?

Amtrak is the one and only train line which connects Chicago to Sheboygan. Furthermore, there is only one train per day, so you will have to plan your travel around this limited availability. On the other hand, you won't have to spend a ton of time comparing a bunch of possible options.

Train	Daily Trips	Avg. Time	Avg. Price
Amtrak	1	3h 37m	NOK 474.32

Amtrak is the largest passenger railroad service in America, offering daily intercity trains to hundreds of destinations across the contiguous United States, as well as several cities in Canada. Every Amtrak train comes equipped with comfortable seats with extra legroom, as well as several four-seat areas with tables in the middle. In addition, each car has a freshly cleaned restroom, free WiFi and power outlets at every seat. There are also snack bars where you can purchase drinks or food during your journey. On average, there are 1 Amtrak trains from Chicago to Sheboygan every day, as well as 1 trips on the weekends, with prices starting from NOK 399.00.

Frequently asked questions about traveling by train from Chicago to Sheboygan

The distance between Chicago and Sheboygan is approximately 129 miles, or 208 kilometers. The average train journey between these two cities takes 3 hours and 37 minutes, Looking for ways to pass the time? Most trains are equipped with Wi-Fi, which means you can stream music, browse social media or get some work done during your ride. That said, in case your train has a spotty signal, or is among the few without Wi-Fi, we also recommend downloading TV shows and movies to your mobile device in advance of your trip. That way the ride will fly by whatever the Wi-Fi situation.

Distance (mi)

129

Distance (km)

208

Most days, there is only one train which leaves Chicago at 5:08pm and arrives in Sheboygan around 3 hours later.

First train

5:08pm

Last train

5:08pm

Trains from Chicago to Sheboygan are the most crowded on Sunday. Tickets also tend to be more expensive then. If you are looking for a great deal on your train tickets or just want extra room to stretch out, consider traveling on Monday instead, as it tends to be the least crowded day of the week.

Busiest

Sunday

Least crowded

Monday

City Information

Chicago

Known for its innovative architecture, cultural contributions to jazz and house music, and of course that irresistible deep-dish pizza, the many sights and experiences in Chicago make it one of the best urban vacation destinations for millennials and a top destination in Illinois.

You can't beat the views of the city and Lake Michigan from the SkyDeck in the Willis Tower; at over 1,300 feet, this is the highest observation deck in the U.S. Snap that classic selfie with the Bean in Millennium Park, then wander the many museums in nearby Grant Park. Navy Pier is a popular tourist hotspot for its parks, restaurants, and attractions right on Lake Michigan, and baseball fans will find paradise in Wrigleyville, home to the Chicago Cubs' Wrigley Field and sports bars galore.

Chicago's enormous parks offer plentiful opportunities for outdoor activities in gorgeous urban settings. Many companies offer kayak rentals or boat tours on the Chicago River, with special tours running on Saint Patrick's Day, when the entire river is dyed green. When you’re ready to buy some souvenirs from your epic trip, hit the big brand stores on the Magnificent Mile, or shop local in neighborhoods like Andersonville and Wicker Park. And don't miss the chance to laugh until you cry at The Second City comedy theater, famous for launching the careers of comedians like Tina Fey and Stephen Colbert.

Chicago is one of the biggest transportation hubs in the Midwest, and provides easy access to nearby destinations ideal for day trips, as well as international travel from two airports. Thanks to plenty of bus and train stations throughout the city, getting to the Windy City is a breeze.

Station Information

Where is the train station in Chicago?

Main departure station: Union Station

The historic Chicago Union Station is the United States' third busiest train station and a hub for 15 Amtrak train lines with destinations throughout the country. The station also serves bus carriers like Greyhound, Indian Trails and Jefferson Lines, and offers connections to Metra commuter lines. Union Station is also just a quick walk to the nearest Chicago L lines. The current station was built in 1925, to replace the original one dating back to 1881, and today wows visitors with its impressive facade, massive columns, and opulent Great Hall. Located right in downtown and adjacent to the Chicago Loop, Union Station is equipped with many services and amenities, including phone charging stations, shops, and various food and drink options.

All train stations in Chicago:

Union Station

Where is the train station in Sheboygan?

Main arrival station: Sheboygan Transit

Sheboygan has one train station.

All train stations in Sheboygan:

Sheboygan Transit

Need a return trip from Sheboygan to Chicago?

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