Cheap train tickets from Chicago to Sheboygan
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Chicago to Sheboygan Train Schedule
Trip Summary
There are usually 2 daily train trips available from Chicago to Sheboygan. Traveling by train from Chicago to Sheboygan usually takes 3 hours and 24 minutes, but the fastest Amtrak train can make the trip in 3 hours and 10 minutes.
| Distance | 129 mi (208 km) |
| Fastest train | 3h 10m |
| Lowest price | HRK 261.93 |
| Most frequent service | Amtrak |
| Train lines | 1 |

What is the price of a train ticket from Chicago to Sheboygan?
In the last 30 days, the average cost of a train ticket from Chicago to Sheboygan was HRK 284.85. At this price, taking the train is the cheap and easy way to go. You have the best chances of scoring the cheapest ticket to Sheboygan if you book your train tickets at least 26 days in advance. Waiting to purchase until the day of your trip could end up costing you an extra HRK 47.93.
Monthly avg. prices
Prices as travel date approaches
The average price of train tickets from Chicago to Sheboygan is pretty stable year-round. However, we still suggest buying your train tickets at least 48 hours prior to departure to avoid unexpected price hikes and the possibility of the train being sold out.
Which train should you take from Chicago to Sheboygan?
Amtrak is the one and only train line which connects Chicago to Sheboygan. The schedule is relatively limited as the train only runs twice a day.
| Train | Daily Trips | Avg. Time | Avg. Price |
|---|---|---|---|
| Amtrak | 2 | 3h 25m | HRK 322.37 |
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 2 Amtrak trains from Chicago to Sheboygan every day, as well as 2 trips on the weekends, with prices starting from HRK 262.
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 24 minutes, although the absolute fastest you could get there is 3 hours and 10 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.
Trains departing from Chicago to Sheboygan tend to have the most passengers on Saturday. With higher demand ticket prices also tend to be higher on Saturday. If you are trying to snag a cheap train tickets or just want an emptier train you'll have better luck by booking travel departing on Monday as the least number of people tend to travel then.
The earliest train departs Chicago at 8:00am while the last train of the day leaves at 5:00pm. To see all scheduled departure times, use the search function on this page to get the full schedule for your specific travel dates.
Trains leave the station in Chicago twice a day, so there are a couple of options depending on your preferred travel time. However, there are no direct trains. This means that you will need to disembark from your original train and board a connecting train at some point during your journey. You will need to remember to bring your carry-on luggage with you when you change trains. Depending on the carrier's policy, you may also be responsible for transferring your own checked baggage.
You can also take a train for your return trip from Sheboygan to Chicago.
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?

Image credit: Jeramey Jannene
Link to image attribution
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
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