The cheapest and fastest trains from Sheboygan, WI to Chicago, IL
Cheapest price
$53
Average price
$53
Fastest journey
5 h 19 m
Average duration
5 h 19 m
Trains per day
1
Distance
211 km
The best way to find a cheap train ticket from Sheboygan, WI to Chicago, IL is to book your journey as far in advance as possible and to avoid traveling at rush hour.
The average ticket from Sheboygan, WI to Chicago, IL will cost around $53 if you buy it on the day, but the cheapest tickets can be found for only $53.
Of the 1 trains that leave Sheboygan, WI for Chicago, IL on Wed, Feb 25, 1 travel direct so it’s quite easy to avoid journeys where you’ll have to change along the way.
On Wed, Feb 25 the direct trains cover the 211 km distance in an average of 5 h 19 m but if you time it right, some trains will get you there in just 5 h 19 m .
On Wed, Feb 25 the slowest trains will take 5 h 19 m and usually involve a change or two along the way, but you might be able to save a few pennies if you’re on a budget.


Travel Information
Compare bus, train, and flight for Sheboygan, WI to Chicago, IL
Omio recommends booking the train as it is the most popular option from Sheboygan, WI to Chicago, IL among Omio's users. If you are prioritising price take the train with prices starting from $49. For those with little time consider booking a flight which can get you there in 1h 15m. The ticket price range depends on the travel mode: a train costs an average of $49, and a flight costs an average of $127.
Distance: 131 miles (211 km)
Compare train with
Most popular Train | Bus | Flight |
|---|---|---|
$54 Average price Cheapest | $59 Average price | $197 Average price |
3h 6m Average total duration 2h 36m Onboard + 30m Additional time* | 3h 50m Average total duration 3h 20m Onboard + 30m Additional time* | 4h 15m Average total duration Fastest 1h 15m Onboard + 3h 0m Additional time* |
Direct Options | Direct Options | Direct Options |
Live departures
Sheboygan, WI to Chicago, IL train times
The table below shows live departures for Sheboygan, WI to Chicago, IL trains for tomorrow, Wednesday, February 25. You can also manually refresh the results below to see updated train journeys.
| Provider | Departs | Duration | Arrives | Transfers | Tickets | |
|---|---|---|---|---|---|---|
![]() | 1:10 PM Sheboygan, WI | 5h19 | 6:29 PM Chicago, IL | 0 transfersDirect | ||
This is the last train of the day. | ||||||
Find all the dates and times for this journey
Compare prices and tickets Sheboygan, WI to Chicago, IL by bus, train, or flight
Compare bus, train, and flight prices over the next three weeks. See the best deals at a glance, find the lowest fares, and choose the option that fits your budget.
Feb 25
Feb 26
Feb 27
Feb 28
Mar 01
Mar 02
Mar 03
Journey information
Overview: Train from Sheboygan, WI to Chicago, IL
Trains from Sheboygan, WI to Chicago, IL run on average 5 times per day, taking around 2h 36m. Cheap train tickets for this journey start at $49 (€39) if you book in advance.
The earliest train runs at 06:35, the last at 17:08. The fastest train covers the 131 miles (211 km) distance in 4h 44m.
Distance 131 miles (211 km) |
Average train duration 2h 36m |
Cheapest ticket price $49 (€39) |
Trains per day 5 |
Fastest train 4h 44m |
First train 06:35 |
Last train 17:08 |
Train companies: Amtrak from Sheboygan, WI to Chicago, IL trainsAmtrak trains will get you between Sheboygan, WI and Chicago, IL from $49 (€39). With over 1000 travel companies on Omio, you can find the best train times and tickets for your trip.
Amtrak
FAQs: Trains from Sheboygan, WI to Chicago, IL
Find answers to the most common questions about traveling from Sheboygan, WI to Chicago, IL by train. From journey times and ticket prices to direct connections, first and last departures, and even whether the route is scenic, our FAQs cover everything you need to plan your trip. Whether you’re looking for the fastest train, the cheapest option, or tips for making the most of your visit at Chicago, IL, this guide helps you travel smarter and with confidence.

popular train stations
Popular train stations from Sheboygan, WI to Chicago, IL
- 5:00 AM - 12:00 AM Monday - Sunday
- Free
- The car park is open 7 days a week from 5:00 a.m. to 12:00 a.m. Departures can be made outside of opening hours. Access via Canal Street.
- The Chicago Firehouse Restaurant
- Lou Mitchell's
- Outside the main entrance.
- Elevators, ramps, restrooms.
- $1
- The Kimpton Gray Hotel
- JW Marriott Chicago
- W Chicago - City Center
- Located in the main hall
- Located in the main hall
- Avis
- Budget
- Enterprise
- Located in the main hall
- Free
- Hall 1: main entrance, Amtrak services
- Hall 2: Metra services
- Hall 3: food court and retail shops
- Bus: Several lines available
- CTA: Blue Line, Pink Line
More options for your journey from Sheboygan, WI to Chicago, IL
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