Is there a direct train?

No, you must drive to Milwaukee first to catch the Amtrak.

How long is the drive?

It takes about 3 hours, but traffic can add significant time.

Yes, expect tolls on the Illinois portion of I-94.

Is it better to take the train?

The train is more relaxing and avoids Chicago traffic.

Where does the train arrive?

It arrives at Chicago Union Station.

Sheboygan

Chicago

Train Driving

Sheboygan to Chicago

Updated: 28 May 2026

The journey from Sheboygan to Chicago covers approximately 230 kilometers. You can drive via I-43 and I-94, which takes about 3 hours depending on traffic. Alternatively, you can drive to Milwaukee and take the Amtrak Hiawatha train for a stress-free arrival in downtown Chicago. Chicago is a major hub with extensive public transit options. This route is popular for both business and leisure travelers.

Total Distance: 230 km driving distance, 215 km air distance.

Fastest Way

Driving is the fastest method, taking approximately 3 hours, though traffic can vary.

Cheapest Way

Driving is generally cheaper if you are traveling with more than one person.

Compare Sheboygan to Chicago Routes

	Train Connecting	Driving Direct
Duration	3 hours 30 mins	3 hours
Avg Price	$30-$50	$40-$50 in fuel
Operator	Amtrak Hiawatha	Personal Vehicle
Route	Drive to Milwaukee Intermodal, then train to Union Station	I-43 South to I-94 East
Tip	Book Amtrak tickets in advance to save money.	Expect heavy traffic entering Chicago; use the I-90/94 express lanes if available.

Travel Tips

Traffic
Avoid driving into Chicago during weekday rush hours (7-9 AM and 4-6 PM).
Parking
Parking in downtown Chicago is very expensive; use public transit or pre-booked garages.
Public Transit
Use the CTA 'L' train system to get around the city efficiently.
Safety
Stay aware of your surroundings in crowded tourist areas.
Booking
If taking the train, arrive at the Milwaukee station 30 minutes before departure.

Safety Tips

Driving
Chicago traffic is aggressive; stay alert and follow lane markings.
Personal Safety
Keep your belongings secure in public spaces and on public transit.
Weather
Chicago can be very windy; dress appropriately for the lakefront.
Emergency
Dial 911 for any emergencies in the city.