1map logoGo to main page

Sheboygan, WI, USA to Chicago, IL, USA from $9: 8 ways by bus, train, flight or car

Compare Travel Options and Prices

from
Sheboygan, United States of America
to
Chicago, United States of America

How to Get from Sheboygan to Chicago: Cheapest, Fastest and Best Way

1Map provides directions to cities, towns, landmarks, attractions, and addresses worldwide, offering thousands of multi-modal routes to easily get you from point A to point B.

$9 - OtherBest price
237 kmDistance
2h 35m Fastest

Compare Train, Bus, Flight, and Driving Options

Get detailed, step-by-step directions below for your trip from Sheboygan to Chicago with 1Map travel planner. Easily compare ticket prices, explore various transport options, and find the best routes for a seamless and cost-effective travel experience.

Company
Greyhound USA
Bus
Average Duration
3h 
Estimated price
$16-55
Recommended
Company
Various
Bus
Train
Average Duration
3h  29m
Estimated price
$9-103
Cheapest
route map
Distance: 237 km
Duration: 2h 35m

See more options

Company
Various
Drive
Train
Average Duration
3h  38m
Estimated price
$9-122
Company
Various
Drive
Average Duration
2h  35m
Estimated price
$26-40
Company
Various
Bus
Average Duration
5h  13m
Estimated price
$30-61
Company
Various
Bus
Plane
Average Duration
4h  28m
Estimated price
$90-162
Company
Various
Drive
Plane
Average Duration
3h  9m
Estimated price
$99-161
Company
Various
Drive
Plane
Average Duration
3h  33m
Estimated price
$160-406
Browse car rentalsExplore flights

Traveling From Sheboygan to Chicago

The journey from Sheboygan to Chicago offers a delightful contrast between the serene shores of Lake Michigan and the vibrant, bustling energy of urban life.

Best Neighborhoods in Chicago

Chicago's neighborhoods each offer a distinct blend of culture and attractions.

Wicker Park
• Trendy boutiques and vibrant street art abound.
• A hotspot for eclectic dining experiences.
Lincoln Park
• Homes the beautiful Lincoln Park Zoo and lakefront.
• Offers sprawling parks and scenic walking paths.
The Loop
• Central business district with iconic skyscrapers.
• Rich in cultural attractions like theaters and museums.

Best Times To Visit Chicago's Attractions

Maximize your Chicago experience by timing your visits to popular attractions.

Millennium Park
Early mornings or weekdays are ideal for fewer crowds and stunning views.
The Art Institute of Chicago
Visit on Tuesday or Wednesday afternoons for a quieter art exploration.
Navy Pier
Go early in the day or during the off-season to enjoy shorter lines.

Chicago Weather: What to Expect Year-Round

Chicago experiences distinct seasons, with cold winters and warm summers, making the spring and fall the best times to visit for pleasant weather. Understanding the climate helps you pack appropriately and plan activities that align with your travel preferences.

Dining Recommendation in Chicago

Indulge in a slice of deep-dish pizza at Giordano's, where the savory layers of cheese and rich tomato sauce create a comforting culinary experience that stands apart from Sheboygan's more laid-back fare. The lively atmosphere and use of locally sourced ingredients enhance the excitement of dining in a city renowned for its vibrant food scene.

Sheboygan - Chicago operators

Explore transport companies operating between Sheboygan and Chicago, with prices starting at . These companies offer competitive pricing, flexible schedules, and comfortable travel experiences.

Bus Show bus routes
Contact phone
+1 214-849-8100
Website
https://www.greyhound.com/

Bus from Sheboygan to Chicago Bus Station

Average Duration
3h
Estimated price
$16-55

Bus from Sheboygan, WI to Milwaukee

Average Duration
1h
Estimated price
$555-1655
Contact phone
+1 800-292-3831
Website
https://www.indiantrails.com/

Bus from Sheboygan, WI to Milwaukee, WI

Average Duration
1h
Estimated price
$556-553
Train Show train routes
Contact phone
+1 800-872-7245
Website
https://www.amtrak.com/home.html

Train from Milwaukee to Chicago Union Station

Average Duration
1h 29m
Estimated price
$165-166

Train from Sheboygan Amtrak Bus Stop to Milwaukee

Average Duration
1h
Estimated price
$0-0
Contact phone
+1 800-872-7245
Website
http://www.amtrak.com

Train from Sheboygan, WI to Milwaukee

Average Duration
1h 5m
Estimated price
$555-40
Plane Show flights
Website
united.com

Plane from Appleton Airport to Chicago O'Hare Airport

Average Duration
1h 16m
Estimated price
$163-164

Plane from Green Bay Airport to Chicago O'Hare Airport

Average Duration
1h 17m
Estimated price
$163-550
Website
aa.com

Plane from Appleton Airport to Chicago O'Hare Airport

Average Duration
1h 16m
Estimated price
$163-400

Plane from Green Bay Airport to Chicago O'Hare Airport

Average Duration
1h 20m
Estimated price
$163-550

Sheboygan to Chicago: Overview of Bus, Train, Flight, and Car Trips

Traveling between Sheboygan and Chicago offers a variety of convenient options to suit your preferences, schedule, and budget. Whether you prioritize affordability, speed, or comfort, you’re sure to find the perfect way to travel without compromising on quality or convenience.

🚗 Embark on a scenic road trip from Sheboygan to Chicago, covering a distance of 147 miles in approximately 2 hours and 35 minutes. 💰 Enjoy flexibility in pricing, with car travel costs ranging from $26 to $40 for the journey between these two vibrant cities.
Average price
$26 - $40
🚆 Hop on a train in Sheboygan and enjoy a scenic journey to Chicago, lasting approximately 3 hours and 38 minutes. Take in the views as you travel through the picturesque Midwest landscapes. 💰 Ticket prices for the train between Sheboygan and Chicago range from as low as $9 to $122, offering budget-friendly options for travelers. Choose a ticket that suits your schedule and budget for a convenient and affordable transportation option.
🛫 Flying from Sheboygan to Chicago is convenient with direct flights from Appleton Airport to Chicago O'Hare Airport. The quickest flight on this route takes just 1 hour and 16 minutes.
Departure Point
Appleton Airport
Arrival Point
Chicago O'Hare Airport
🚌 Hop on a direct Greyhound bus departing from Sheboygan and arriving at Chicago Bus Station, operating five times a week. The journey from Sheboygan to Chicago takes approximately 3 hours. 🛣️ Route 1 involves a transfer, with the first step being a bus towards Milwaukee for about 1 hour. Then, catch a bus from Milwaukee to Chicago for about 1 hour and 45 minutes. Total travel time is 3 hours and 25 minutes for the 142-mile journey. 🚌 Route 2 offers a direct bus service from Sheboygan to Chicago Bus Station, taking around 3 hours for the 149-mile trip. Enjoy a convenient and budget-friendly way to travel between these two Midwest cities by bus.
Departure Point
Sheboygan station
Arrival Point
Chicago Bus Station

Frequently asked questions

Find out more about the route from Sheboygan to Chicago.

Or choose the category:
The cheapest way to travel from Sheboygan to Chicago is by bus. There are several bus companies that operate this route, offering fares ranging from $16 to $55. The journey takes approximately 3 hours, depending on traffic and other factors. It is recommended to compare prices and schedules from different bus operators to find the best option for your budget.
The fastest way to travel from Sheboygan to Chicago is by driving. The journey takes approximately 2 hours and 35 minutes, depending on traffic conditions. The estimated cost of fuel for this trip ranges from $26 to $40, considering the distance of around 150 miles between the two cities. It is recommended to check for real-time traffic updates and plan the journey accordingly for a smoother and more efficient drive.
To travel from Sheboygan to Chicago without a car, the most convenient option is to take a bus. There are several bus companies that operate between the two cities, with fares ranging from $16 to $55. The journey takes approximately 3 hours, depending on traffic conditions. Buses are a cost-effective and hassle-free way to travel, offering comfortable seating and amenities such as WiFi.
The bus journey from Sheboygan to Chicago takes approximately 3 hours, including transfers. The bus service operates five times a week, providing regular transportation between the two cities. This time frame offers a convenient and time-efficient option for travelers looking to reach Chicago from Sheboygan.
There are numerous accommodation options available near Chicago. With over 1116 hotels to choose from, travelers can find a range of options to suit their needs and budget. Prices for hotels in Chicago start at $58 per night, offering a variety of choices for every traveler. It is advisable to book in advance to secure the best rates and availability.
Yes, you can drive from Sheboygan to Chicago. The driving distance is approximately 147 miles, and it takes about 2 hours and 35 minutes to complete the journey. The route typically involves taking I-43 South and I-94 West. However, please note that driving conditions may vary, so it's always a good idea to check for any traffic or road updates before starting your trip.
Yes, there is a direct bus between Sheboygan and Chicago. The bus service operates five times a week, specifically on Mondays, Thursdays, Fridays, Saturdays, and Sundays. The bus departs from Sheboygan and arrives at the Chicago Bus Station. The journey takes approximately 3 hours.
To catch the bus from Sheboygan to Chicago you can go to the Sheboygan station. Greyhound USA operates the bus services from this station. You can check the Greyhound website or contact their customer service for more specific information on the departure location and schedule.
The bus from Sheboygan to Chicago arrives at the Chicago Bus Station. Greyhound USA operates the bus services between these two cities. The Chicago Bus Station is located in the heart of downtown Chicago, making it convenient for travelers to explore the city's attractions and connect to other forms of transportation. The station offers amenities such as restrooms, seating areas, and ticketing services to ensure a smooth arrival experience for passengers.
American Airlines and United Airlines are the two main airlines that provide flights between Sheboygan and Chicago. These flights typically depart from Milwaukee Airport and arrive at Chicago O'Hare Airport. It is recommended to check with the respective airlines for current flight schedules and prices.
The fastest way to get from Sheboygan to Chicago by plane is to fly from Milwaukee Airport to Chicago O'Hare Airport. The quickest flight is a direct flight and takes approximately 1 hour and 2 minutes. Airlines such as American Airlines and United Airlines offer flights from Milwaukee Airport to Chicago O'Hare Airport, providing convenient options for travelers seeking a fast journey between the two cities. With this option, travelers can save time and arrive in Chicago quickly.
The flight from Sheboygan to Chicago is approximately 1 hour and 2 minutes. This is the shortest and most convenient way to travel between the two cities. The flight is direct, departing from Milwaukee Airport and arriving at Chicago O'Hare Airport. It is recommended to arrive at the airport at least 1 hour in advance for check-in and security procedures.
The cost of a bus ticket from Sheboygan to Chicago ranges from $16 to $55. The exact price may depend on factors such as the time of day, day of the week, and whether it is a one-way or round-trip ticket. It is recommended to check with different bus operators for the best available fares and to book in advance to secure the lowest prices.
The cost to drive from Sheboygan to Chicago will depend on factors such as fuel prices and the efficiency of your vehicle. On average, it can cost between $26 and $40 for the round trip, considering a distance of approximately 145 miles and an average fuel consumption of 25 miles per gallon. Additionally, keep in mind that tolls may also apply along the route, so it's a good idea to budget for those as well.

Trips to Chicago