$50 Cheap flights to Sheboygan County

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Top places to visit in Sheboygan County

A lighthouse at sunset with a colorful sky and calm water.
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Sheboygan

Sheboygan
A house by a calm lake with autumn foliage and a clear sky.
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Elkhart Lake

Elkhart Lake
A winding wooden boardwalk through a grassy field with a pine tree and a distant view of a body of water and mountains.
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Kohler

Kohler

Cheap flights to Sheboygan County from $50 One Way, $97 Round Trip

$97 return flights and $50 one-way flights to Sheboygan County were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Fri, Sep 18 - Mon, Sep 21
BNA
Nashville
ATW
Appleton
$97 Roundtrip, found 8 hours ago
$97
Roundtrip
found 8 hours ago
Select Allegiant Air flight, departing Fri, Sep 18 from Nashville to Appleton, returning Mon, Sep 21, priced at $97 found 8 hours ago
Sat, Aug 29 - Mon, Aug 31
SFB
Orlando
ATW
Appleton
$102 Roundtrip, found 4 hours ago
$102
Roundtrip
found 4 hours ago
Select Allegiant Air flight, departing Sat, Aug 29 from Orlando to Appleton, returning Mon, Aug 31, priced at $102 found 4 hours ago
Thu, Sep 10 - Thu, Sep 17
MCO
Orlando
ATW
Appleton
$106 Roundtrip, found 2 days ago
$106
Roundtrip
found 2 days ago
Select Allegiant Air flight, departing Thu, Sep 10 from Orlando to Appleton, returning Thu, Sep 17, priced at $106 found 2 days ago
Fri, Oct 2 - Mon, Oct 5
DEN
Denver
ATW
Appleton
$114 Roundtrip, found 3 hours ago
$114
Roundtrip
found 3 hours ago
Select Allegiant Air flight, departing Fri, Oct 2 from Denver to Appleton, returning Mon, Oct 5, priced at $114 found 3 hours ago
Tue, Sep 15 - Tue, Sep 22
PGD
Punta Gorda
ATW
Appleton
$120 Roundtrip, found 20 hours ago
$120
Roundtrip
found 20 hours ago
Select Allegiant Air flight, departing Tue, Sep 15 from Punta Gorda to Appleton, returning Tue, Sep 22, priced at $120 found 20 hours ago
Mon, Aug 17 - Mon, Aug 24
FLL
Fort Lauderdale
ATW
Appleton
$124 Roundtrip, found 4 hours ago
$124
Roundtrip
found 4 hours ago
Select Allegiant Air flight, departing Mon, Aug 17 from Fort Lauderdale to Appleton, returning Mon, Aug 24, priced at $124 found 4 hours ago

Deals For This Weekend's Flights

OriginDestinationTravel DatesFlights From*
DENAppletonAugust 7 to August 10$348
DTWAppletonAugust 8 to August 8$706
*Prices include taxes and fees

Find The Perfect Hotel For After Your Flight

Score Epic Sheboygan County Accommodation Deals

Watershed Hotel

Watershed Hotel

3 out of 5
838 N 15th St Sheboygan WI
Fully refundableReserve now, pay when you stay
$185 nightly
The price is $210 total per night from Aug 2 to Aug 3
$210 total
Aug 2 - Aug 3
Total with taxes and fees
Book a stay at this business-friendly hotel in Sheboygan. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
9.8/10 Exceptional! (611 reviews)
"We really enjoyed our stay. The rooms are clean, modern, and spacious with great views of the river. Staff were friendly and helpful."

Reviewed on Aug 1, 2026

Opens in a new windowWatershed Hotel
Grandstay Residential Suites Hotel - Sheboygan

Grandstay Residential Suites Hotel - Sheboygan

2.5 out of 5
708 Niagara Avenue Sheboygan WI
Fully refundableReserve now, pay when you stay
$169 nightly
The price is $192 total per night from Sep 1 to Sep 2
$192 total
Sep 1 - Sep 2
Total with taxes and fees
Book a stay at this business-friendly aparthotel in Sheboygan. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the ...
8.6/10 Excellent! (1,062 reviews)
"Nice hotel in a great location. Rooms are big and comfortable!"

Reviewed on Jul 29, 2026

Opens in a new windowGrandstay Residential Suites Hotel - Sheboygan
The American Club

The American Club

5 out of 5
419 Highland Drive Kohler WI
Fully refundable
$585 nightly
The price is $646 total per night from Aug 30 to Aug 31
$646 total
Aug 30 - Aug 31
Total with taxes and fees
Book a stay at this luxury hotel in Kohler. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular ...
Opens in a new windowThe American Club
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AmericInn by Wyndham Sheboygan

AmericInn by Wyndham Sheboygan

3 out of 5
3664 S Taylor Dr Sheboygan WI
Fully refundableReserve now, pay when you stay
$93 nightly
The price is $105 total per night from Aug 23 to Aug 24
$105 total
Aug 23 - Aug 24
Total with taxes and fees
Book a stay at this business-friendly hotel in Sheboygan. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
8.4/10 Very Good! (1,000 reviews)
"Staff was great. Room sink didn't drain hardly at all. Pretty limited on bath towels for a 2 night stay. Overall not bad."

Reviewed on Jul 29, 2026

Opens in a new windowAmericInn by Wyndham Sheboygan
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Need a Car For After Your Flight?

Economy

Chevrolet Spark
  • 4 people
Chevrolet Spark
Economy Chevrolet Spark

Compact

Ford Focus
  • 4 people
Ford Focus
Compact Ford Focus

Midsize

Toyota Corolla
  • 5 people
Toyota Corolla
Midsize Toyota Corolla

SUV

Jeep Compass
  • 5 people
Jeep Compass
SUV Jeep Compass

Sheboygan County

Why search for low cost fares on your flights to Sheboygan County when Orbitz offers the guaranteed lowest prices on foreign and domestic flights? When you travel with Orbitz you can benefit from:

Bargain Flights to Sheboygan County

Orbitz offers massive discounts and substantial last-minute savings on your Sheboygan County flights. Orbitz ensures that you can find, plan and reserve your flights any destination with ease, all while enjoying the guaranteed lowest prices available anywhere.

Cutting-Edge Mobile Tools to Keep You In The Know

Orbitz sends you free alerts and updates on your Sheboygan County flight wherever you are in the world. Once you have downloaded the free app for your iPhone, Android, or iPad, you can review or alter any travel plans that you have made or even book a future flight for business or pleasure. If you need to reserve a hotel room when booking your flight, you will find exclusive deals on our mobile site.

Frequent Flyer Program Enrolment

Orbitz finds you the lowest fares, but you can still add your miles to your frequent flyer program to earn miles or points on selected flights to Sheboygan County. When making your booking, reference your frequent flyer number to receive discounts in the future.

Outstanding Customer Service

Orbitz values your business and wants to ensure that all of your flights are as easy as possible to book. If you have booked a flight to Sheboygan County but need to cancel it, you may be able to do so online. If you have any questions or need help, the dedicated Orbitz customer service team is always standing by.

Frequently asked questions

Which airlines fly to Sheboygan County?
Book an airfare with one of the 12 airlines that operate services to O'Hare Intl. Airport (ORD) and gear up for thrilling new adventures. This popular airport is a major entry point for exploring Sheboygan County. When you're ready to tick off this region, these leading carriers will take you there:

  • United Airlines - 612 flights to Sheboygan County per month
  • American Airlines - 339 flights to Sheboygan County per month
  • Air Canada - 190 flights to Sheboygan County per month

How much is a flight to Sheboygan County?
Return flight prices dipped as low as $97 this past week to Sheboygan County, and peaked at $706. Several lucky travelers journeying out of Nashville (BNA) managed to land one-way tickets from just $50.
How to book the cheapest flight to Sheboygan County?
Landing cheap flights to Sheboygan County is as easy as booking your ticket with Orbitz. But if you're eager to make sure you're walking away with the best flight deals around, here are some suggestions worth following:

  • Consider departing from or arriving at other airports to cut costs. Enter your preferred departure and arrival points in the form fields, then select the 'Nearby airports' function below. It will list the available options.
  • Also, click on the 'Show flexible dates' link to bring up the fares on days either side of your chosen departure. It's possible to find cheaper flight deals if your travel dates are flexible.
  • You can also select the 'Show options' link to filter results for your preferred carrier, seating class, and nonstop and refundable flights. Under 'Sort & Filter' to the left, you can even choose the time of day you'd like to fly.
  • The early bird gets the most rewarding deals, so purchase your seats once you've settled on your travel dates. The most affordable fares go like hotcakes and prices normally climb as the departure date nears.
  • Save big on your vacation by bundling your hotel, flights and car rentals into an Orbitz package deal. Your credit card will thank you.
  • If you can, avoid flying during the busy season. Airfares are often at their most expensive during summer, school breaks and around other vacation times like Easter and Christmas.

What is the best time to book a flight to Sheboygan County?
If your schedule allows, purchase your seats to Sheboygan County in January. This is the best month to reserve low airfares, closely followed by February and August. With a little planning, you're guaranteed to find a cheap flight with Orbitz.
What day of the week is the cheapest to book a flight to Sheboygan County?
To score a fantastic flight deal, book on a Tuesday, Wednesday or Saturday. Typically, these are the cheapest days to purchase flights to Sheboygan County.
What is the cheapest day of the week to fly to Sheboygan County?
Everybody enjoys saving money, so we recommend leaving earlier in the week for cheap flights to Sheboygan County. Orbitz data from 2020 shows you can snap up the best prices on flights taking off on Mondays. Tuesdays are the next most affordable day, while Saturdays are likely to cost a bundle. Many passengers like to travel on weekends, so leave those Saturdays for binge-watching your favorite TV shows.
What is the cheapest month to fly to Sheboygan County?
To secure cheap flights to Sheboygan County, pack your bags and travel in August. Orbitz data shows that this is generally a great month to save on your airfare. If you're hoping to fly to Sheboygan County in June, keep in mind that this is the most expensive time to take a trip.
Which airlines allow free cancellation?
We know that plans change and flexibility is important. That's why you can easily search for flights that include free cancellation and no change fees on Orbitz. Just click on "Filter by flexible change policies" and we'll find you fares more flexible than a lollipop left in the sun!
What do I need for the flight to Sheboygan County?
Nothing beats jetting off to a cool new place, but it's smart to be prepared. These practical tips will help get your trip off to a great start:

  • Your travel documents are the most important things you'll need to have with you on your flight to Sheboygan County. To avoid any problems during check-in, make sure that the name on your ticket matches your government-issued ID.
  • Make time fly by even quicker on your short flight by packing the right things. Think tasty snacks, a water bottle and entertainment. If you'd like your journey to Sheboygan County to pass nice and peacefully, squeeze some headphones or earplugs into your carry-on bag as well.
  • It can get very cool on the plane. If you don't like the idea of shivering your way through the flight, wear an extra layer of clothes.

How do I get cheap first-class/business deals to Sheboygan County?
Smart travelers know how to find business or first-class airfares to Sheboygan County that don't cost an arm and a leg. Follow in their footsteps with these handy hints:

  • Flexibility isn't just for your yoga class. Avoid locking in your travel dates so you can snap up more affordable airfares when a sale comes along.
  • Budget airlines offer business-class seats at a fraction of the normal price. Skip the full-service carriers and fly with one these cheaper options.
  • Make the most of your airline's loyalty scheme and upgrade your seat. You can also bid for an upgrade in online auctions.

What is the best time to go to Sheboygan County?
If you'd like to experience the unique vibe of Sheboygan County in the peak season, April, May and July are the prime months to visit. June 20 marks the start of summertime in the Northern Hemisphere and is a perfect time to travel if you delight in being outside. Around this time of year, average daily temperatures typically range from 60 ºF to 75 ºF.

Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.