$56 Cheap flights to Sheboygan County

Earn rewards on top of your airline miles with Orbitz Rewards

Many airlines offer flexible change policies

Sign up to receive text alerts about your trip

Top places to visit in Sheboygan County

A red lighthouse amidst rough seas with waves crashing against a pier.
FlightsFlights
FlightsFlights

Sheboygan

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

Elkhart Lake

Elkhart Lake
A landscape with birch trees, a clear blue sky, and a distant horizon.
FlightsFlights
FlightsFlights

Kohler

Kohler

Cheap flights to Sheboygan County from $56 One Way, $91 Round Trip

$91 return flights and $56 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, Dec 4 - Mon, Dec 7
BNA
Nashville
ATW
Appleton
$91 Roundtrip, found 2 hours ago
$91
Roundtrip
found 2 hours ago
Select Allegiant Air flight, departing Fri, Dec 4 from Nashville to Appleton, returning Mon, Dec 7, priced at $91 found 2 hours ago
Fri, Dec 4 - Mon, Dec 7
PIE
St. Petersburg
ATW
Appleton
$112 Roundtrip, found 20 hours ago
$112
Roundtrip
found 20 hours ago
Select Allegiant Air flight, departing Fri, Dec 4 from St. Petersburg to Appleton, returning Mon, Dec 7, priced at $112 found 20 hours ago
Thu, Dec 10 - Sun, Dec 13
MCO
Orlando
ATW
Appleton
$118 Roundtrip, found 7 hours ago
$118
Roundtrip
found 7 hours ago
Select Allegiant Air flight, departing Thu, Dec 10 from Orlando to Appleton, returning Sun, Dec 13, priced at $118 found 7 hours ago
Fri, Nov 13 - Mon, Nov 16
FLL
Fort Lauderdale
ATW
Appleton
$124 Roundtrip, found 7 hours ago
$124
Roundtrip
found 7 hours ago
Select Allegiant Air flight, departing Fri, Nov 13 from Fort Lauderdale to Appleton, returning Mon, Nov 16, priced at $124 found 7 hours ago
Mon, Dec 21 - Sat, Jan 2
SFB
Orlando
ATW
Appleton
$136 Roundtrip, found 2 days ago
$136
Roundtrip
found 2 days ago
Select Allegiant Air flight, departing Mon, Dec 21 from Orlando to Appleton, returning Sat, Jan 2, priced at $136 found 2 days ago
Thu, Jan 14 - Sun, Jan 17
PGD
Punta Gorda
ATW
Appleton
$136 Roundtrip, found 3 days ago
$136
Roundtrip
found 3 days ago
Select Allegiant Air flight, departing Thu, Jan 14 from Punta Gorda to Appleton, returning Sun, Jan 17, priced at $136 found 3 days ago
Loading

Deals For This Weekend's Flights

OriginDestinationTravel DatesFlights From*
AZAAppletonNovember 7 to November 17$174
LASAppletonNovember 6 to November 13$275
*Prices include taxes and fees

Find The Perfect Hotel For After Your Flight

Score Epic Sheboygan County Accommodation Deals

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
$132 nightly
The price is $150 total per night from Nov 1 to Nov 2
$150 total
Nov 1 - Nov 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! (1,121 reviews)
"Very outdated. The dishwasher was taped off as broken, broken tiles and grout around the tub, mattresses were terribly hard, pillowcases had makeup on them, the fitness room had three machines and two rusted 5 lb weights, you could not change the channel or adjust volume on tv in the fitness room ..."

Reviewed on Oct 30, 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
$500 nightly
The price is $553 total per night from Nov 1 to Nov 2
$553 total
Nov 1 - Nov 2
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
Blue Harbor Resort and Conference Center

Blue Harbor Resort and Conference Center

3 out of 5
725 Blue Harbor Drive Sheboygan WI
$207 nightly
The price is $235 total per night from Nov 1 to Nov 2
$235 total
Nov 1 - Nov 2
Total with taxes and fees
Book a stay at this beach resort in Sheboygan. Enjoy free WiFi, an outdoor pool, and a full-service spa. Popular attractions Blue Harbor Resort & Conference ...
8.4/10 Very Good! (489 reviews)
"The amenities were closed most of our trip and we were not informed that they would be"

Reviewed on Oct 27, 2026

Opens in a new windowBlue Harbor Resort and Conference Center
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
Watershed Hotel

Watershed Hotel

3 out of 5
838 N 15th St Sheboygan WI
Fully refundableReserve now, pay when you stay
$120 nightly
The price is $137 total per night from Nov 1 to Nov 2
$137 total
Nov 1 - Nov 2
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! (713 reviews)
"Motel was lovely, staff was nice, everything was clean but the mattress was painful, the sheets were scratchy and the pillows were hard. Toilet paper was very soft."

Reviewed on Oct 30, 2026

Opens in a new windowWatershed Hotel
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?

Special

Vehicle determined upon pick-up Compact or Larger
  • 5 people
  • Unlimited mileage
Appleton, Wisconsin, USA
Vehicle determined upon pick-up Compact or Larger

$44

$158 total
found 3 days ago
Special Vehicle determined upon pick-up Compact or Larger

Economy

Mitsubishi Mirage
  • 4 people
  • Unlimited mileage
Appleton, Wisconsin, USA
Mitsubishi Mirage

$50

$180 total
found 3 days ago
Economy Mitsubishi Mirage

Compact

Nissan Versa
  • 5 people
  • Unlimited mileage
Appleton, Wisconsin, USA
Nissan Versa

$51

$182 total
found 3 days ago
Compact Nissan Versa

Midsize

Toyota Corolla
  • 5 people
  • Unlimited mileage
Appleton, Wisconsin, USA
Toyota Corolla

$52

$185 total
found 3 days ago
Midsize Toyota Corolla
Lowest prices found within the past 3 days. Prices and availability subject to change. Additional terms may apply.

Sheboygan County

Get the absolute lowest prices on flights to Sheboygan County by shopping with Orbitz. Orbitz is the most efficient travel planner around, allowing you to search, compare and book discount domestic and international flights fast. With cutting-edge mobile tools and access to frequent flier rewards programs, we have everything you need for both your routine and holiday excursions.

Book Your Flight To Sheboygan County Using Your Mobile Device

New mobile app tools enable those with hand-held devices to scout out the best bargains and to secure tickets from any location. If you have an iPhone, iPad or Android device, you may take advantage of special discounts, only available to mobile device customers, when you book hotel rooms or car rentals on the same day as booking Sheboygan County flights.

Avoid Check-In Hassles When Traveling On Flights to Sheboygan County

Orbitz also provides an array of resources that can help you eliminate most check-in hassles. Detailed baggage information is continually available for Sheboygan County flights. Mobile apps can also be used to share travel itineraries with family members or business associates.

Keeping Everyone Up To Date

When you download the free Orbitz mobile phone app, you can get regular and free flight updates. These will keep you informed of important scheduling changes. Updates can even be sent to several contacts, helping to keep everyone current on anticipated arrival times and all other relevant flight details.

Orbitz makes traveling on a budget very easy to do. We provide everything you need to plan your ideal trip from start to finish. Getting there and back again is a snap when you book your Sheboygan County flight using Orbitz.

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 $91 this past week to Sheboygan County, and peaked at $275. Several lucky travelers journeying out of Orlando (MCO) managed to land one-way tickets from just $56.
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.