$53 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 church with two spires, surrounded by autumn foliage.
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Kohler

Kohler

Cheap flights to Sheboygan County from $53 One Way, $96 Round Trip

$96 return flights and $53 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 25 - Mon, Sep 28
BNA
Nashville
ATW
Appleton
$96 Roundtrip, found 4 days ago
$96
Roundtrip
found 4 days ago
Select Allegiant Air flight, departing Fri, Sep 25 from Nashville to Appleton, returning Mon, Sep 28, priced at $96 found 4 days ago
Thu, Dec 3 - Sun, Dec 13
MCO
Orlando
ATW
Appleton
$112 Roundtrip, found 6 days ago
$112
Roundtrip
found 6 days ago
Select Allegiant Air flight, departing Thu, Dec 3 from Orlando to Appleton, returning Sun, Dec 13, priced at $112 found 6 days ago
Mon, Sep 21 - Mon, Sep 28
RSW
Fort Myers
ATW
Appleton
$122 Roundtrip, found 4 days ago
$122
Roundtrip
found 4 days ago
Select Allegiant Air flight, departing Mon, Sep 21 from Fort Myers to Appleton, returning Mon, Sep 28, priced at $122 found 4 days ago
Fri, Oct 2 - Mon, Oct 5
FLL
Fort Lauderdale
ATW
Appleton
$124 Roundtrip, found 1 day ago
$124
Roundtrip
found 1 day ago
Select Allegiant Air flight, departing Fri, Oct 2 from Fort Lauderdale to Appleton, returning Mon, Oct 5, priced at $124 found 1 day ago
Thu, Jan 21 - Mon, Jan 25
PGD
Punta Gorda
ATW
Appleton
$128 Roundtrip, found 23 hours ago
$128
Roundtrip
found 23 hours ago
Select Allegiant Air flight, departing Thu, Jan 21 from Punta Gorda to Appleton, returning Mon, Jan 25, priced at $128 found 23 hours ago
Sat, Jan 9 - Mon, Jan 11
SFB
Orlando
ATW
Appleton
$130 Roundtrip, found 6 days ago
$130
Roundtrip
found 6 days ago
Select Allegiant Air flight, departing Sat, Jan 9 from Orlando to Appleton, returning Mon, Jan 11, priced at $130 found 6 days ago

Deals For This Weekend's Flights

OriginDestinationTravel DatesFlights From*
DENAppletonSeptember 11 to September 18$237
SANAppletonSeptember 12 to September 15$432
DTWAppletonSeptember 11 to September 14$475
*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
$132 nightly
The price is $150 total per night from Sep 27 to Sep 28
$150 total
Sep 27 - Sep 28
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! (1,083 reviews)
"Smaller pool and exercise room, but offers them versus other hotels that don't. Overall, great location as it was close to everything, pharmacy, food, etc."

Reviewed on Sep 7, 2026

Opens in a new windowGrandstay Residential Suites Hotel - Sheboygan
Watershed Hotel

Watershed Hotel

3 out of 5
838 N 15th St Sheboygan WI
Fully refundableReserve now, pay when you stay
$119 nightly
The price is $135 total per night from Oct 9 to Oct 10
$135 total
Oct 9 - Oct 10
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! (647 reviews)
"This was an absolutely wonderful place. The staff was excellent and very helpful. We were able to walk to other places safely, although most of the restaurants were 3/4 of a mile away or more. I would absolutely recommend this hotel!"

Reviewed on Sep 7, 2026

Opens in a new windowWatershed Hotel
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
$88 nightly
The price is $100 total per night from Oct 4 to Oct 5
$100 total
Oct 4 - Oct 5
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 ...
Opens in a new windowAmericInn by Wyndham Sheboygan
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The American Club

The American Club

5 out of 5
419 Highland Drive Kohler WI
Fully refundable
$645 nightly
The price is $713 total per night from Sep 20 to Sep 21
$713 total
Sep 20 - Sep 21
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 ...
9.6/10 Exceptional! (267 reviews)
"The room was dark and very outdated. It smelled very musty and damp. There were no overhead lights other than above the bed. Dark and depressing. Not in anyway worth $900. The building itself is beautiful but a very dreary experience. Overpriced"

Reviewed on Aug 23, 2026

Opens in a new windowThe American Club
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

Orbitz is your one stop for guaranteed low prices on Sheboygan County flights, as well as budget deals on hotels and rental cars. Use our state of the art mobile tools to get great deals and constant updates on the status of your trip.

Save Big On Car Rentals Too

Orbitz will find you discount air fare for flights to Sheboygan County and you can rent a car at the same time. With Orbitzyou will get a discount on the rental and have your car waiting for you when you land.

Get Free Travel Advice By Calling the Orbitz Hotline

Our experts will make things even easier by helping you to find the best budget flights to Sheboygan County Just call our toll free hotline at 1-800-649-9920 and one of our travel advisors will be happy to assist you with everything from your flight to hotel room.

Book Travel on the Fly with Orbitz on the Go

Our state of the art mobile apps will allow you to book cheap flights to Sheboygan County from your smartphone too. Discount airfare is not all; you can also find mobile-only hotel deals or check the status of your flight using this free app. So, when you’re on the go, why not take Orbitz with you?

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 $96 this past week to Sheboygan County, and peaked at $475. Several lucky travelers journeying out of Orlando (MCO) managed to land one-way tickets from just $53.
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.