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Hilton Head Island

$164+ Cheap flights from Wisconsin to Hilton Head Island (HHH)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 2/7. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — HHH
Feb 7 — Feb 141
Sat 2/7
Sat 2/14
1 adult, Economy
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Cheap flight deals from Wisconsin to Hilton Head Island

Keep the following information in mind while searching for Wisconsin to Hilton Head Island flight deals. Data was last updated January 8, 2026.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$249
(Delta)

One-way from

$164
(American Airlines)

Popular in

March

Cheapest in

January

Average price

$238
Provider with most accurate pricing for Milwaukee-Mitchell-Hilton Head Island flight deals.
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Provider most trusted by Cheapflights users for Milwaukee-Mitchell-Hilton Head Island flights.
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From Wisconsin to Hilton Head Island
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One-way flight from Wisconsin to Hilton Head Island
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Highest demand for flights based on searches. 25% potential increase in price ($152 potential increase over avg. RT price).
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Cheapest flight prices on average. 11% potential price decrease ($44 potential savings vs. average RT price).
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Average for round-trip flights in January 2026
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Find flight deals from Wisconsin to Hilton Head Island

Cheapest flights from Wisconsin to Hilton Head Island
Explore the most affordable flight options available from Wisconsin to Hilton Head Island. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 8, 2026.

This United Airlines deal was found by Cheapflights users on 1/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/1910:35 amORD - HHH
Nonstop2h 26mUnited Airlines
Sat 9/263:00 pmHHH - ORD
Nonstop2h 45mUnited Airlines
Deal found 1/7$220
This Delta deal was found by Cheapflights users on 1/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/287:10 amORD - HHH
1 stop7h 10mDelta
Tue 8/44:00 pmHHH - ORD
1 stop7h 43mDelta
Deal found 1/6$229
This Delta deal was found by Cheapflights users on 1/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/297:10 amORD - HHH
1 stop7h 10mDelta
Tue 8/44:00 pmHHH - ORD
1 stop7h 43mDelta
Deal found 1/6$269
This United Airlines deal was found by Cheapflights users on 1/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/66:30 amMSP - HHH
1 stop6h 31mUnited Airlines
Tue 8/113:00 pmHHH - MSP
1 stop7h 01mUnited Airlines
Deal found 1/8$279
This United Airlines deal was found by Cheapflights users on 1/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/2710:35 amORD - HHH
Nonstop2h 26mUnited Airlines
Wed 8/53:00 pmHHH - ORD
Nonstop2h 45mUnited Airlines
Deal found 1/6$279
This Delta deal was found by Cheapflights users on 1/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/217:00 amMKE - HHH
1 stop7h 10mDelta
Tue 4/283:50 pmHHH - MKE
1 stop6h 45mDelta
Deal found 1/7$283
This American Airlines deal was found by Cheapflights users on 1/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/1910:07 amORD - HHH
Nonstop2h 24mAmerican Airlines
Sat 9/264:03 pmHHH - ORD
1 stop6h 18mAmerican Airlines
Deal found 1/7$299
This American Airlines deal was found by Cheapflights users on 1/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/158:35 amORD - HHH
1 stop4h 37mAmerican Airlines
Sat 8/226:15 pmHHH - ORD
1 stop6h 33mAmerican Airlines
Deal found 1/7$309
This American Airlines deal was found by Cheapflights users on 1/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/146:00 amATW - HHH
1 stop7h 22mAmerican Airlines
Sat 2/216:20 pmHHH - ATW
1 stop6h 25mAmerican Airlines
Deal found 1/5$319
This American Airlines deal was found by Cheapflights users on 1/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/57:20 amMSP - HHH
1 stop6h 39mAmerican Airlines
Thu 2/126:20 pmHHH - MSP
1 stop5h 59mAmerican Airlines
Deal found 1/6$319
This Delta deal was found by Cheapflights users on 1/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/279:30 amORD - HHH
1 stop4h 50mDelta
Tue 8/44:00 pmHHH - ORD
1 stop7h 43mDelta
Deal found 1/6$334
This American Airlines deal was found by Cheapflights users on 1/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/212:00 pmMKE - HHH
1 stop5h 20mAmerican Airlines
Sat 5/94:10 pmHHH - MKE
1 stop7h 24mAmerican Airlines
Deal found 1/8$336

Cheapflights Fare Finder

 
Customize your flight search to find flights from Wisconsin to Hilton Head Island that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated January 8, 2026.
Use the filters below to find and compare flights from Wisconsin to Hilton Head Island that are best for you.

Fly from

Wisconsin

Fly to

Hilton Head Island

Route

Depart

Return

Price

MilwaukeeHilton Head Island

MKE - HHH

MKEHHH

Milwaukee-Mitchell

Tue 4/21

7:00 am-3:10 pm

1 stop7h 10m

Hilton Head Island

Tue 4/28

3:50 pm-9:35 pm

1 stop6h 45m

$283

MinneapolisHilton Head Island

MSP - HHH

MSPHHH

Minneapolis St Paul

Wed 3/4

7:03 am-3:41 pm

1 stop7h 38m

Hilton Head Island

Mon 3/9

4:11 pm-9:56 pm

1 stop6h 45m

$319

MinneapolisHilton Head Island

MSP - HHH

MSPHHH

Minneapolis St Paul

Thu 3/5

7:03 am-3:41 pm

1 stop7h 38m

Hilton Head Island

Mon 3/9

4:11 pm-9:56 pm

1 stop6h 45m

$319

MinneapolisHilton Head Island

MSP - HHH

MSPHHH

Minneapolis St Paul

Sat 2/14

6:15 am-2:22 pm

1 stop7h 07m

Hilton Head Island

Sat 2/21

6:20 pm-11:23 pm

1 stop6h 03m

$319

MinneapolisHilton Head Island

MSP - HHH

MSPHHH

Minneapolis St Paul

Thu 2/5

7:20 am-2:59 pm

1 stop6h 39m

Hilton Head Island

Thu 2/12

6:20 pm-11:19 pm

1 stop5h 59m

$319

AppletonHilton Head Island

ATW - HHH

ATWHHH

Appleton Intl

Sat 2/14

6:00 am-2:22 pm

1 stop7h 22m

Hilton Head Island

Sat 2/21

6:20 pm-11:45 pm

1 stop6h 25m

$319

MilwaukeeHilton Head Island

MKE - HHH

MKEHHH

Milwaukee-Mitchell

Sat 5/2

12:00 pm-6:20 pm

1 stop5h 20m

Hilton Head Island

Sat 5/9

4:10 pm-10:34 pm

1 stop7h 24m

$336

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Fri 3/13

7:12 am-2:22 pm

1 stop6h 10m

Hilton Head Island

Sat 3/21

4:31 pm-9:15 pm

1 stop5h 44m

$336

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Mon 3/16

8:10 am-2:22 pm

1 stop5h 12m

Hilton Head Island

Sat 3/21

4:31 pm-9:15 pm

1 stop5h 44m

$336

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Sat 1/31

8:50 pm-12:20 pm

2 stops14h 30m

Hilton Head Island

Mon 2/2

12:51 pm-6:01 pm

1 stop6h 10m

$337

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/7

Showing 1-10 of 50 results
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Best time to book a flight from Wisconsin to Hilton Head Island

Have a flexible travel schedule? Discover the best time to fly to Hilton Head Island from Wisconsin with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Wisconsin to Hilton Head Island

What is the cheapest month to book a flight from Wisconsin to Hilton Head Island?

Currently, February is the cheapest month in which you can book a flight from Wisconsin to Hilton Head Island (average of $84). Flying from Wisconsin to Hilton Head Island in November is currently the most expensive (average of $248). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

Related info for your journey

Find useful and relevant information for your journey from Wisconsin to Hilton Head Island. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to Hilton Head Island from Wisconsin?

    For a flight from Wisconsin to Hilton Head Island, you will be flying into Hilton Head. Hilton Head Island (HHH) is just 3.3 mi from the center of the city.

  • How long is the flight from Wisconsin to Hilton Head Island?

    Airlines like Delta, American Airlines, and United Airlines fly from Wisconsin to Hilton Head Island in about 6h 26m. The time it takes to get you to your destination can typically vary by up to 1h 12m. Airlines will cover a distance of 932 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the most popular routes from Wisconsin to Hilton Head Island?

    While some choose either Minneapolis St Paul - Hilton Head Island or Madison Truax Field - Hilton Head Island, Chicago O'Hare Intl - Hilton Head Island is the most popular route from Wisconsin to Hilton Head Island.

  • Can I find deals for flights from Wisconsin to Hilton Head Island that include hotel bookings?

    Yes. In addition to deals on Wisconsin to Hilton Head Island flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Wisconsin to Hilton Head Island?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Wisconsin to Hilton Head Island.

  • Can I find deals for business class flights from Wisconsin to Hilton Head Island?

    Yes. Cheapflights offers flight deals from Wisconsin to Hilton Head Island by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Wisconsin to Hilton Head Island?

    Currently, February is the cheapest month in which you can book a flight from Wisconsin to Hilton Head Island (average of $84). Flying from Wisconsin to Hilton Head Island in November is currently the most expensive (average of $248). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Hilton Head Island?

Book flights to Hilton Head Island if you plan to visit one of these locations
Beaufort

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Alternative routes for Wisconsin to Hilton Head Island

See prices for flight routes from nearby airports that may be better suited for you.
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Top 2 airlines flying from Wisconsin to Hilton Head Island

Discover the top 2 airlines that operate flights from Wisconsin to Hilton Head Island. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated January 8, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$223Average$383FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$233Average$468FlexibilityNo cancel feeOn-time71%

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