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Hilton Head Island

$199+ 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 10/25. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — HHH
Oct 17 — Oct 241
Fri 10/17
Fri 10/24
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 September 17, 2025.

Round-trip from

$249
(American Airlines)

One-way from

$199
(American Airlines)

Popular in

March

Cheapest in

November

Average price

$313
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. 34% potential increase in price ($254 potential increase over avg. RT price).
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Cheapest flight prices on average. 18% potential price decrease ($76 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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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 September 17, 2025.

This American Airlines deal was found by Cheapflights users on 9/14. 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 11/86:14 amMKE - HHH
1 stop7h 05mAmerican Airlines
Wed 11/127:07 pmHHH - MKE
1 stop4h 49mAmerican Airlines
Deal found 9/14$249
This American Airlines deal was found by Cheapflights users on 9/15. 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.
Tue 9/307:30 amMSN - HHH
1 stop6h 26mAmerican Airlines
Sat 10/45:19 pmHHH - MSN
1 stop6h 51mAmerican Airlines
Deal found 9/15$259
This American Airlines deal was found by Cheapflights users on 9/15. 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 11/156:18 amMSP - HHH
1 stop7h 01mAmerican Airlines
Sat 11/226:40 pmHHH - MSP
1 stop5h 53mAmerican Airlines
Deal found 9/15$259
This American Airlines deal was found by Cheapflights users on 9/15. 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.
Tue 12/26:29 amMKE - HHH
1 stop5h 01mAmerican Airlines
Sat 12/66:48 pmHHH - MKE
1 stop6h 13mAmerican Airlines
Deal found 9/15$274
This American Airlines deal was found by Cheapflights users on 9/16. 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.
Fri 11/1411:06 amMSP - HHH
1 stop6h 31mAmerican Airlines
Fri 12/53:27 pmHHH - MSP
2 stops9h 32mAmerican Airlines
Deal found 9/16$279
This American Airlines deal was found by Cheapflights users on 9/16. 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 10/2510:05 amORD - HHH
Nonstop2h 20mAmerican Airlines
Tue 10/283:32 pmHHH - ORD
1 stop4h 38mAmerican Airlines
Deal found 9/16$299
This American Airlines deal was found by Cheapflights users on 9/17. 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.
Wed 11/1212:20 pmMSN - HHH
1 stop5h 17mAmerican Airlines
Mon 11/177:07 pmHHH - MSN
1 stop5h 23mAmerican Airlines
Deal found 9/17$319
This American Airlines deal was found by Cheapflights users on 9/17. 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.
Fri 11/1411:06 amMSP - HHH
1 stop6h 31mAmerican Airlines
Sun 11/236:40 pmHHH - MSP
1 stop5h 28mAmerican Airlines
Deal found 9/17$319
This American Airlines deal was found by Cheapflights users on 9/15. 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 11/86:50 amORD - HHH
2 stops6h 29mAmerican Airlines
Tue 11/111:02 pmHHH - ORD
2 stops7h 39mAmerican Airlines
Deal found 9/15$319
This Delta deal was found by Cheapflights users on 9/15. 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 9/169:50 amORD - HHH
1 stop4h 35mDelta
Tue 9/2312:14 pmHHH - ORD
1 stop5h 17mDelta
Deal found 9/15$324
This Delta deal was found by Cheapflights users on 9/14. 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.
Thu 9/257:20 amORD - HHH
1 stop7h 05mDelta
Mon 9/294:05 pmHHH - ORD
1 stop5h 30mDelta
Deal found 9/14$327
This American Airlines deal was found by Cheapflights users on 9/15. 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.
Mon 11/176:58 amATW - HHH
1 stop4h 31mAmerican Airlines
Sun 11/236:40 pmHHH - ATW
1 stop5h 08mAmerican Airlines
Deal found 9/15$329

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 September 17, 2025.
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

Sat 11/8

6:14 am-2:19 pm

1 stop7h 05m

Hilton Head Island

Wed 11/12

7:07 pm-10:56 pm

1 stop4h 49m

$249

MilwaukeeHilton Head Island

MKE - HHH

MKEHHH

Milwaukee-Mitchell

Tue 2/3

7:17 am-2:18 pm

1 stop6h 01m

Hilton Head Island

Mon 2/9

6:14 pm-9:25 pm

1 stop4h 11m

$249

MadisonHilton Head Island

MSN - HHH

MSNHHH

Madison Truax Field

Tue 9/30

7:30 am-2:56 pm

1 stop6h 26m

Hilton Head Island

Sat 10/4

5:19 pm-11:10 pm

1 stop6h 51m

$259

MinneapolisHilton Head Island

MSP - HHH

MSPHHH

Minneapolis St Paul

Sun 1/11

10:24 am-5:34 pm

1 stop6h 10m

Hilton Head Island

Sat 1/31

6:14 pm-12:13 am

1 stop6h 59m

$259

MinneapolisHilton Head Island

MSP - HHH

MSPHHH

Minneapolis St Paul

Fri 11/14

11:06 am-6:37 pm

1 stop6h 31m

Hilton Head Island

Fri 12/5

3:27 pm-9:47 pm

1 stop7h 20m

$259

MilwaukeeHilton Head Island

MKE - HHH

MKEHHH

Milwaukee-Mitchell

Tue 12/2

6:29 am-12:30 pm

1 stop5h 01m

Hilton Head Island

Sat 12/6

6:48 pm-12:01 am

1 stop6h 13m

$274

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Sat 10/25

10:05 am-1:25 pm

Nonstop2h 20m

Hilton Head Island

Tue 10/28

3:32 pm-7:10 pm

1 stop4h 38m

$299

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Tue 2/3

6:00 am-2:18 pm

2 stops7h 18m

Hilton Head Island

Tue 2/10

4:00 pm-7:26 pm

1 stop4h 26m

$314

MadisonHilton Head Island

MSN - HHH

MSNHHH

Madison Truax Field

Wed 11/12

12:20 pm-6:37 pm

1 stop5h 17m

Hilton Head Island

Mon 11/17

7:07 pm-11:30 pm

1 stop5h 23m

$319

MinneapolisHilton Head Island

MSP - HHH

MSPHHH

Minneapolis St Paul

Fri 11/14

11:06 am-6:37 pm

1 stop6h 31m

Hilton Head Island

Sun 11/23

6:40 pm-11:08 pm

1 stop5h 28m

$319

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/17

Showing 1-10 of 51 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, January is the cheapest month in which you can book a flight from Wisconsin to Hilton Head Island (average of $275). Flying from Wisconsin to Hilton Head Island in March is currently the most expensive (average of $479). 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.

What is the cheapest time of day to fly from WI to HHH?

Find hourly flight availability from Wisconsin to Hilton Head Island. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 17, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Wisconsin to Hilton Head Island as you normally would.

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 American Airlines fly from Wisconsin to Hilton Head Island in about 7h 05m. The time it takes to get you to your destination can typically vary by up to . Airlines will cover a distance of 838 mi.

  • What are the cheapest airlines to fly from Wisconsin to Hilton Head Island one-way?

    To fly one-way, consider booking your trip with American Airlines, which is currently one of the cheapest options available, starting at $199. Delta flights start at $214 while deals on United Airlines start at $395 one-way.

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

    While some choose either Minneapolis St Paul - Hilton Head Island or Milwaukee-Mitchell - 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, January is the cheapest month in which you can book a flight from Wisconsin to Hilton Head Island (average of $275). Flying from Wisconsin to Hilton Head Island in March is currently the most expensive (average of $479). 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
Bluffton

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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 September 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$248Average$480FlexibilityNo cancel feeOn-time71%
DeltaCheapest$323Average$383FlexibilityNo cancel feeOn-timeN/A

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