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Hilton Head Island

$166+ 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 6/3. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — HHH
May 6 — May 131
Tue 5/6
Tue 5/13
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 May 1, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$229
(Delta)

One-way from

$166
(Delta)

Popular in

March

Cheapest in

November

Average price

$406
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. 34% potential increase in price ($246 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 May 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 May 1, 2025.

This Delta deal was found by Cheapflights users on 4/29. 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 6/109:49 amORD - HHH
1 stop4h 29mDelta
Tue 6/173:58 pmHHH - ORD
1 stop7h 23mDelta
Deal found 4/29$229
This Delta deal was found by Cheapflights users on 4/29. 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 7/157:00 amMKE - HHH
1 stop7h 15mDelta
Tue 7/2212:03 pmHHH - MKE
1 stop5h 57mDelta
Deal found 4/29$249
This American Airlines deal was found by Cheapflights users on 4/30. 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 9/246:28 amMSN - HHH
2 stops10h 05mAmerican Airlines
Sat 9/276:22 pmHHH - MSN
1 stop4h 06mAmerican Airlines
Deal found 4/30$254
This American Airlines deal was found by Cheapflights users on 4/29. 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 7/225:06 amMKE - HHH
2 stops8h 09mAmerican Airlines
Tue 7/295:49 pmHHH - MKE
2 stops6h 14mAmerican Airlines
Deal found 4/29$259
This American Airlines deal was found by Cheapflights users on 4/29. 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 5/299:54 amMSP - HHH
1 stop6h 56mAmerican Airlines
Thu 6/55:50 pmHHH - MSP
1 stop7h 09mAmerican Airlines
Deal found 4/29$269
This American Airlines deal was found by Cheapflights users on 4/30. 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 7/199:17 amORD - HHH
1 stop7h 22mAmerican Airlines
Sat 7/2611:01 amHHH - ORD
1 stop5h 51mAmerican Airlines
Deal found 4/30$309
This United Airlines deal was found by Cheapflights users on 4/29. 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 7/1910:35 amORD - HHH
Nonstop2h 26mUnited Airlines
Sat 7/265:00 pmHHH - ORD
Nonstop2h 35mUnited Airlines
Deal found 4/29$369
This United Airlines deal was found by Cheapflights users on 4/29. 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.
Fri 5/95:30 pmGRB - HHH
2 stops21h 34mUnited Airlines
Tue 5/134:10 pmHHH - GRB
2 stops19h 05mUnited Airlines
Deal found 4/29$588
This United Airlines deal was found by Cheapflights users on 4/29. 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 5/299:05 amMSP - HHH
2 stops24h 59mUnited Airlines
Thu 6/511:17 amHHH - MSP
3 stops29h 37mUnited Airlines
Deal found 4/29$616
This United Airlines deal was found by Cheapflights users on 4/30. 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 5/176:30 amMSN - HHH
1 stop6h 29mUnited Airlines
Sat 5/245:00 pmHHH - MSN
1 stop20h 13mUnited Airlines
Deal found 4/30$652

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 May 1, 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

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Tue 6/10

9:49 am-3:18 pm

1 stop4h 29m

Hilton Head Island

Tue 6/17

3:58 pm-10:21 pm

1 stop7h 23m

$229

MilwaukeeHilton Head Island

MKE - HHH

MKEHHH

Milwaukee-Mitchell

Tue 7/15

7:00 am-3:15 pm

1 stop7h 15m

Hilton Head Island

Tue 7/22

12:03 pm-5:00 pm

1 stop5h 57m

$249

MadisonHilton Head Island

MSN - HHH

MSNHHH

Madison Truax Field

Wed 9/24

6:28 am-5:33 pm

2 stops10h 05m

Hilton Head Island

Sat 9/27

6:22 pm-9:28 pm

1 stop4h 06m

$254

MilwaukeeHilton Head Island

MKE - HHH

MKEHHH

Milwaukee-Mitchell

Tue 7/22

5:06 am-2:15 pm

2 stops8h 09m

Hilton Head Island

Tue 7/29

5:49 pm-11:03 pm

2 stops6h 14m

$259

MinneapolisHilton Head Island

MSP - HHH

MSPHHH

Minneapolis St Paul

Thu 5/29

9:54 am-5:50 pm

1 stop6h 56m

Hilton Head Island

Thu 6/5

5:50 pm-11:59 pm

1 stop7h 09m

$269

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Sat 7/19

9:17 am-5:39 pm

1 stop7h 22m

Hilton Head Island

Sat 7/26

11:01 am-3:52 pm

1 stop5h 51m

$309

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Sat 7/19

10:35 am-2:01 pm

Nonstop2h 26m

Hilton Head Island

Sat 7/26

5:00 pm-6:35 pm

Nonstop2h 35m

$369

MinneapolisHilton Head Island

MSP - HHH

MSPHHH

Minneapolis St Paul

Thu 5/29

9:05 am-11:04 am

2 stops24h 59m

Hilton Head Island

Thu 6/5

11:17 am-3:54 pm

3 stops29h 37m

$616

MadisonHilton Head Island

MSN - HHH

MSNHHH

Madison Truax Field

Sat 5/17

6:30 am-1:59 pm

1 stop6h 29m

Hilton Head Island

Sat 5/24

5:00 pm-12:13 pm

1 stop20h 13m

$652

MilwaukeeHilton Head Island

MKE - HHH

MKEHHH

Milwaukee-Mitchell

Tue 6/3

10:23 am-3:20 pm

1 stop3h 57m

$166

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/29

Showing 1-10 of 17 results
1
2

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 May 1, 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.

Rainfall in Hilton Head Island by month

Plan your trip to Hilton Head Island by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Hilton Head Island ranges from 2.4 - 7.8 inches per month. August is typically the wettest month, when rainfall can reach 7.8 in. November is typically the driest time to visit Hilton Head Island when rainfall is around 2.4 in.

Temperature in Hilton Head Island by month

Plan your trip to Hilton Head Island by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Hilton Head Island, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 80.6 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 50.0 F).

Reviews of airlines servicing Hilton Head Island

Get insights into the airlines that provide service to Hilton Head Island. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Hilton Head Island. Reviews last updated May 1, 2025.
Read through reviews of airlines operating flights from Wisconsin to Hilton Head Island, such as Delta, United Airlines and American Airlines. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,934 reviews

Overall

8.0

Comfort

7.9

Boarding

8.2

Food

7.3

Crew

8.5

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
Delta
8.0
Very good
7,934 reviews
Delta
8.0
Very good
7,934 reviews

Overall

8.0

Comfort

7.9

Boarding

8.2

Food

7.3

Crew

8.5

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
United Airlines
7.4
Good
8,696 reviews
Delta
8.0
Very good
7,934 reviews

Overall

8.0

Comfort

7.9

Boarding

8.2

Food

7.3

Crew

8.5

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,934 reviews

Overall

8.0

Comfort

7.9

Boarding

8.2

Food

7.3

Crew

8.5

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

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.

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

    To fly one-way, consider booking your trip with Delta, which is currently one of the cheapest options available, starting at $166. American Airlines flights start at $189 while deals on United Airlines start at $214 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 Wisconsin?

Book flights to Wisconsin if you plan to visit one of these locations
Beaufort
Bluffton

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Alternative routes for Wisconsin to Hilton Head Island

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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 May 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$221Average$500FlexibilityNo cancel feeOn-time71%
DeltaCheapest$223Average$506FlexibilityNo cancel feeOn-timeN/A

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