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Hilton Head Island

$184+ 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 9/29. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — HHH
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
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 June 12, 2025.

Round-trip from

$234
(American Airlines)

One-way from

$189
(American Airlines)

Popular in

March

Cheapest in

November

Average price

$543
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 ($247 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 June 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 June 12, 2025.

This American Airlines deal was found by Cheapflights users on 6/10. 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 8/136:32 amMKE - HHH
1 stop5h 12mAmerican Airlines
Mon 8/185:28 pmHHH - MKE
1 stop6h 36mAmerican Airlines
Deal found 6/10$234
This Delta deal was found by Cheapflights users on 6/9. 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 6/309:49 amORD - HHH
1 stop4h 29mDelta
Wed 7/163:58 pmHHH - ORD
1 stop7h 29mDelta
Deal found 6/9$249
This American Airlines deal was found by Cheapflights users on 6/11. 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 9/2010:58 amMSP - HHH
1 stop4h 49mAmerican Airlines
Sat 9/275:19 pmHHH - MSP
1 stop5h 16mAmerican Airlines
Deal found 6/11$259
This Delta deal was found by Cheapflights users on 6/9. 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 6/307:05 amMKE - HHH
1 stop7h 13mDelta
Fri 7/113:58 pmHHH - MKE
1 stop6h 17mDelta
Deal found 6/9$274
This American Airlines deal was found by Cheapflights users on 6/10. 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 10/17:48 amMSN - HHH
1 stop6h 08mAmerican Airlines
Wed 10/812:46 pmHHH - MSN
2 stops9h 52mAmerican Airlines
Deal found 6/10$289
This American Airlines deal was found by Cheapflights users on 6/11. 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 9/2710:00 amORD - HHH
Nonstop2h 27mAmerican Airlines
Sat 10/411:28 amHHH - ORD
1 stop5h 22mAmerican Airlines
Deal found 6/11$299
This Delta deal was found by Cheapflights users on 6/10. 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 7/155:03 pmGRB - HHH
2 stops17h 20mDelta
Tue 7/223:58 pmHHH - GRB
2 stops20h 32mDelta
Deal found 6/10$428
This American Airlines deal was found by Cheapflights users on 6/10. 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 9/176:29 amATW - HHH
2 stops9h 18mAmerican Airlines
Wed 9/243:26 pmHHH - ATW
2 stops7h 59mAmerican Airlines
Deal found 6/10$429
This American Airlines deal was found by Cheapflights users on 6/11. 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 7/156:15 amGRB - HHH
2 stops7h 00mAmerican Airlines
Tue 7/225:49 pmHHH - GRB
2 stops6h 40mAmerican Airlines
Deal found 6/11$432
This Delta deal was found by Cheapflights users on 6/10. 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 7/166:25 amATW - HHH
2 stops7h 53mDelta
Tue 7/2212:05 pmHHH - ATW
2 stops9h 36mDelta
Deal found 6/10$464
This United Airlines deal was found by Cheapflights users on 6/11. 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 7/510:35 amORD - HHH
Nonstop2h 26mUnited Airlines
Sat 7/125:00 pmHHH - ORD
Nonstop2h 35mUnited Airlines
Deal found 6/11$468
This Delta deal was found by Cheapflights users on 6/10. 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.
Fri 7/257:15 amMSP - HHH
1 stop7h 03mDelta
Mon 7/2812:05 pmHHH - MSP
1 stop6h 20mDelta
Deal found 6/10$588

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 June 12, 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

Wed 8/13

6:32 am-12:44 pm

1 stop5h 12m

Hilton Head Island

Mon 8/18

5:28 pm-11:04 pm

1 stop6h 36m

$234

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Mon 6/30

9:49 am-3:18 pm

1 stop4h 29m

Hilton Head Island

Wed 7/16

3:58 pm-10:27 pm

1 stop7h 29m

$249

MinneapolisHilton Head Island

MSP - HHH

MSPHHH

Minneapolis St Paul

Sat 9/20

10:58 am-4:47 pm

1 stop4h 49m

Hilton Head Island

Sat 9/27

5:19 pm-9:35 pm

1 stop5h 16m

$259

MilwaukeeHilton Head Island

MKE - HHH

MKEHHH

Milwaukee-Mitchell

Mon 6/30

7:05 am-3:18 pm

1 stop7h 13m

Hilton Head Island

Fri 7/11

3:58 pm-9:15 pm

1 stop6h 17m

$274

MadisonHilton Head Island

MSN - HHH

MSNHHH

Madison Truax Field

Wed 10/1

7:48 am-2:56 pm

1 stop6h 08m

Hilton Head Island

Wed 10/8

12:46 pm-9:38 pm

2 stops9h 52m

$289

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Sat 9/27

10:00 am-1:27 pm

Nonstop2h 27m

Hilton Head Island

Sat 10/4

11:28 am-3:50 pm

1 stop5h 22m

$299

Green BayHilton Head Island

GRB - HHH

GRBHHH

Green Bay Austin-Straubel

Tue 7/15

5:03 pm-11:23 am

2 stops17h 20m

Hilton Head Island

Tue 7/22

3:58 pm-11:30 am

2 stops20h 32m

$428

Green BayHilton Head Island

GRB - HHH

GRBHHH

Green Bay Austin-Straubel

Tue 7/15

6:15 am-2:15 pm

2 stops7h 00m

Hilton Head Island

Tue 7/22

5:49 pm-11:29 pm

2 stops6h 40m

$432

AppletonHilton Head Island

ATW - HHH

ATWHHH

Appleton Intl

Wed 7/16

6:25 am-3:18 pm

2 stops7h 53m

Hilton Head Island

Tue 7/22

12:05 pm-8:41 pm

2 stops9h 36m

$464

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Sat 7/5

10:35 am-2:01 pm

Nonstop2h 26m

Hilton Head Island

Sat 7/12

5:00 pm-6:35 pm

Nonstop2h 35m

$468

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/10

Showing 1-10 of 22 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 June 12, 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 June 12, 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
7,946 reviews

Entertainment

7.9

Overall

8.0

Boarding

8.2

Food

7.3

Crew

8.5

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Delta
8.0
Very good
7,946 reviews
Delta
8.0
Very good
7,946 reviews

Entertainment

7.9

Overall

8.0

Boarding

8.2

Food

7.3

Crew

8.5

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
United Airlines
7.4
Good
8,790 reviews
Delta
8.0
Very good
7,946 reviews

Entertainment

7.9

Overall

8.0

Boarding

8.2

Food

7.3

Crew

8.5

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,946 reviews

Entertainment

7.9

Overall

8.0

Boarding

8.2

Food

7.3

Crew

8.5

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

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 American Airlines, which is currently one of the cheapest options available, starting at $189. Delta flights start at $218 while deals on United Airlines start at $259 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 Green Bay Austin-Straubel - 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 June 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$221Average$495FlexibilityNo cancel feeOn-time71%
DeltaCheapest$223Average$419FlexibilityNo cancel feeOn-timeN/A

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