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Hilton Head Island

$150+ 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 11/24. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — HHH
Dec 13 — Dec 201
Sat 12/13
Sat 12/20
1 adult, Economy
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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 November 13, 2025.

This American Airlines deal was found by Cheapflights users on 11/12. 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 11/275:00 amORD - HHH
1 stop4h 24mAmerican Airlines
Mon 12/16:40 pmHHH - ORD
1 stop6h 00mAmerican Airlines
Deal found 11/12$367
This American Airlines deal was found by Cheapflights users on 11/12. 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 11/188:00 amMSN - HHH
1 stop5h 57mAmerican Airlines
Sat 11/226:40 pmHHH - MSN
1 stop6h 11mAmerican Airlines
Deal found 11/12$389
This American Airlines deal was found by Cheapflights users on 11/12. 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 11/156:14 amMKE - HHH
1 stop4h 02mAmerican Airlines
Wed 11/191:02 pmHHH - MKE
1 stop4h 55mAmerican Airlines
Deal found 11/12$389
This American Airlines deal was found by Cheapflights users on 11/11. 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.
Mon 12/225:00 amORD - HHH
1 stop4h 44mAmerican Airlines
Mon 12/2911:14 amHHH - ORD
1 stop5h 51mAmerican Airlines
Deal found 11/11$394
This American Airlines deal was found by Cheapflights users on 11/11. 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.
Wed 11/198:20 amORD - HHH
1 stop5h 37mAmerican Airlines
Sun 11/2311:28 amHHH - ORD
1 stop6h 25mAmerican Airlines
Deal found 11/11$397
This American Airlines deal was found by Cheapflights users on 11/11. 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.
Thu 12/48:20 amORD - HHH
1 stop4h 27mAmerican Airlines
Sun 12/76:52 pmHHH - ORD
1 stop5h 54mAmerican Airlines
Deal found 11/11$425
This American Airlines deal was found by Cheapflights users on 11/12. 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 12/235:00 amORD - HHH
1 stop4h 44mAmerican Airlines
Mon 12/2911:14 amHHH - ORD
1 stop5h 51mAmerican Airlines
Deal found 11/12$427
This American Airlines deal was found by Cheapflights users on 11/11. 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.
Fri 12/56:25 amMKE - HHH
1 stop4h 57mAmerican Airlines
Fri 12/127:08 pmHHH - MKE
1 stop4h 53mAmerican Airlines
Deal found 11/11$431
This American Airlines deal was found by Cheapflights users on 11/12. 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 12/257:10 amMKE - HHH
1 stop6h 06mAmerican Airlines
Thu 1/16:13 pmHHH - MKE
1 stop6h 45mAmerican Airlines
Deal found 11/12$458
This American Airlines deal was found by Cheapflights users on 11/12. 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 12/257:10 amMKE - HHH
1 stop6h 06mAmerican Airlines
Wed 12/3111:14 amHHH - MKE
2 stops11h 17mAmerican Airlines
Deal found 11/12$494
This American Airlines deal was found by Cheapflights users on 11/11. 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.
Fri 11/146:00 amMKE - HHH
2 stops7h 57mAmerican Airlines
Sun 11/166:40 pmHHH - MKE
1 stop6h 22mAmerican Airlines
Deal found 11/11$528
This American Airlines deal was found by Cheapflights users on 11/11. 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.
Thu 11/137:10 amORD - HHH
1 stop6h 09mAmerican Airlines
Sun 11/162:51 pmHHH - ORD
1 stop5h 27mAmerican Airlines
Deal found 11/11$569

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 November 13, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$306
(American Airlines)

One-way from

$150
(American Airlines)

Popular in

March

Cheapest in

November

Average price

$208
Provider with most accurate pricing for Milwaukee-Mitchell-Hilton Head Island flight deals.
Search Deals
Provider most trusted by Cheapflights users for Milwaukee-Mitchell-Hilton Head Island flights.
Search Deals
From Wisconsin to Hilton Head Island
Search Deals
One-way flight from Wisconsin to Hilton Head Island
Search Deals
Highest demand for flights based on searches. 27% potential increase in price ($161 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 10% potential price decrease ($41 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2025
Search Deals

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 November 13, 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

Sat 2/7

8:50 pm-12:20 pm

2 stops14h 30m

Hilton Head Island

Sat 2/14

11:03 am-2:16 pm

1 stop4h 13m

$306

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Wed 1/7

8:12 am-2:59 pm

1 stop5h 47m

Hilton Head Island

Wed 1/14

3:29 pm-7:50 pm

1 stop5h 21m

$309

MinneapolisHilton Head Island

MSP - HHH

MSPHHH

Minneapolis St Paul

Thu 1/8

7:20 am-2:59 pm

1 stop6h 39m

Hilton Head Island

Sun 1/11

3:29 pm-9:26 pm

1 stop6h 57m

$319

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Mon 1/19

6:05 am-12:20 pm

1 stop5h 15m

Hilton Head Island

Sat 1/31

3:29 pm-7:50 pm

1 stop5h 21m

$336

MilwaukeeHilton Head Island

MKE - HHH

MKEHHH

Milwaukee-Mitchell

Thu 1/1

7:10 am-2:16 pm

1 stop6h 06m

Hilton Head Island

Sun 1/4

6:13 pm-11:58 pm

1 stop6h 45m

$338

MinneapolisHilton Head Island

MSP - HHH

MSPHHH

Minneapolis St Paul

Sun 2/8

7:20 am-2:59 pm

1 stop6h 39m

Hilton Head Island

Fri 2/13

4:14 pm-10:04 pm

1 stop6h 50m

$359

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Thu 2/5

6:05 am-12:20 pm

1 stop5h 15m

Hilton Head Island

Mon 2/9

3:29 pm-7:50 pm

1 stop5h 21m

$363

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Fri 1/30

6:05 am-12:20 pm

1 stop5h 15m

Hilton Head Island

Fri 2/6

3:29 pm-7:50 pm

1 stop5h 21m

$363

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Thu 11/27

5:00 am-10:24 am

1 stop4h 24m

Hilton Head Island

Mon 12/1

6:40 pm-11:40 pm

1 stop6h 00m

$367

MilwaukeeHilton Head Island

MKE - HHH

MKEHHH

Milwaukee-Mitchell

Sat 11/15

6:14 am-11:16 am

1 stop4h 02m

Hilton Head Island

Wed 11/19

1:02 pm-4:57 pm

1 stop4h 55m

$389

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/12

Showing 1-10 of 44 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 December 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.

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 November 13, 2025.

One of the essential ways to save on airfare from Wisconsin to Hilton Head Island is to remain as flexible as possible. Flights that are in the morning tend to be the most expensive. A flight in the evening could potentially save you up to 73% on airfare.

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 and United Airlines fly from Wisconsin to Hilton Head Island in about 6h 22m. The time it takes to get you to your destination can typically vary by up to 8h 08m. Airlines will cover a distance of 888 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 Milwaukee-Mitchell - Hilton Head Island or Minneapolis St Paul - 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 December 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
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 November 13, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$233Average$477FlexibilityNo cancel feeOn-time71%
DeltaCheapest$323Average$383FlexibilityNo cancel feeOn-timeN/A

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