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Hilton Head Island

$191+ Cheap flights from Milwaukee to Hilton Head Island (MKE - 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 2/24. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — HHH
Nov 23 — Nov 301
Sun 11/23
Sun 11/30
1 adult, Economy
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Cheap flight deals from Milwaukee to Hilton Head Island

Discover tips and strategies to find the most affordable flight options for your journey from Milwaukee (MKE) to Hilton Head Island (HHH). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated October 24, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$249
(American Airlines)

One-way from

$191
(American Airlines)

Popular in

March

Cheapest in

November

Average price

$404
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 Milwaukee-Mitchell to Hilton Head Island
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One-way flight from Milwaukee-Mitchell 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 October 2025
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Find flight deals from Milwaukee to Hilton Head Island

Cheapest flights from Milwaukee to Hilton Head Island
Explore the most affordable flight options available from Milwaukee to Hilton Head Island. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 24, 2025.

This American Airlines deal was found by Cheapflights users on 10/23. 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 10/23$249
This American Airlines deal was found by Cheapflights users on 10/23. 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 11/76:29 amMKE - HHH
1 stop5h 00mAmerican Airlines
Tue 11/117:07 pmHHH - MKE
1 stop4h 49mAmerican Airlines
Deal found 10/23$344
This American Airlines deal was found by Cheapflights users on 10/22. 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 11/146:29 amMKE - HHH
1 stop5h 00mAmerican Airlines
Tue 11/187:07 pmHHH - MKE
1 stop4h 49mAmerican Airlines
Deal found 10/22$371
This American Airlines deal was found by Cheapflights users on 10/23. 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 stops7h 35mAmerican Airlines
Deal found 10/23$431
This American Airlines deal was found by Cheapflights users on 10/23. 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 10/23$493

Cheapflights Fare Finder

 
Customize your flight search to find flights from Milwaukee 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 October 24, 2025.
Use the filters below to find and compare flights from Milwaukee to Hilton Head Island that are best for you.

Fly from

Milwaukee

Fly to

Hilton Head Island

Route

Depart

Return

Price

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

11:47 am-7:20 pm

2 stops8h 33m

$254

MilwaukeeHilton Head Island

MKE - HHH

MKEHHH

Milwaukee-Mitchell

Fri 11/7

6:29 am-12:29 pm

1 stop5h 00m

Hilton Head Island

Tue 11/11

7:07 pm-10:56 pm

1 stop4h 49m

$344

MilwaukeeHilton Head Island

MKE - HHH

MKEHHH

Milwaukee-Mitchell

Fri 11/14

6:29 am-12:29 pm

1 stop5h 00m

Hilton Head Island

Tue 11/18

7:07 pm-10:56 pm

1 stop4h 49m

$371

MilwaukeeHilton Head Island

MKE - HHH

MKEHHH

Milwaukee-Mitchell

Sun 1/18

6:13 am-12:20 pm

1 stop5h 07m

Hilton Head Island

Thu 1/22

3:29 pm-11:22 pm

2 stops8h 53m

$384

MilwaukeeHilton Head Island

MKE - HHH

MKEHHH

Milwaukee-Mitchell

Thu 12/25

7:10 am-2:16 pm

1 stop6h 06m

Hilton Head Island

Wed 12/31

11:14 am-5:49 pm

2 stops7h 35m

$431

MilwaukeeHilton Head Island

MKE - HHH

MKEHHH

Milwaukee-Mitchell

Mon 4/6

6:27 am-2:19 pm

2 stops6h 52m

Hilton Head Island

Fri 4/10

6:07 pm-9:12 pm

1 stop4h 05m

$452

MilwaukeeHilton Head Island

MKE - HHH

MKEHHH

Milwaukee-Mitchell

Tue 4/21

6:00 am-3:18 pm

2 stops8h 18m

Hilton Head Island

Wed 4/22

4:00 pm-8:52 pm

1 stop5h 52m

$467

MilwaukeeHilton Head Island

MKE - HHH

MKEHHH

Milwaukee-Mitchell

Wed 2/25

7:12 am-2:16 pm

1 stop6h 04m

$191

MilwaukeeHilton Head Island

MKE - HHH

MKEHHH

Milwaukee-Mitchell

Wed 11/19

5:00 am-2:57 pm

2 stops8h 57m

$192

MilwaukeeHilton Head Island

MKE - HHH

MKEHHH

Milwaukee-Mitchell

Tue 11/18

6:12 am-6:37 pm

2 stops11h 25m

$227

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/23

Showing 1-10 of 14 results
1
2

Compare providers for flights from Milwaukee to Hilton Head Island

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Milwaukee to Hilton Head Island in October.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Milwaukee-Hilton Head Island flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Milwaukee-Hilton Head Island flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Milwaukee-Hilton Head Island flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Milwaukee-Hilton Head Island flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Milwaukee-Hilton Head Island flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Milwaukee to Hilton Head Island

Have a flexible travel schedule? Discover the best time to fly to Hilton Head Island from Milwaukee 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 Milwaukee to Hilton Head Island

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

Currently, May is the cheapest month in which you can book a flight from Milwaukee to Hilton Head Island (average of $46). Flying from Milwaukee 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.

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 October 24, 2025.
Read through reviews of airlines operating flights from Milwaukee to Hilton Head Island, such as Delta and American Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.9
Good
7,982 reviews

Food

7.3

Comfort

7.9

Entertainment

7.9

Boarding

8.2

Crew

8.5

Overall

7.9

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
Delta
7.9
Good
7,982 reviews
Delta
7.9
Good
7,982 reviews

Food

7.3

Comfort

7.9

Entertainment

7.9

Boarding

8.2

Crew

8.5

Overall

7.9

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
American Airlines
7.2
Good
11,032 reviews
Delta
7.9
Good
7,982 reviews

Food

7.3

Comfort

7.9

Entertainment

7.9

Boarding

8.2

Crew

8.5

Overall

7.9

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.

Related info for your journey

Find useful and relevant information for your journey from Milwaukee 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.

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

    Airlines like American Airlines fly from Milwaukee to Hilton Head Island in about 5h 01m. The time it takes to get you to your destination can typically vary by up to . The distance from Milwaukee to Hilton Head Island is about 838 mi.

  • What are the cheapest airlines flying from Milwaukee to Hilton Head Island round-trip?

    Flying on American Airlines is currently your cheapest option to Hilton Head Island, with prices starting at $248. Another option worth looking into is Delta, starting at $323 round trip. You may be able to fly from Milwaukee to Hilton Head Island for 48% less than the average price by searching for these airlines.

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

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

  • How can I find direct flights from Milwaukee 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 Milwaukee to Hilton Head Island.

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

    Yes. Cheapflights offers flight deals from Milwaukee 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 Milwaukee to Hilton Head Island?

    Currently, May is the cheapest month in which you can book a flight from Milwaukee to Hilton Head Island (average of $46). Flying from Milwaukee 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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Top 2 airlines flying from Milwaukee to Hilton Head Island

Discover the top 2 airlines that operate flights from Milwaukee 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 October 24, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$248Average$392FlexibilityNo cancel feeOn-time71%
DeltaCheapest$323Average$383FlexibilityNo cancel feeOn-timeN/A

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