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Hilton Head Island

$269+ Cheap flights from Milwaukee to Hilton Head Island (MKE - HHH)

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 2/11. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — HHH
Feb 20 — Feb 271
Fri 2/20
Fri 2/27
1 adult, Economy
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Cheap 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 January 21, 2026.

This American Airlines deal was found by Cheapflights users on 1/21. 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 2/116:06 am
MKE
-
HHH
1 stop5h 14m
American Airlines
Sun 2/156:20 pm
HHH
-
MKE
1 stop6h 35m
American Airlines
Deal found 1/21$269
This American Airlines deal was found by Cheapflights users on 1/20. 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 5/25:00 am
MKE
-
HHH
2 stops10h 34m
American Airlines
Wed 5/65:04 pm
HHH
-
MKE
1 stop6h 43m
American Airlines
Deal found 1/20$281
This American Airlines deal was found by Cheapflights users on 1/21. 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 2/185:00 am
MKE
-
HHH
2 stops9h 01m
American Airlines
Wed 2/253:31 pm
HHH
-
MKE
1 stop7h 10m
American Airlines
Deal found 1/21$299
This United Airlines deal was found by Cheapflights users on 1/20. 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.
Wed 4/17:50 am
MKE
-
HHH
1 stop5h 16m
United Airlines
Thu 4/93:00 pm
HHH
-
MKE
1 stop7h 49m
United Airlines
Deal found 1/20$355
This American Airlines deal was found by Cheapflights users on 1/20. 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 4/16:05 am
MKE
-
HHH
2 stops7h 17m
American Airlines
Thu 4/91:08 pm
HHH
-
MKE
1 stop5h 43m
American Airlines
Deal found 1/20$360
This American Airlines deal was found by Cheapflights users on 1/20. 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 4/285:00 am
MKE
-
HHH
2 stops6h 37m
American Airlines
Tue 5/511:17 am
HHH
-
MKE
2 stops11h 42m
American Airlines
Deal found 1/20$373
This American Airlines deal was found by Cheapflights users on 1/20. 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 5/26:10 am
MKE
-
HHH
2 stops9h 24m
American Airlines
Sat 5/95:04 pm
HHH
-
MKE
1 stop6h 43m
American Airlines
Deal found 1/20$374

Find 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 January 21, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

Expedia
3 stars

Round-trip from

$269
(American Airlines)

Popular in

April

Cheapest in

January

Average price

$238
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 Milwaukee-Mitchell to Hilton Head Island
Search Deals
Highest demand for flights based on searches. 14% potential increase in price ($67 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($14 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals

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 January 21, 2026.
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

Wed 2/11

6:06 am-12:20 pm

1 stop5h 14m

Hilton Head Island

Sun 2/15

6:20 pm-11:55 pm

1 stop6h 35m

$269

MilwaukeeHilton Head Island

MKE - HHH

MKEHHH

Milwaukee-Mitchell

Tue 4/28

6:39 am-12:37 pm

1 stop4h 58m

Hilton Head Island

Tue 5/5

11:17 am-4:39 pm

1 stop6h 22m

$269

MilwaukeeHilton Head Island

MKE - HHH

MKEHHH

Milwaukee-Mitchell

Sat 5/2

5:00 am-4:34 pm

2 stops10h 34m

Hilton Head Island

Wed 5/6

5:04 pm-10:47 pm

1 stop6h 43m

$281

MilwaukeeHilton Head Island

MKE - HHH

MKEHHH

Milwaukee-Mitchell

Wed 2/18

5:00 am-3:01 pm

2 stops9h 01m

Hilton Head Island

Wed 2/25

3:31 pm-9:41 pm

1 stop7h 10m

$299

MilwaukeeHilton Head Island

MKE - HHH

MKEHHH

Milwaukee-Mitchell

Wed 4/1

7:50 am-2:06 pm

1 stop5h 16m

Hilton Head Island

Thu 4/9

3:00 pm-9:49 pm

1 stop7h 49m

$355

MilwaukeeHilton Head Island

MKE - HHH

MKEHHH

Milwaukee-Mitchell

Wed 4/1

11:22 am-5:44 pm

1 stop5h 22m

Hilton Head Island

Thu 4/9

6:39 pm-10:47 pm

1 stop5h 08m

$355

MilwaukeeHilton Head Island

MKE - HHH

MKEHHH

Milwaukee-Mitchell

Sat 5/2

6:10 am-4:34 pm

2 stops9h 24m

Hilton Head Island

Sat 5/9

5:04 pm-10:47 pm

1 stop6h 43m

$374

MilwaukeeHilton Head Island

MKE - HHH

MKEHHH

Milwaukee-Mitchell

Sat 3/28

6:00 am-2:22 pm

1 stop7h 22m

$468

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/20

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 January.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star

*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 Expedia the most. Expedia 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.

How much does it cost to fly round-trip from Milwaukee to Hilton Head Island?

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 January 21, 2026.
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
8,088 reviews

Boarding

8.1

Overall

7.9

Comfort

7.9

Crew

8.5

Entertainment

7.8

Food

7.2

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Delta
7.9
Good
8,088 reviews
Delta
7.9
Good
8,088 reviews

Boarding

8.1

Overall

7.9

Comfort

7.9

Crew

8.5

Entertainment

7.8

Food

7.2

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
American Airlines
7.2
Good
11,174 reviews
Delta
7.9
Good
8,088 reviews

Boarding

8.1

Overall

7.9

Comfort

7.9

Crew

8.5

Entertainment

7.8

Food

7.2

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.

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 14m. 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 Delta is currently your cheapest option to Hilton Head Island, with prices starting at $223. Another option worth looking into is American Airlines, starting at $248 round trip. You may be able to fly from Milwaukee to Hilton Head Island for 43% 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

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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 January 21, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$223Average$383FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$248Average$427FlexibilityNo cancel feeOn-time71%

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