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Hilton Head Island

$249+ 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 11/8. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — HHH
Oct 17 — Oct 241
Fri 10/17
Fri 10/24
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 September 17, 2025.

Round-trip from

$249
(American Airlines)

Popular in

March

Cheapest in

November

Average price

$313
From Milwaukee-Mitchell to Hilton Head Island
Search Deals
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 September 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 September 17, 2025.

This American Airlines deal was found by Cheapflights users on 9/14. 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 11/86:14 amMKE - HHH
1 stop7h 05mAmerican Airlines
Wed 11/127:07 pmHHH - MKE
1 stop4h 49mAmerican Airlines
Deal found 9/14$249
This American Airlines deal was found by Cheapflights users on 9/15. 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 9/15$274
This American Airlines deal was found by Cheapflights users on 9/16. 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 12/66:14 amMKE - HHH
1 stop6h 33mAmerican Airlines
Sun 12/146:52 pmHHH - MKE
1 stop6h 09mAmerican Airlines
Deal found 9/16$339
This American Airlines deal was found by Cheapflights users on 9/15. 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.
Sun 9/217:06 amMKE - HHH
1 stop6h 00mAmerican Airlines
Tue 9/305:20 pmHHH - MKE
1 stop6h 40mAmerican Airlines
Deal found 9/15$371

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 September 17, 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

Sat 11/8

6:14 am-2:19 pm

1 stop7h 05m

Hilton Head Island

Wed 11/12

7:07 pm-10:56 pm

1 stop4h 49m

$249

MilwaukeeHilton Head Island

MKE - HHH

MKEHHH

Milwaukee-Mitchell

Tue 2/3

7:17 am-2:18 pm

1 stop6h 01m

Hilton Head Island

Mon 2/9

6:14 pm-9:25 pm

1 stop4h 11m

$249

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

6:48 pm-12:01 am

1 stop6h 13m

$274

MilwaukeeHilton Head Island

MKE - HHH

MKEHHH

Milwaukee-Mitchell

Tue 10/14

10:55 am-11:16 am

2 stops23h 21m

$395

MilwaukeeHilton Head Island

MKE - HHH

MKEHHH

Milwaukee-Mitchell

Tue 10/14

10:35 am-3:30 pm

1 stop3h 55m

$420

MilwaukeeHilton Head Island

MKE - HHH

MKEHHH

Milwaukee-Mitchell

Thu 12/25

11:54 am-10:44 am

2 stops21h 50m

$458

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/15

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, January is the cheapest month in which you can book a flight from Milwaukee to Hilton Head Island (average of $275). Flying from Milwaukee 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.

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 September 17, 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
8.0
Very good
7,961 reviews

Boarding

8.2

Crew

8.5

Overall

8.0

Food

7.3

Comfort

7.9

Entertainment

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
7,961 reviews
Delta
8.0
Very good
7,961 reviews

Boarding

8.2

Crew

8.5

Overall

8.0

Food

7.3

Comfort

7.9

Entertainment

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
7,961 reviews

Boarding

8.2

Crew

8.5

Overall

8.0

Food

7.3

Comfort

7.9

Entertainment

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 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 7h 05m. 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.

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

    To fly one-way, consider booking your trip with United Airlines, which is currently one of the cheapest options available, starting at $395. Delta flights start at $420 while deals on American Airlines start at $458 one-way.

  • 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, January is the cheapest month in which you can book a flight from Milwaukee to Hilton Head Island (average of $275). Flying from Milwaukee 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 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 September 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$248Average$393FlexibilityNo cancel feeOn-time71%
DeltaCheapest$323Average$383FlexibilityNo cancel feeOn-timeN/A

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