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Hilton Head Island

$244+ 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 10/24. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — HHH
Aug 7 — Aug 141
Fri 8/7
Fri 8/14
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 July 8, 2026.

This American Airlines deal was found by Cheapflights users on 7/8. 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 11/146:14 am
MKE
-
HHH
1 stop7h 05m
American Airlines
Tue 11/172:51 pm
HHH
-
MKE
1 stop4h 10m
American Airlines
Deal found 7/8$285
This Delta deal was found by Cheapflights users on 7/8. 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 8/410:22 am
MKE
-
HHH
1 stop4h 10m
Delta
Tue 8/1112:15 pm
HHH
-
MKE
2 stops6h 53m
Delta
Deal found 7/8$290
This American Airlines deal was found by Cheapflights users on 7/6. 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 11/146:14 am
MKE
-
HHH
1 stop7h 05m
American Airlines
Wed 11/252:51 pm
HHH
-
MKE
1 stop4h 10m
American Airlines
Deal found 7/6$309
This American Airlines deal was found by Cheapflights users on 7/7. 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 7/215:02 am
MKE
-
HHH
1 stop7h 31m
American Airlines
Tue 7/284:55 pm
HHH
-
MKE
1 stop5h 59m
American Airlines
Deal found 7/7$324
This Delta deal was found by Cheapflights users on 7/6. 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 7/216:00 am
MKE
-
HHH
2 stops8h 29m
Delta
Tue 7/284:14 pm
HHH
-
MKE
1 stop7h 16m
Delta
Deal found 7/6$329
This Delta deal was found by Cheapflights users on 7/8. 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.
Sat 9/2610:03 am
MKE
-
HHH
1 stop4h 24m
Delta
Tue 10/64:10 pm
HHH
-
MKE
1 stop6h 39m
Delta
Deal found 7/8$330
This American Airlines deal was found by Cheapflights users on 7/6. 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 8/125:00 am
MKE
-
HHH
1 stop7h 17m
American Airlines
Sun 8/165:46 pm
HHH
-
MKE
1 stop7h 11m
American Airlines
Deal found 7/6$336
This United Airlines deal was found by Cheapflights users on 7/7. 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 8/298:30 am
MKE
-
HHH
1 stop4h 33m
United Airlines
Tue 9/12:58 pm
HHH
-
MKE
1 stop7h 02m
United Airlines
Deal found 7/7$341

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 July 8, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$285
(American Airlines)

One-way from

$244
(United Airlines)

Popular in

May

Cheapest in

January

Average price

$260
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
One-way flight from Milwaukee-Mitchell to Hilton Head Island
Search Deals
Highest demand for flights based on searches. 10% potential increase in price ($41 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($8 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 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 July 8, 2026.
Use the filters below to find and compare flights from Milwaukee to Hilton Head Island that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

MilwaukeeHilton Head Island

MKE - HHH

MKEHHH

Milwaukee-Mitchell

Tue 8/4

6:01 am-1:33 pm

1 stop6h 32m

Hilton Head Island

Tue 8/11

1:52 pm-7:59 pm

1 stop7h 07m

$285
Quickest round-trip

MilwaukeeHilton Head Island

MKE - HHH

MKEHHH

Milwaukee-Mitchell

Tue 8/4

10:22 am-3:32 pm

1 stop4h 10m

Hilton Head Island

Tue 8/11

12:15 pm-6:08 pm

2 stops6h 53m

$290

MilwaukeeHilton Head Island

MKE - HHH

MKEHHH

Milwaukee-Mitchell

Sat 9/26

10:03 am-3:27 pm

1 stop4h 24m

Hilton Head Island

Tue 10/6

4:10 pm-9:49 pm

1 stop6h 39m

$330

MilwaukeeHilton Head Island

MKE - HHH

MKEHHH

Milwaukee-Mitchell

Tue 7/21

6:00 am-3:29 pm

2 stops8h 29m

Hilton Head Island

Tue 7/28

12:11 pm-8:20 pm

2 stops9h 09m

$335

MilwaukeeHilton Head Island

MKE - HHH

MKEHHH

Milwaukee-Mitchell

Wed 8/12

5:00 am-1:17 pm

1 stop7h 17m

Hilton Head Island

Sun 8/16

5:46 pm-11:57 pm

1 stop7h 11m

$336
Cheapest one-way

MilwaukeeHilton Head Island

MKE - HHH

MKEHHH

Milwaukee-Mitchell

Sat 10/24

8:30 am-2:13 pm

1 stop4h 43m

$244

MilwaukeeHilton Head Island

MKE - HHH

MKEHHH

Milwaukee-Mitchell

Wed 8/12

6:00 am-1:17 pm

1 stop6h 17m

$244

MilwaukeeHilton Head Island

MKE - HHH

MKEHHH

Milwaukee-Mitchell

Fri 10/23

7:00 am-2:26 pm

1 stop6h 26m

$244

MilwaukeeHilton Head Island

MKE - HHH

MKEHHH

Milwaukee-Mitchell

Wed 8/12

6:00 am-3:32 pm

2 stops8h 32m

$249

MilwaukeeHilton Head Island

MKE - HHH

MKEHHH

Milwaukee-Mitchell

Sat 10/24

6:30 am-5:40 pm

2 stops10h 10m

$285

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/5

Showing 1-10 of 12 resultsSorted by cheapest first
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 July.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice 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.

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 July 8, 2026.
Read through reviews of airlines operating flights from Milwaukee to Hilton Head Island, such as American Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
American Airlines
7.1
Good
11,783 reviews

Overall

7.1

Boarding

7.5

Comfort

7.2

Entertainment

6.8

Crew

7.9

Food

6.4

Reviews

1 / 20
2.0
Mediocre

Anonymous,Apr 2026

DFW - BDL

They keep changing the gate, delaying the hours and then finally canceled it. No accomodation, no food, nothing!
American Airlines
7.1
Good
11,783 reviews
American Airlines
7.1
Good
11,783 reviews

Overall

7.1

Boarding

7.5

Comfort

7.2

Entertainment

6.8

Crew

7.9

Food

6.4

Reviews

1 / 20
2.0
Mediocre

Anonymous,Apr 2026

DFW - BDL

They keep changing the gate, delaying the hours and then finally canceled it. No accomodation, no food, nothing!

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 and Delta fly from Milwaukee to Hilton Head Island in about 4h 10m. The time it takes to get you to your destination can typically vary by up to 2h 22m. The distance from Milwaukee to Hilton Head Island is about 838 mi. This flight may include one or multiple stops.

  • What is the cheapest airline to fly 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. You may be able to fly from Milwaukee to Hilton Head Island for 27% less than the average price by searching for this airline.

  • 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.

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 airline flying from Milwaukee to Hilton Head Island

Discover the top airline 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 July 8, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$248Average$364FlexibilityNo cancel feeOn-time71%

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