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Hilton Head Island

$253+ 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 9/4. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — HHH
Jun 22 — Jun 291
Mon 6/22
Mon 6/29
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 May 23, 2026.

This American Airlines deal was found by Cheapflights users on 5/22. 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.
Tue 7/217:00 am
MKE
-
HHH
1 stop6h 16m
American Airlines
Tue 7/282:03 pm
HHH
-
MKE
1 stop5h 20m
American Airlines
Deal found 5/22$261
This American Airlines deal was found by Cheapflights users on 5/21. 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.
Fri 6/56:00 am
MKE
-
HHH
2 stops9h 32m
American Airlines
Tue 6/92:02 pm
HHH
-
MKE
1 stop5h 18m
American Airlines
Deal found 5/21$344
This American Airlines deal was found by Cheapflights users on 5/22. 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 6/195:00 am
MKE
-
HHH
1 stop7h 32m
American Airlines
Fri 6/2611:40 am
HHH
-
MKE
2 stops10h 25m
American Airlines
Deal found 5/22$365
This American Airlines deal was found by Cheapflights users on 5/21. 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.
Sat 6/137:00 am
MKE
-
HHH
1 stop4h 26m
American Airlines
Fri 6/192:02 pm
HHH
-
MKE
1 stop6h 56m
American Airlines
Deal found 5/21$370
This American Airlines deal was found by Cheapflights users on 5/21. 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.
Sat 6/66:00 am
MKE
-
HHH
2 stops9h 34m
American Airlines
Fri 6/122:02 pm
HHH
-
MKE
1 stop5h 18m
American Airlines
Deal found 5/21$375
This American Airlines deal was found by Cheapflights users on 5/23. 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 6/46:13 am
MKE
-
HHH
1 stop6h 19m
American Airlines
Sun 6/712:56 pm
HHH
-
MKE
2 stops9h 09m
American Airlines
Deal found 5/23$380
This United Airlines deal was found by Cheapflights users on 5/23. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/157:20 am
MKE
-
HHH
1 stop5h 43m
United Airlines
Fri 8/212:48 pm
HHH
-
MKE
1 stop7h 12m
United Airlines
Deal found 5/23$382

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 May 23, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$261
(American Airlines)

One-way from

$253
(Delta)

Popular in

July

Cheapest in

January

Average price

$412
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. 7% potential increase in price ($26 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($13 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 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 May 23, 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 7/21

5:02 am-1:33 pm

1 stop7h 31m

Hilton Head Island

Tue 7/28

11:47 am-5:37 pm

1 stop6h 50m

$261

MilwaukeeHilton Head Island

MKE - HHH

MKEHHH

Milwaukee-Mitchell

Fri 6/5

6:00 am-4:32 pm

2 stops9h 32m

Hilton Head Island

Tue 6/9

2:02 pm-6:20 pm

1 stop5h 18m

$344

MilwaukeeHilton Head Island

MKE - HHH

MKEHHH

Milwaukee-Mitchell

Wed 6/17

7:00 am-2:13 pm

1 stop6h 13m

Hilton Head Island

Mon 6/22

11:40 am-5:37 pm

1 stop6h 57m

$370

MilwaukeeHilton Head Island

MKE - HHH

MKEHHH

Milwaukee-Mitchell

Sat 6/6

6:00 am-4:34 pm

2 stops9h 34m

Hilton Head Island

Fri 6/12

2:02 pm-6:20 pm

1 stop5h 18m

$375

MilwaukeeHilton Head Island

MKE - HHH

MKEHHH

Milwaukee-Mitchell

Sat 8/15

7:20 am-2:03 pm

1 stop5h 43m

Hilton Head Island

Fri 8/21

2:48 pm-9:00 pm

1 stop7h 12m

$382

MilwaukeeHilton Head Island

MKE - HHH

MKEHHH

Milwaukee-Mitchell

Thu 6/4

6:00 am-4:32 pm

2 stops9h 32m

Hilton Head Island

Sun 6/7

12:56 pm-9:05 pm

2 stops9h 09m

$386
Quickest round-trip

MilwaukeeHilton Head Island

MKE - HHH

MKEHHH

Milwaukee-Mitchell

Sun 6/21

6:13 am-1:32 pm

1 stop6h 19m

Hilton Head Island

Mon 6/29

2:02 pm-6:20 pm

1 stop5h 18m

$389
Cheapest one-way

MilwaukeeHilton Head Island

MKE - HHH

MKEHHH

Milwaukee-Mitchell

Fri 9/4

7:00 am-3:20 pm

1 stop7h 20m

$253

MilwaukeeHilton Head Island

MKE - HHH

MKEHHH

Milwaukee-Mitchell

Sat 9/5

6:15 am-2:03 pm

1 stop6h 48m

$269
Quickest one-way

MilwaukeeHilton Head Island

MKE - HHH

MKEHHH

Milwaukee-Mitchell

Fri 5/29

8:35 am-2:21 pm

1 stop4h 46m

$282

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/22

Showing 1-10 of 11 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 May.
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.

Cheapflights Insights

Everything you need to know about your flight from Milwaukee to Hilton Head Island

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 May 23, 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
8,444 reviews

Food

7.2

Boarding

8.1

Entertainment

7.8

Comfort

7.8

Overall

7.9

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Anonymous,May 2026

SEA - KOA

The snacks were not very good, not everyone was very friendly and professional
Delta
7.9
Good
8,444 reviews
Delta
7.9
Good
8,444 reviews

Food

7.2

Boarding

8.1

Entertainment

7.8

Comfort

7.8

Overall

7.9

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Anonymous,May 2026

SEA - KOA

The snacks were not very good, not everyone was very friendly and professional
American Airlines
7.1
Good
11,640 reviews
Delta
7.9
Good
8,444 reviews

Food

7.2

Boarding

8.1

Entertainment

7.8

Comfort

7.8

Overall

7.9

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Anonymous,May 2026

SEA - KOA

The snacks were not very good, not everyone was very friendly and professional

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 15m. 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 $260 round trip. You may be able to fly from Milwaukee to Hilton Head Island for 29% 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.

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 May 23, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$248Average$346FlexibilityNo cancel feeOn-time71%
DeltaCheapest$260Average$364FlexibilityNo cancel feeOn-timeN/A

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