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 $279. Another option worth looking into is Delta, starting at $321 round trip. You may be able to fly from Milwaukee to Hilton Head Island for 41% less than the average price by searching for these airlines.

What is the cheapest day to fly from Milwaukee to Hilton Head Island?

Travelers seeking maximum savings on their Milwaukee to Hilton Head Island flight should consider departing on Wednesday mornings when fares are most often at their lowest. Thursday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

In terms of precipitation, rainfall in Hilton Head Island ranges from 2.4 - 7.8 inches per month. August is typically the wettest month, when rainfall can reach 7.8 in. November is typically the driest time to visit Hilton Head Island when rainfall is around 2.4 in.

If weather is an important factor for your trip to Hilton Head Island, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 80.6 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 50.0 F).

What is the cheapest day to fly round-trip from Milwaukee to Hilton Head Island?

Wednesday flights are generally found to be more expensive for flights from Milwaukee to Hilton Head Island. This shouldn’t discourage you from searching, as you can still find great deals by being flexible with your options. Use our search form to find deals on tickets to Hilton Head Island.

What is the cheapest month to fly from Milwaukee to Hilton Head Island?

November is one of the best times of the year to fly to Hilton Head Island from Milwaukee. Prices for November average $478 per person but you can even find prices for as low as $216. The most expensive prices can be found in the month of March. Opting for a November flight can save you 173% on your journey compared to booking in March

What is the cheapest time of day to fly from MKE to HHH?

When flying from Milwaukee to Hilton Head Island, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

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.

$142+ Flights from Milwaukee to Hilton Head Island

Home Search by date Vacation packages Hotels Flight deals Car rental Travel tips & news

Find cheap flights from Milwaukee to Hilton Head Island with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap flight deals from Milwaukee to Hilton Head Island

Round-trip from	$279 (American Airlines)
One-way from	$142 (Delta)
Popular in	March
Cheapest in	November
Average price	$442

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. 34% potential increase in price ($251 potential increase over avg. RT price).

Search Deals

Cheapest flight prices on average. 18% potential price decrease ($76 potential savings vs. average RT price).

Search Deals

Average for round-trip flights in July 2025

Search Deals

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 julio 3, 2025.

mar. 10/216:13 amMKE - HHH

2 stops9h 42mAmerican Airlines

mié. 10/295:25 pmHHH - MKE

1 stop6h 48mAmerican Airlines

Deal found 7/1

$254

dom. 9/217:05 amMKE - HHH

1 stop7h 17mDelta

mar. 9/304:05 pmHHH - MKE

1 stop6h 52mDelta

Deal found 7/3

$321

Best flights from Milwaukee to Hilton Head Island
Discover carefully curated flight deals from Milwaukee to Hilton Head Island that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated julio 3, 2025.

dom. 9/215:05 amMKE - HHH

2 stops8h 01mAmerican Airlines

mar. 9/305:20 pmHHH - MKE

1 stop6h 40mAmerican Airlines

Deal found 7/1

$279

dom. 9/217:05 amMKE - HHH

1 stop7h 17mDelta

mar. 9/304:05 pmHHH - MKE

1 stop6h 52mDelta

Deal found 7/3

$321

Last-minute flights from Milwaukee to Hilton Head Island
Discover last-minute flight deals from Milwaukee to Hilton Head Island. Data last updated julio 3, 2025 and is based on user searches.

mié. 7/166:05 amMKE - HHH

1 stop5h 41mAmerican Airlines

dom. 7/206:06 pmHHH - MKE

1 stop6h 58mAmerican Airlines

Deal found 7/1

$371

One-way flights from Milwaukee to Hilton Head Island
Search for one-way flight options from Milwaukee to Hilton Head Island. Find affordable one-way fares based on user searches. Data last updated julio 3, 2025.

mié. 9/177:05 amMKE - HHH

1 stop7h 17mDelta

Deal found 7/2

$142

mié. 10/298:00 amMKE - HHH

1 stop6h 02mAmerican Airlines

Deal found 7/1

$165

Cheapflights Fare Finder

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

MilwaukeeHilton Head Island

MKE - HHH

MKEHHH

Milwaukee-Mitchell

mar. 10/21

6:13 am-4:55 pm

2 stops9h 42m

Hilton Head Island

mié. 10/29

5:25 pm-11:13 pm

1 stop6h 48m

$254

MilwaukeeHilton Head Island

MKE - HHH

MKEHHH

Milwaukee-Mitchell

dom. 9/21

7:05 am-3:22 pm

1 stop7h 17m

Hilton Head Island

mar. 9/30

4:05 pm-9:57 pm

1 stop6h 52m

$321

MilwaukeeHilton Head Island

MKE - HHH

MKEHHH

Milwaukee-Mitchell

mié. 9/17

7:05 am-3:22 pm

1 stop7h 17m

$142

MilwaukeeHilton Head Island

MKE - HHH

MKEHHH

Milwaukee-Mitchell

mié. 10/29

8:00 am-3:02 pm

1 stop6h 02m

$165

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/2

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

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

7,982 reviews

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

7,982 reviews

Delta

8.0

Very good

7,982 reviews

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

7,982 reviews

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

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 $279. Another option worth looking into is Delta, starting at $321 round trip. You may be able to fly from Milwaukee to Hilton Head Island for 41% 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, 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

Beaufort

Bluffton

Browse thousands of different options on Cheapflights for your next trip

Top 2 airlines flying from Milwaukee to Hilton Head Island

Airline	Cheapest	Average	Flexibility	On-time
American Airlines	Cheapest$221	Average$380	FlexibilityNo cancel fee	On-time71%
Delta	Cheapest$253	Average$419	FlexibilityNo cancel fee	On-timeN/A

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.

$142+ 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 9/17. Fares are subject to change and may not be available on all flights or dates of travel.

Find cheap flights from Milwaukee to Hilton Head Island with Cheapflights

1. Tell us where you want to go

2. Select your favorite providers

3. Compare prices and book

Cheap flight deals from Milwaukee to Hilton Head Island

Round-trip from

One-way from

Popular in

Cheapest in

Average price

Find flight deals from Milwaukee to Hilton Head Island

Cheapest flights from Milwaukee to Hilton Head IslandExplore 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 julio 3, 2025.

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 julio 3, 2025.

Cheapflights Fare Finder

Use the filters below to find and compare flights from Milwaukee to Hilton Head Island that are best for you.

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.

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?

Reviews of airlines servicing Hilton Head Island

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.

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.

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

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

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

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

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

Traveling to a place near Milwaukee?

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Milwaukee to Hilton Head Island

See prices for flight routes from nearby airports that may be better suited for you.

Top 2 airlines flying from Milwaukee to Hilton Head Island

100% Free

Book with Flexibility

Travel Smart

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 julio 3, 2025.