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$189+ Cheap flights from Hilton Head Island to Milwaukee (HHH - MKE)

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 5/19. Fares are subject to change and may not be available on all flights or dates of travel.
HHH — MKE
Mar 22 — Mar 291
Sun 3/22
Sun 3/29
1 adult, Economy
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Cheap flight deals from Hilton Head Island to Milwaukee

Cheapest flights from Hilton Head Island to Milwaukee
Explore the most affordable flight options available from Hilton Head Island to Milwaukee. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 20, 2026.

This United Airlines deal was found by Cheapflights users on 2/20. 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 4/13:05 pm
HHH
-
MKE
1 stop7h 13m
United Airlines
Mon 4/66:50 am
MKE
-
HHH
1 stop6h 26m
United Airlines
Deal found 2/20$274
This United Airlines deal was found by Cheapflights users on 2/20. 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.
Fri 7/33:05 pm
HHH
-
MKE
1 stop4h 46m
United Airlines
Tue 7/77:30 am
MKE
-
HHH
1 stop5h 51m
United Airlines
Deal found 2/20$289
This American Airlines deal was found by Cheapflights users on 2/20. 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 4/12:58 pm
HHH
-
MKE
2 stops9h 26m
American Airlines
Mon 4/67:06 am
MKE
-
HHH
1 stop6h 16m
American Airlines
Deal found 2/20$334
This American Airlines deal was found by Cheapflights users on 2/17. 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 4/184:10 pm
HHH
-
MKE
1 stop6h 13m
American Airlines
Mon 4/2012:00 pm
MKE
-
HHH
1 stop5h 09m
American Airlines
Deal found 2/17$346
This American Airlines deal was found by Cheapflights users on 2/17. 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 4/184:10 pm
HHH
-
MKE
1 stop6h 13m
American Airlines
Tue 4/215:06 am
MKE
-
HHH
2 stops8h 18m
American Airlines
Deal found 2/17$351
This American Airlines deal was found by Cheapflights users on 2/20. 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 2/216:20 pm
HHH
-
MKE
1 stop6h 35m
American Airlines
Sat 2/288:00 am
MKE
-
HHH
2 stops8h 44m
American Airlines
Deal found 2/20$359

Find flight deals from Hilton Head Island to Milwaukee

Discover tips and strategies to find the most affordable flight options for your journey from Hilton Head Island (HHH) to Milwaukee (MKE). 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 February 20, 2026.

Round-trip from

$274
(United Airlines)

One-way from

$189
(Delta)
From Hilton Head Island to Milwaukee-Mitchell
Search Deals
One-way flight from Hilton Head Island to Milwaukee-Mitchell
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Cheapflights Fare Finder

 
Customize your flight search to find flights from Hilton Head Island to Milwaukee 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 February 20, 2026.
Use the filters below to find and compare flights from Hilton Head Island to Milwaukee that are best for you.

Fly from

Hilton Head Island

Fly to

Milwaukee

Route

Depart

Return

Price

Hilton Head IslandMilwaukee

HHH - MKE

HHHMKE

Hilton Head Island

Wed 4/1

3:05 pm-9:18 pm

1 stop7h 13m

Milwaukee-Mitchell

Mon 4/6

6:50 am-2:16 pm

1 stop6h 26m

$274

Hilton Head IslandMilwaukee

HHH - MKE

HHHMKE

Hilton Head Island

Wed 4/1

2:58 pm-11:24 pm

2 stops9h 26m

Milwaukee-Mitchell

Mon 4/6

7:06 am-2:22 pm

1 stop6h 16m

$334

Hilton Head IslandMilwaukee

HHH - MKE

HHHMKE

Hilton Head Island

Sat 4/18

4:10 pm-9:23 pm

1 stop6h 13m

Milwaukee-Mitchell

Mon 4/20

12:00 pm-6:09 pm

1 stop5h 09m

$346

Hilton Head IslandMilwaukee

HHH - MKE

HHHMKE

Hilton Head Island

Wed 4/1

3:05 pm-9:18 pm

1 stop7h 13m

Milwaukee-Mitchell

Sat 4/4

7:22 pm-2:16 pm

1 stop17h 54m

$464

Hilton Head IslandMilwaukee

HHH - MKE

HHHMKE

Hilton Head Island

Sun 3/29

3:00 pm-9:49 pm

1 stop7h 49m

Milwaukee-Mitchell

Tue 3/31

6:50 am-2:06 pm

1 stop6h 16m

$482

Hilton Head IslandMilwaukee

HHH - MKE

HHHMKE

Hilton Head Island

Wed 4/1

3:05 pm-9:18 pm

1 stop7h 13m

Milwaukee-Mitchell

Thu 4/2

8:30 am-2:16 pm

1 stop4h 46m

$482

Hilton Head IslandMilwaukee

HHH - MKE

HHHMKE

Hilton Head Island

Sat 3/28

4:31 pm-11:24 pm

1 stop7h 53m

Milwaukee-Mitchell

Tue 3/31

6:05 am-4:44 pm

2 stops9h 39m

$530

Hilton Head IslandMilwaukee

HHH - MKE

HHHMKE

Hilton Head Island

Wed 4/1

6:15 pm-11:45 pm

1 stop6h 30m

Milwaukee-Mitchell

Sat 4/4

8:31 am-5:44 pm

2 stops8h 13m

$571

Hilton Head IslandMilwaukee

HHH - MKE

HHHMKE

Hilton Head Island

Wed 4/1

6:15 pm-11:45 pm

1 stop6h 30m

Milwaukee-Mitchell

Fri 4/3

11:22 am-5:44 pm

1 stop5h 22m

$585

Hilton Head IslandMilwaukee

HHH - MKE

HHHMKE

Hilton Head Island

Tue 5/19

4:05 pm-10:28 pm

1 stop7h 23m

$189

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/20

Showing 1-10 of 13 results
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Best time to book a flight from Hilton Head Island to Milwaukee

Have a flexible travel schedule? Discover the best time to fly to Milwaukee from Hilton Head Island 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 Hilton Head Island to Milwaukee

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

Currently, April is the cheapest month in which you can book a flight from Hilton Head Island to Milwaukee (average of $76). Flying from Hilton Head Island to Milwaukee in February is currently the most expensive (average of $257). 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.

Related info for your journey

Find useful and relevant information for your journey from Hilton Head Island to Milwaukee. 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 Hilton Head Island to Milwaukee?

    Departing from Hilton Head Island to Milwaukee will take you 4h 46m. The distance between Hilton Head Island and Milwaukee is about 838 mi. Both multi-stop and nonstop flights can be found to your destination and back.

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

    Yes. In addition to deals on Hilton Head Island to Milwaukee flights, Cheapflights offers vacation packages that include both flights and hotel.

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

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Hilton Head Island to Milwaukee.

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

    Yes. Cheapflights offers flight deals from Hilton Head Island to Milwaukee 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 Hilton Head Island to Milwaukee?

    Currently, April is the cheapest month in which you can book a flight from Hilton Head Island to Milwaukee (average of $76). Flying from Hilton Head Island to Milwaukee in February is currently the most expensive (average of $257). 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 Milwaukee?

Book flights to Milwaukee if you plan to visit one of these locations
Sheboygan
New Berlin
Oak Creek
Wauwatosa

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