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$259+ Cheap flights from Hilton Head Island to Milwaukee (HHH - MKE)

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 10/21. Fares are subject to change and may not be available on all flights or dates of travel.
HHH — MKE
Nov 5 — Nov 121
Wed 11/5
Wed 11/12
1 adult, Economy
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Cheap 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 October 6, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$319
(American Airlines)
Provider with most accurate pricing for Hilton Head Island-Milwaukee-Mitchell flight deals.
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Provider most trusted by Cheapflights users for Hilton Head Island-Milwaukee-Mitchell flights.
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From Hilton Head Island to Milwaukee-Mitchell
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Find 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 October 6, 2025.

This American Airlines deal was found by Cheapflights users on 10/6. 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.
Tue 10/215:21 pmHHH - MKE
1 stop6h 55mAmerican Airlines
Sat 10/257:12 amMKE - HHH
1 stop6h 20mAmerican Airlines
Deal found 10/6$259
This American Airlines deal was found by Cheapflights users on 10/5. 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 11/47:07 pmHHH - MKE
1 stop4h 49mAmerican Airlines
Sat 11/86:14 amMKE - HHH
1 stop4h 02mAmerican Airlines
Deal found 10/5$319
This American Airlines deal was found by Cheapflights users on 10/5. 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 11/43:27 pmHHH - MKE
2 stops9h 15mAmerican Airlines
Sun 11/96:14 amMKE - HHH
1 stop7h 05mAmerican Airlines
Deal found 10/5$324
This American Airlines deal was found by Cheapflights users on 10/5. 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 11/43:27 pmHHH - MKE
2 stops9h 15mAmerican Airlines
Mon 11/106:00 amMKE - HHH
2 stops7h 57mAmerican Airlines
Deal found 10/5$329
This American Airlines deal was found by Cheapflights users on 10/5. 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 11/11:55 pmHHH - MKE
1 stop6h 51mAmerican Airlines
Wed 11/55:00 amMKE - HHH
2 stops8h 57mAmerican Airlines
Deal found 10/5$374
This American Airlines deal was found by Cheapflights users on 10/5. 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.
Mon 11/37:07 pmHHH - MKE
1 stop4h 49mAmerican Airlines
Tue 11/45:00 amMKE - HHH
2 stops8h 57mAmerican Airlines
Deal found 10/5$448
This American Airlines deal was found by Cheapflights users on 10/5. 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 11/612:19 pmHHH - MKE
2 stops10h 12mAmerican Airlines
Sat 11/88:05 amMKE - HHH
2 stops9h 12mAmerican Airlines
Deal found 10/5$451
This American Airlines deal was found by Cheapflights users on 10/5. 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 11/11:55 pmHHH - MKE
1 stop6h 51mAmerican Airlines
Thu 11/66:14 amMKE - HHH
1 stop4h 35mAmerican Airlines
Deal found 10/5$478

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 October 6, 2025.
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

Tue 10/21

5:21 pm-11:16 pm

1 stop6h 55m

Milwaukee-Mitchell

Sat 10/25

7:12 am-2:32 pm

1 stop6h 20m

$259

Hilton Head IslandMilwaukee

HHH - MKE

HHHMKE

Hilton Head Island

Tue 11/4

7:07 pm-10:56 pm

1 stop4h 49m

Milwaukee-Mitchell

Mon 11/10

6:29 am-12:29 pm

1 stop5h 00m

$319

Hilton Head IslandMilwaukee

HHH - MKE

HHHMKE

Hilton Head Island

Tue 11/4

7:07 pm-10:56 pm

1 stop4h 49m

Milwaukee-Mitchell

Sun 11/9

6:14 am-2:19 pm

1 stop7h 05m

$319

Hilton Head IslandMilwaukee

HHH - MKE

HHHMKE

Hilton Head Island

Wed 11/5

7:07 pm-10:56 pm

1 stop4h 49m

Milwaukee-Mitchell

Mon 11/10

6:29 am-12:29 pm

1 stop5h 00m

$319

Hilton Head IslandMilwaukee

HHH - MKE

HHHMKE

Hilton Head Island

Wed 11/5

7:07 pm-10:56 pm

1 stop4h 49m

Milwaukee-Mitchell

Sat 11/8

6:14 am-11:16 am

1 stop4h 02m

$319

Hilton Head IslandMilwaukee

HHH - MKE

HHHMKE

Hilton Head Island

Thu 11/6

6:40 pm-12:02 am

1 stop6h 22m

Milwaukee-Mitchell

Sat 11/8

6:14 am-11:16 am

1 stop4h 02m

$319

Hilton Head IslandMilwaukee

HHH - MKE

HHHMKE

Hilton Head Island

Thu 11/6

6:40 pm-12:02 am

1 stop6h 22m

Milwaukee-Mitchell

Mon 11/10

6:29 am-12:29 pm

1 stop5h 00m

$319

Hilton Head IslandMilwaukee

HHH - MKE

HHHMKE

Hilton Head Island

Tue 11/4

3:27 pm-11:42 pm

2 stops9h 15m

Milwaukee-Mitchell

Sat 11/8

6:14 am-11:16 am

1 stop4h 02m

$324

Hilton Head IslandMilwaukee

HHH - MKE

HHHMKE

Hilton Head Island

Thu 11/6

6:40 pm-12:02 am

1 stop6h 22m

Milwaukee-Mitchell

Sun 11/9

5:00 am-2:19 pm

2 stops8h 19m

$324

Hilton Head IslandMilwaukee

HHH - MKE

HHHMKE

Hilton Head Island

Wed 11/5

1:02 pm-10:09 pm

2 stops10h 07m

Milwaukee-Mitchell

Sun 11/9

6:14 am-2:19 pm

1 stop7h 05m

$324

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/6

Showing 1-10 of 11 results
1
2
  • Most accurate provider: When it comes to deals on Hilton Head Island-Milwaukee flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Hilton Head Island-Milwaukee flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Hilton Head Island-Milwaukee flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Hilton Head Island-Milwaukee 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 Hilton Head Island-Milwaukee 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 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 January is currently the most expensive (average of $263). 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 6h 55m. The distance between Hilton Head Island and Milwaukee is about 838 mi.

  • 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 January is currently the most expensive (average of $263). 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
Oak Creek
New Berlin
Wauwatosa

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