$369+ Cheap flights from Milwaukee to Hilton Head Island (MKE - HHH)
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 10/17. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — HHH
Nov 3 — Nov 101
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
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
Cheapest
Best
Last-minute
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 October 4, 2026.
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 October 4, 2026.
This American Airlines deal was found by Cheapflights users on 10/3. 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 10/177:45 am -
1 stop4h 35m
Wed 10/2110:55 am -
1 stop6h 45m
Deal found 10/3![American Airlines logo]()
$369
This American Airlines deal was found by Cheapflights users on 10/1. 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 10/1610:54 am -
1 stop5h 44m
Tue 10/202:13 pm -
1 stop7h 14m
Deal found 10/1![American Airlines logo]()
$457
This American Airlines deal was found by Cheapflights users on 9/30. 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 12/225:00 am -
2 stops8h 30m
Sun 12/277:05 pm -
1 stop5h 54m
Deal found 9/30![American Airlines logo]()
$506
This American Airlines deal was found by Cheapflights users on 10/3. 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.
Sun 10/187:00 am -
1 stop6h 26m
Thu 10/222:56 pm -
1 stop6h 31m
Deal found 10/3![American Airlines logo]()
$617
Best flights from Milwaukee to Hilton Head IslandDiscover 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 October 4, 2026.
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 October 4, 2026.
This American Airlines deal was found by Cheapflights users on 10/3. 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 10/177:45 am -
1 stop4h 35m
Wed 10/2110:55 am -
1 stop6h 45m
Deal found 10/3![American Airlines logo]()
$369
This American Airlines deal was found by Cheapflights users on 10/1. 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 10/166:10 am -
2 stops10h 28m
Tue 10/202:13 pm -
1 stop7h 14m
Deal found 10/1![American Airlines logo]()
$462
This American Airlines deal was found by Cheapflights users on 9/30. 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 12/225:00 am -
2 stops8h 30m
Sun 12/277:05 pm -
1 stop5h 54m
Deal found 9/30![American Airlines logo]()
$506
This American Airlines deal was found by Cheapflights users on 10/3. 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.
Sun 10/186:10 am -
2 stops7h 16m
Thu 10/222:56 pm -
1 stop6h 31m
Deal found 10/3![American Airlines logo]()
$622
This American Airlines deal was found by Cheapflights users on 9/30. 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.
Sun 10/117:00 am -
1 stop6h 26m
Fri 10/166:08 pm -
1 stop6h 49m
Deal found 9/30![American Airlines logo]()
$742
Last-minute flights from Milwaukee to Hilton Head IslandDiscover last-minute flight deals from Milwaukee to Hilton Head Island. Data last updated October 4, 2026 and is based on user searches.
Discover last-minute flight deals from Milwaukee to Hilton Head Island. Data last updated October 4, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 9/30. 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.
Sun 10/117:00 am -
1 stop6h 26m
Fri 10/166:08 pm -
1 stop6h 49m
Deal found 9/30![American Airlines logo]()
$742
This American Airlines deal was found by Cheapflights users on 10/1. 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 10/1610:54 am -
1 stop5h 44m
Tue 10/202:13 pm -
1 stop7h 14m
Deal found 10/1![American Airlines logo]()
$457
This American Airlines deal was found by Cheapflights users on 10/3. 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 10/177:45 am -
1 stop4h 35m
Wed 10/2110:55 am -
1 stop6h 45m
Deal found 10/3![American Airlines logo]()
$369
This American Airlines deal was found by Cheapflights users on 10/3. 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.
Sun 10/187:00 am -
1 stop6h 26m
Thu 10/222:56 pm -
1 stop6h 31m
Deal found 10/3![American Airlines logo]()
$617
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 October 4, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $315 (American Airlines) |
One-way from | $220 (Delta) |
Popular in | August |
Cheapest in | September |
Average price | $497 |
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 7,457,451 searches. Data last updated October 4, 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
Cheapest round-trip
Quickest round-trip
MilwaukeeHilton Head Island
MKE Milwaukee-Mitchell - HHH Hilton Head Island
MKEHHH
Milwaukee-Mitchell
Sat 10/17
7:45 am-1:20 pm
1 stop4h 35m
Hilton Head Island
Wed 10/21
10:55 am-4:40 pm
1 stop6h 45m
$369
MilwaukeeHilton Head Island
MKE Milwaukee-Mitchell - HHH Hilton Head Island
MKEHHH
Milwaukee-Mitchell
Fri 10/16
6:10 am-5:38 pm
2 stops10h 28m
Hilton Head Island
Tue 10/20
2:13 pm-8:27 pm
1 stop7h 14m
$462
MilwaukeeHilton Head Island
MKE Milwaukee-Mitchell - HHH Hilton Head Island
MKEHHH
Milwaukee-Mitchell
Tue 12/22
5:00 am-2:30 pm
2 stops8h 30m
Hilton Head Island
Sun 12/27
7:05 pm-11:59 pm
1 stop5h 54m
$506
MilwaukeeHilton Head Island
MKE Milwaukee-Mitchell - HHH Hilton Head Island
MKEHHH
Milwaukee-Mitchell
Sun 10/18
6:10 am-2:26 pm
2 stops7h 16m
Hilton Head Island
Thu 10/22
2:56 pm-8:27 pm
1 stop6h 31m
$622
MilwaukeeHilton Head Island
MKE Milwaukee-Mitchell - HHH Hilton Head Island
MKEHHH
Milwaukee-Mitchell
Sun 10/11
7:00 am-2:26 pm
1 stop6h 26m
Hilton Head Island
Fri 10/16
6:08 pm-11:57 pm
1 stop6h 49m
$742
Sorted by cheapest first
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 October.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
- 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.
MKE-HHH
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 October 4, 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.
Crew
7.9
Boarding
7.4
Overall
7.0
Comfort
7.2
Food
6.4
Entertainment
6.8
Reviews
1 / 20
10.0
ExcellentLinda,Jul 2026
ROA - CLT
Crew
7.9
Boarding
7.4
Overall
7.0
Comfort
7.2
Food
6.4
Entertainment
6.8
Reviews
1 / 20
10.0
ExcellentLinda,Jul 2026
ROA - CLT
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.
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
Complete your trip
Flights by cabin class
Hilton Head Island flight routes
Other flight options
Other flights from Milwaukee
Popular flights
Alternative routes for Milwaukee to Hilton Head Island
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Hilton Head Island by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Milwaukee to Hilton Head Island by cabin class
Find flights from Milwaukee to Hilton Head Island, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Other flights to Hilton Head Island
Explore flights to Hilton Head Island departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on October 4, 2026.
Milwaukee and Hilton Head Island flights
Browse other Milwaukee and Hilton Head Island flight options. Last updated on October 4, 2026.
Other flights from Milwaukee
Browse through other flights departing from Milwaukee. Flights are based on user searches made on Cheapflights and were last updated on October 4, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
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 7,457,451 searches. Data last updated October 4, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$260 | Average$364 | FlexibilityNo cancel fee | On-time71% |