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Hilton Head Island

$174+ Cheap flights from Wisconsin to Hilton Head Island (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 9/10. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — HHH
Jul 15 — Jul 221
Wed 7/15
Wed 7/22
1 adult, Economy
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Cheap flight deals from Wisconsin to Hilton Head Island

Cheapest flights from Wisconsin to Hilton Head Island
Explore the most affordable flight options available from Wisconsin to Hilton Head Island. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 15, 2026.

This American Airlines deal was found by Cheapflights users on 6/10. 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 7/215:02 am
MKE
-
HHH
1 stop7h 31m
American Airlines
Tue 7/284:55 pm
HHH
-
MKE
1 stop5h 59m
American Airlines
Deal found 6/10$261
This Delta deal was found by Cheapflights users on 6/10. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/216:00 am
MKE
-
HHH
2 stops8h 29m
Delta
Tue 7/2812:11 pm
HHH
-
MKE
1 stop5h 20m
Delta
Deal found 6/10$266
This American Airlines deal was found by Cheapflights users on 6/11. 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 7/1510:00 am
ORD
-
HHH
Nonstop2h 33m
American Airlines
Wed 7/222:03 pm
HHH
-
ORD
Nonstop2h 36m
American Airlines
Deal found 6/11$269
This American Airlines deal was found by Cheapflights users on 6/11. 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 7/206:30 am
ORD
-
HHH
1 stop6h 46m
American Airlines
Mon 7/272:03 pm
HHH
-
ORD
Nonstop2h 36m
American Airlines
Deal found 6/11$279
This Delta deal was found by Cheapflights users on 6/13. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/2610:03 am
MKE
-
HHH
1 stop4h 24m
Delta
Tue 10/64:00 pm
HHH
-
MKE
1 stop5h 56m
Delta
Deal found 6/13$285
This American Airlines deal was found by Cheapflights users on 6/10. 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 7/109:00 am
ORD
-
HHH
1 stop6h 25m
American Airlines
Fri 7/1711:47 am
HHH
-
ORD
1 stop6h 52m
American Airlines
Deal found 6/10$289
This American Airlines deal was found by Cheapflights users on 6/12. 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 7/146:10 am
MSP
-
HHH
1 stop6h 23m
American Airlines
Tue 7/214:55 pm
HHH
-
MSP
1 stop7h 27m
American Airlines
Deal found 6/12$291
This Delta deal was found by Cheapflights users on 6/9. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/116:00 am
ORD
-
HHH
2 stops8h 32m
Delta
Tue 8/1812:15 pm
HHH
-
ORD
1 stop5h 36m
Delta
Deal found 6/9$294
This American Airlines deal was found by Cheapflights users on 6/14. 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 7/910:00 am
ORD
-
HHH
Nonstop2h 33m
American Airlines
Wed 7/1511:07 am
HHH
-
ORD
1 stop7h 17m
American Airlines
Deal found 6/14$299
This American Airlines deal was found by Cheapflights users on 6/13. 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 9/268:03 am
MKE
-
HHH
1 stop4h 42m
American Airlines
Tue 10/66:13 pm
HHH
-
MKE
1 stop6h 58m
American Airlines
Deal found 6/13$304
This United Airlines deal was found by Cheapflights users on 6/13. 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.
Thu 8/206:30 am
MSN
-
HHH
1 stop6h 33m
United Airlines
Thu 8/272:48 pm
HHH
-
MSN
1 stop7h 05m
United Airlines
Deal found 6/13$309
This American Airlines deal was found by Cheapflights users on 6/10. 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 6/266:29 am
ORD
-
HHH
1 stop6h 44m
American Airlines
Tue 7/74:55 pm
HHH
-
ORD
1 stop6h 05m
American Airlines
Deal found 6/10$309

Find flight deals from Wisconsin to Hilton Head Island

Keep the following information in mind while searching for Wisconsin to Hilton Head Island flight deals. Data was last updated June 15, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$261
(American Airlines)

One-way from

$174
(United Airlines)

Popular in

July

Cheapest in

January

Average price

$328
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 Wisconsin to Hilton Head Island
Search Deals
One-way flight from Wisconsin to Hilton Head Island
Search Deals
Highest demand for flights based on searches. 9% potential increase in price ($36 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 June 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Wisconsin 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 June 15, 2026.
Use the filters below to find and compare flights from Wisconsin 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

6:00 am-3:29 pm

2 stops8h 29m

Hilton Head Island

Tue 7/28

4:14 pm-10:30 pm

1 stop7h 16m

$266

MilwaukeeHilton Head Island

MKE - HHH

MKEHHH

Milwaukee-Mitchell

Sat 9/26

10:03 am-3:27 pm

1 stop4h 24m

Hilton Head Island

Tue 10/6

4:00 pm-8:56 pm

1 stop5h 56m

$285

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Tue 8/11

6:00 am-3:32 pm

2 stops8h 32m

Hilton Head Island

Tue 8/18

12:15 pm-10:24 pm

2 stops11h 09m

$300

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Sat 8/8

10:45 am-2:21 pm

Nonstop2h 36m

Hilton Head Island

Tue 8/11

2:48 pm-5:05 pm

Nonstop3h 17m

$324

MilwaukeeHilton Head Island

MKE - HHH

MKEHHH

Milwaukee-Mitchell

Fri 9/18

10:11 am-3:27 pm

1 stop4h 16m

Hilton Head Island

Mon 9/28

12:15 pm-5:33 pm

1 stop6h 18m

$330

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Thu 8/13

10:25 am-2:03 pm

Nonstop2h 38m

Hilton Head Island

Mon 8/17

2:48 pm-5:05 pm

Nonstop3h 17m

$349

MinneapolisHilton Head Island

MSP - HHH

MSPHHH

Minneapolis St Paul

Sat 7/18

6:10 am-1:21 pm

1 stop6h 11m

Hilton Head Island

Thu 7/23

4:55 pm-11:22 pm

1 stop7h 27m

$355

AppletonHilton Head Island

ATW - HHH

ATWHHH

Appleton Intl

Wed 7/29

5:00 am-1:33 pm

1 stop7h 33m

Hilton Head Island

Wed 8/5

10:57 am-5:22 pm

2 stops7h 25m

$362

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Sat 7/25

5:07 am-11:05 am

1 stop4h 58m

Hilton Head Island

Fri 7/31

11:47 am-4:46 pm

1 stop5h 59m

$379

MilwaukeeHilton Head Island

MKE - HHH

MKEHHH

Milwaukee-Mitchell

Wed 8/12

10:22 am-3:32 pm

1 stop4h 10m

Hilton Head Island

Sun 8/16

12:15 pm-4:14 pm

1 stop4h 59m

$393

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/12

Showing 1-10 of 57 resultsSorted by cheapest first
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Best time to book a flight from Wisconsin to Hilton Head Island

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

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

Currently, June is the cheapest month in which you can book a flight from Wisconsin to Hilton Head Island (average of $95). Flying from Wisconsin to Hilton Head Island in March is currently the most expensive (average of $338). 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.

How much does it cost to fly round-trip from Wisconsin to Hilton Head Island?

Related info for your journey

Find useful and relevant information for your journey from Wisconsin 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 airport do you fly into for flights to Hilton Head Island from Wisconsin?

    For a flight from Wisconsin to Hilton Head Island, you will be flying into Hilton Head. Hilton Head Island (HHH) is just 3.3 mi from the center of the city.

  • How long is the flight from Wisconsin to Hilton Head Island?

    Airlines like Delta, United Airlines, and American Airlines fly from Wisconsin to Hilton Head Island in about 2h 36m. The time it takes to get you to your destination can typically vary by up to 11h 37m. Airlines will cover a distance of 781 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the most popular routes from Wisconsin to Hilton Head Island?

    While some choose either Milwaukee-Mitchell - Hilton Head Island or Minneapolis St Paul - Hilton Head Island, Chicago O'Hare Intl - Hilton Head Island is the most popular route from Wisconsin to Hilton Head Island.

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

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

  • How can I find direct flights from Wisconsin 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 Wisconsin to Hilton Head Island.

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

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

    Currently, June is the cheapest month in which you can book a flight from Wisconsin to Hilton Head Island (average of $95). Flying from Wisconsin to Hilton Head Island in March is currently the most expensive (average of $338). 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 Hilton Head Island?

Book flights to Hilton Head Island if you plan to visit one of these locations
Beaufort

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Alternative routes for Wisconsin to Hilton Head Island

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Top 2 airlines flying from Wisconsin to Hilton Head Island

Discover the top 2 airlines that operate flights from Wisconsin 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 June 15, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$248Average$452FlexibilityNo cancel feeOn-time71%
DeltaCheapest$260Average$345FlexibilityNo cancel feeOn-timeN/A

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