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Cheap flights from Wisconsin to Hilton Head Island from $99

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Wisconsin to Hilton Head Island departing on 4/27. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

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Find the cheapest flights from Wisconsin to Hilton Head Island

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
8:10 am - 3:22 pm
ORD
-
HHH
6h 12m
1 stop
Delta Logo
4:00 pm - 10:43 pm
HHH
-
ORD
7h 43m
1 stop
$147Delta
Tue, Jun 2 - Tue, Jun 9
American Airlines Logo
5:00 am - 10:33 am
ORD
-
HHH
4h 33m
1 stop
American Airlines Logo
6:20 pm - 12:06 am
HHH
-
ORD
6h 46m
1 stop
$205American Airlines
Thu, Feb 19 - Mon, Feb 23
Delta Logo
8:10 am - 3:22 pm
ORD
-
HHH
6h 12m
1 stop
Delta Logo
4:00 pm - 10:43 pm
HHH
-
ORD
7h 43m
1 stop
$208Delta
Wed, Jun 3 - Tue, Jun 9
American Airlines Logo
9:40 am - 5:44 pm
ORD
-
HHH
7h 04m
2 stops
American Airlines Logo
6:20 pm - 12:06 am
HHH
-
ORD
6h 46m
1 stop
$210American Airlines
Thu, Feb 19 - Mon, Feb 23
Delta Logo
8:10 am - 3:22 pm
ORD
-
HHH
6h 12m
1 stop
Delta Logo
4:05 pm - 10:36 pm
HHH
-
ORD
7h 31m
1 stop
$233Delta
Tue, May 26 - Tue, Jun 2
Delta Logo
8:10 am - 3:22 pm
ORD
-
HHH
6h 12m
1 stop
Delta Logo
4:00 pm - 10:43 pm
HHH
-
ORD
7h 43m
1 stop
$254Delta
Sun, May 31 - Tue, Jun 9
Delta Logo
8:10 am - 3:22 pm
ORD
-
HHH
6h 12m
1 stop
Delta Logo
4:00 pm - 5:48 pm
HHH
-
ORD
26h 48m
1 stop
$255Delta
Tue, Jun 2 - Mon, Jun 8
American Airlines Logo
5:00 am - 10:33 am
ORD
-
HHH
4h 33m
1 stop
American Airlines Logo
4:11 pm - 9:24 pm
HHH
-
ORD
6h 13m
1 stop
$267American Airlines
Mon, Mar 9 - Wed, Mar 11
American Airlines Logo
10:54 am - 4:44 pm
MSN
-
HHH
4h 50m
1 stop
American Airlines Logo
4:11 pm - 10:00 pm
HHH
-
MSN
6h 49m
1 stop
$269American Airlines
Tue, Mar 10 - Tue, Mar 17
United Airlines Logo
8:00 am - 2:06 pm
GRB
-
HHH
5h 06m
1 stop
United Airlines Logo
3:00 pm - 7:13 pm
HHH
-
GRB
5h 13m
1 stop
$874United Airlines
Fri, Apr 10 - Sun, Apr 12

United Airlines flights from Wisconsin to Hilton Head Island

Our best United Airlines deals on Wisconsin to Hilton Head Island flight tickets
United Airlines
May 18
ORD10:45 amChicago O'Hare Intl
2h 26m
HHH2:11 pmHilton Head Island
May 23
HHH3:00 pmHilton Head Island
2h 45m
ORD4:45 pmChicago O'Hare Intl
$283
United Airlines
May 12
ORD10:45 amChicago O'Hare Intl
2h 26m
HHH2:11 pmHilton Head Island
May 16
HHH3:08 pmHilton Head Island
2h 41m
ORD4:49 pmChicago O'Hare Intl
$284
United Airlines
Apr 24
ORD10:40 amChicago O'Hare Intl
2h 26m
HHH2:06 pmHilton Head Island
Apr 28
HHH3:00 pmHilton Head Island
2h 44m
ORD4:44 pmChicago O'Hare Intl
$339

American Airlines flights from Wisconsin to Hilton Head Island

Our best American Airlines deals on Wisconsin to Hilton Head Island flight tickets
American Airlines
Feb 19
ORD5:00 amChicago O'Hare Intl
4h 33m
1 stop
HHH10:33 amHilton Head Island
Feb 23
HHH6:20 pmHilton Head Island
6h 46m
1 stop
ORD12:06 amChicago O'Hare Intl
$205
American Airlines
Feb 19
ORD9:40 amChicago O'Hare Intl
7h 04m
2 stops
HHH5:44 pmHilton Head Island
Feb 23
HHH6:20 pmHilton Head Island
6h 46m
1 stop
ORD12:06 amChicago O'Hare Intl
$210
American Airlines
Mar 9
ORD5:00 amChicago O'Hare Intl
4h 33m
1 stop
HHH10:33 amHilton Head Island
Mar 11
HHH4:11 pmHilton Head Island
6h 13m
1 stop
ORD9:24 pmChicago O'Hare Intl
$267

momondo 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, momondo users made 832,500 searches. Data last updated February 7, 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

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Tue 6/2

8:10 am-3:22 pm

1 stop6h 12m

Hilton Head Island

Tue 6/9

4:00 pm-10:43 pm

1 stop7h 43m

$147

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Thu 2/19

5:00 am-10:33 am

1 stop4h 33m

Hilton Head Island

Mon 2/23

6:20 pm-12:06 am

1 stop6h 46m

$205

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Wed 6/3

8:10 am-3:22 pm

1 stop6h 12m

Hilton Head Island

Tue 6/9

4:00 pm-10:43 pm

1 stop7h 43m

$208

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Thu 2/19

9:40 am-5:44 pm

2 stops7h 04m

Hilton Head Island

Mon 2/23

6:20 pm-12:06 am

1 stop6h 46m

$210

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Tue 5/26

8:10 am-3:22 pm

1 stop6h 12m

Hilton Head Island

Tue 6/2

4:05 pm-10:36 pm

1 stop7h 31m

$233

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Sun 5/31

8:10 am-3:22 pm

1 stop6h 12m

Hilton Head Island

Tue 6/9

4:00 pm-10:43 pm

1 stop7h 43m

$254

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Tue 6/2

8:10 am-3:22 pm

1 stop6h 12m

Hilton Head Island

Mon 6/8

4:00 pm-5:48 pm

1 stop26h 48m

$255

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Mon 3/9

5:00 am-10:33 am

1 stop4h 33m

Hilton Head Island

Wed 3/11

4:11 pm-9:24 pm

1 stop6h 13m

$267

MadisonHilton Head Island

MSN - HHH

MSNHHH

Madison Truax Field

Tue 3/10

10:54 am-4:44 pm

1 stop4h 50m

Hilton Head Island

Tue 3/17

4:11 pm-10:00 pm

1 stop6h 49m

$269

Green BayHilton Head Island

GRB - HHH

GRBHHH

Green Bay Austin-Straubel

Fri 4/10

8:00 am-2:06 pm

1 stop5h 06m

Hilton Head Island

Sun 4/12

3:00 pm-7:13 pm

1 stop5h 13m

$874

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Hilton Head Island from

How to get the cheapest flight ticket from Wisconsin to Hilton Head Island

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest airline that flies from Wisconsin to Hilton Head Island?

Delta, American Airlines, and United Airlines are the most popular carriers operating from Wisconsin to Hilton Head Island

What airlines fly to Hilton Head Island?

Allegiant Air, American Airlines and Delta are the top three most popular airlines that fly to Hilton Head Island from Wisconsin according to our data. Allegiant Air is the first choice among our users, with 38% of people opting to fly with this airline when traveling to Hilton Head Island. Keep in mind that there are 5 different airlines that fly to Hilton Head Island on a routine basis, so you have a few additional options to choose from.

Cheap Wisconsin to Hilton Head Island flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Wisconsin to Hilton Head Island

Fastest flight time

2h 24m

Direct flights

Every day

Airports in Hilton Head Island

1 airport
The fastest flight from Wisconsin to Hilton Head Island takes 2h 24m
Direct flights go from Wisconsin to Hilton Head Island every day.
There is 1 airport in Hilton Head Island. From Wisconsin there are direct flights to Hilton Head Island (HHH).
Search flight deals

  • When did momondo last update prices for flights from Wisconsin to Hilton Head Island Airport?

    Prices for flights from Wisconsin to Hilton Head Island Airport are refreshed on a daily basis.

  • How many operators does momondo search for flights from Wisconsin to Hilton Head Island Airport?

  • How old do you have to be to fly from Wisconsin to Hilton Head Island Airport?

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Wisconsin to Hilton Head Island Airport.

  • What documentation or ID do you need to fly to Hilton Head Island Airport?

    The travel and health documents required for your trip to Hilton Head Island Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Hilton Head Island Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

Best airlines flying from Wisconsin to Hilton Head Island

Compare and see reviews for airlines that fly from Wisconsin to Hilton Head Island with momondo
Airline
Rating
Free Cancellation
Price
DeltaPriceFrom $223Free CancellationRating
7.9
8,162 reviews
Search Delta flights
American AirlinesPriceFrom $233Free CancellationRating
7.2
11,248 reviews
Search American Airlines flights

Traveling to a place near Hilton Head Island?

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

Why use momondo?

Why should I use momondo to find a flight deal from Wisconsin to Hilton Head Island?

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Wisconsin to Hilton Head Island for you.

Can I find flights from Wisconsin to Hilton Head Island with flexible booking policies on momondo?

All flight searches from Wisconsin to Hilton Head Island on momondo can be filtered to show those which offer flexible booking policies.

How can momondo help me find flights from Wisconsin to Hilton Head Island?

Once you have performed a search for Wisconsin to Hilton Head Island flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

I’m not ready to book a flight from Wisconsin to Hilton Head Island right now. Can momondo alert me if prices change?

Of course. momondo tracks the price of Wisconsin to Hilton Head Island flights. All you need is a valid email address and we will do the rest; it is that quick and easy.

An easier way to manage your Hilton Head Island trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
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