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Cheap flights from Wisconsin to Hilton Head Island from $173

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 5/18. 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.
United Airlines Logo
10:45 am - 2:21 pm
ORD
-
HHH
2h 36mnonstop
United Airlines Logo
3:05 pm - 4:51 pm
HHH
-
ORD
2h 46mnonstop
$269United Airlines
Wed, Jul 1 - Wed, Jul 8
Delta Logo
7:07 am - 3:33 pm
ORD
-
HHH
7h 26m
1 stop
Delta Logo
4:16 pm - 10:36 pm
HHH
-
ORD
7h 20m
1 stop
$289Delta
Tue, May 26 - Tue, Jun 2
American Airlines Logo
8:12 am - 1:39 pm
MKE
-
HHH
4h 27m
1 stop
American Airlines Logo
2:43 pm - 12:02 am
HHH
-
MKE
10h 19m
2 stops
$290American Airlines
Tue, Jun 2 - Tue, Jun 9
Delta Logo
6:24 am - 3:33 pm
ORD
-
HHH
8h 09m
2 stops
Delta Logo
12:13 pm - 5:04 pm
HHH
-
ORD
5h 51m
1 stop
$294Delta
Tue, Jun 2 - Tue, Jun 9
American Airlines Logo
5:00 am - 2:13 pm
MKE
-
HHH
8h 13m
2 stops
American Airlines Logo
2:43 pm - 11:10 pm
HHH
-
MKE
9h 27m
2 stops
$296American Airlines
Tue, Jun 2 - Tue, Jun 9
Delta Logo
10:13 am - 3:33 pm
MKE
-
HHH
4h 20m
1 stop
Delta Logo
12:13 pm - 4:32 pm
HHH
-
MKE
5h 19m
1 stop
$297Delta
Tue, Jun 2 - Tue, Jun 9
Delta Logo
8:08 am - 3:32 pm
ORD
-
HHH
6h 24m
1 stop
Delta Logo
4:15 pm - 10:48 pm
HHH
-
ORD
7h 33m
1 stop
$299Delta
Tue, Jun 23 - Mon, Jun 29
Delta Logo
6:24 am - 3:33 pm
ORD
-
HHH
8h 09m
2 stops
Delta Logo
12:13 pm - 10:34 pm
HHH
-
ORD
11h 21m
2 stops
$300Delta
Tue, Jun 2 - Tue, Jun 9
American Airlines Logo
5:00 am - 1:33 pm
MKE
-
HHH
7h 33m
1 stop
American Airlines Logo
2:09 pm - 6:15 pm
HHH
-
MKE
5h 06m
1 stop
$309American Airlines
Tue, May 26 - Wed, Jun 3
Delta Logo
7:07 am - 3:33 pm
ORD
-
HHH
7h 26m
1 stop
Delta Logo
4:16 pm - 10:36 pm
HHH
-
ORD
7h 20m
1 stop
$309Delta
Tue, May 26 - Tue, Jun 2

United Airlines flights from Wisconsin to Hilton Head Island

Our best United Airlines deals on Wisconsin to Hilton Head Island flight tickets
United Airlines
Jul 1
ORD10:45 amChicago O'Hare Intl
2h 36m
HHH2:21 pmHilton Head Island
Jul 8
HHH3:05 pmHilton Head Island
2h 46m
ORD4:51 pmChicago O'Hare Intl
$269
United Airlines
Jul 6
ORD10:45 amChicago O'Hare Intl
2h 36m
HHH2:21 pmHilton Head Island
Jul 14
HHH3:05 pmHilton Head Island
2h 46m
ORD4:51 pmChicago O'Hare Intl
$383
United Airlines
Jun 2
ORD10:45 amChicago O'Hare Intl
2h 36m
HHH2:21 pmHilton Head Island
Jun 9
HHH1:45 pmHilton Head Island
8h 15m
1 stop
ORD9:00 pmChicago O'Hare Intl
$387

Delta flights from Wisconsin to Hilton Head Island

Our best Delta deals on Wisconsin to Hilton Head Island flight tickets
Delta
May 26
ORD7:07 amChicago O'Hare Intl
7h 26m
1 stop
HHH3:33 pmHilton Head Island
Jun 2
HHH4:16 pmHilton Head Island
7h 20m
1 stop
ORD10:36 pmChicago O'Hare Intl
$289
Delta
Jun 2
ORD6:24 amChicago O'Hare Intl
8h 09m
2 stops
HHH3:33 pmHilton Head Island
Jun 9
HHH12:13 pmHilton Head Island
5h 51m
1 stop
ORD5:04 pmChicago O'Hare Intl
$294
Delta
Jun 2
MKE10:13 amMilwaukee-Mitchell
4h 20m
1 stop
HHH3:33 pmHilton Head Island
Jun 9
HHH12:13 pmHilton Head Island
5h 19m
1 stop
MKE4:32 pmMilwaukee-Mitchell
$297

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 May 9, 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
Quickest round-trip

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Wed 7/1

10:45 am-2:21 pm

Nonstop2h 36m

Hilton Head Island

Wed 7/8

3:05 pm-4:51 pm

Nonstop2h 46m

$269

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Tue 5/26

7:07 am-3:33 pm

1 stop7h 26m

Hilton Head Island

Tue 6/2

4:16 pm-10:36 pm

1 stop7h 20m

$289

MilwaukeeHilton Head Island

MKE - HHH

MKEHHH

Milwaukee-Mitchell

Tue 6/2

8:12 am-1:39 pm

1 stop4h 27m

Hilton Head Island

Tue 6/9

2:43 pm-12:02 am

2 stops10h 19m

$290

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Tue 6/2

6:24 am-3:33 pm

2 stops8h 09m

Hilton Head Island

Tue 6/9

12:13 pm-5:04 pm

1 stop5h 51m

$294

MilwaukeeHilton Head Island

MKE - HHH

MKEHHH

Milwaukee-Mitchell

Tue 6/2

5:00 am-2:13 pm

2 stops8h 13m

Hilton Head Island

Tue 6/9

2:43 pm-11:10 pm

2 stops9h 27m

$296

MilwaukeeHilton Head Island

MKE - HHH

MKEHHH

Milwaukee-Mitchell

Tue 6/2

10:13 am-3:33 pm

1 stop4h 20m

Hilton Head Island

Tue 6/9

12:13 pm-4:32 pm

1 stop5h 19m

$297

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Tue 6/23

8:08 am-3:32 pm

1 stop6h 24m

Hilton Head Island

Mon 6/29

4:15 pm-10:48 pm

1 stop7h 33m

$299

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Tue 6/2

6:24 am-3:33 pm

2 stops8h 09m

Hilton Head Island

Tue 6/9

12:13 pm-10:34 pm

2 stops11h 21m

$300

MilwaukeeHilton Head Island

MKE - HHH

MKEHHH

Milwaukee-Mitchell

Tue 5/26

5:00 am-1:33 pm

1 stop7h 33m

Hilton Head Island

Wed 6/3

2:09 pm-6:15 pm

1 stop5h 06m

$309

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Tue 5/26

7:07 am-3:33 pm

1 stop7h 26m

Hilton Head Island

Tue 6/2

4:16 pm-10:36 pm

1 stop7h 20m

$309

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 month to fly to Hilton Head Island?

If you don’t want to visit Hilton Head Island in September, then you should wait until December to fly from Wisconsin, when ticket prices are also cheap, with an average price of $248.

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 26m

Direct flights

Every day

Airports in Hilton Head Island

1 airport
The fastest flight from Wisconsin to Hilton Head Island takes 2h 26m
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

Frequently asked questions about flying from Wisconsin to Hilton Head Island

  • 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
American AirlinesPriceFrom $248Free CancellationRating
7.1
11,669 reviews
Search American Airlines flights
DeltaPriceFrom $260Free CancellationRating
7.9
8,457 reviews
Search Delta 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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