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

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

How long does it take to fly to Hilton Head Island?

On average, it takes 3h 58m to fly from Wisconsin to Hilton Head Island if you fly out of Milwaukee (the most popular airport in Wisconsin) and into Charleston (the most popular airport in Hilton Head Island). If you’re flying out of Appleton and into Charleston, then the flight time is around 4h 29m.

How many flights depart from Wisconsin to Hilton Head Island on average per week?

The number of flights available between Wisconsin and Hilton Head Island is 12 per week as of September 2026. The most frequent departure day is Mon, with 17% of weekly flights leaving on this day.

What airlines fly to Hilton Head Island?

Allegiant Air, American Airlines and United Airlines 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 33% 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.

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?

As of September 2026, there are 3 operators available to choose from 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.

$230 Cheap Flights from Wisconsin to Hilton Head Island in 2026

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Wisconsin to Hilton Head Island

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

11:17 am - 5:52 pmMKE Milwaukee-Mitchell-HHH Hilton Head Island

5h 35m1 stop Charlotte Douglas

6:22 pm - 11:55 pmHHH Hilton Head Island-MKE Milwaukee-Mitchell

6h 33m1 stop Charlotte Douglas

$271American Airlines

Wed, Mar 3 - Wed, Mar 10

7:18 am - 2:10 pmMKE Milwaukee-Mitchell-HHH Hilton Head Island

5h 52m1 stop Chicago O'Hare Intl

2:51 pm - 7:09 pmHHH Hilton Head Island-MKE Milwaukee-Mitchell

5h 18m1 stop Chicago O'Hare Intl

$290United Airlines

Sat, Oct 17 - Sat, Oct 24

10:35 am - 2:10 pmORD Chicago O'Hare Intl-HHH Hilton Head Island

2h 35mnonstop

2:51 pm - 5:05 pmHHH Hilton Head Island-ORD Chicago O'Hare Intl

3h 14mnonstop

$299United Airlines

Sat, Oct 17 - Sat, Oct 24

10:35 am - 2:10 pmORD Chicago O'Hare Intl-HHH Hilton Head Island

2h 35mnonstop

2:51 pm - 5:05 pmHHH Hilton Head Island-ORD Chicago O'Hare Intl

3h 14mnonstop

$299United Airlines

Sat, Oct 17 - Sat, Oct 24

10:02 am - 1:24 pmORD Chicago O'Hare Intl-HHH Hilton Head Island

2h 22mnonstop

12:25 pm - 4:10 pmHHH Hilton Head Island-ORD Chicago O'Hare Intl

4h 45m1 stop Charlotte Douglas

$309American Airlines

Sat, Nov 7 - Tue, Nov 10

5:00 am - 11:05 amORD Chicago O'Hare Intl-HHH Hilton Head Island

5h 05m1 stop Charlotte Douglas

1:55 pm - 3:37 pmHHH Hilton Head Island-ORD Chicago O'Hare Intl

2h 42mnonstop

$309American Airlines

Sat, Oct 31 - Sat, Nov 7

10:02 am - 1:24 pmORD Chicago O'Hare Intl-HHH Hilton Head Island

2h 22mnonstop

12:25 pm - 4:10 pmHHH Hilton Head Island-ORD Chicago O'Hare Intl

4h 45m1 stop Charlotte Douglas

$309American Airlines

Sat, Dec 5 - Tue, Dec 8

8:05 am - 3:27 pmORD Chicago O'Hare Intl-HHH Hilton Head Island

6h 22m1 stop Atlanta Hartsfield-Jackson

12:17 pm - 6:45 pmHHH Hilton Head Island-ORD Chicago O'Hare Intl

7h 28m1 stop Atlanta Hartsfield-Jackson

$319Delta

Wed, Sep 23 - Wed, Sep 30

8:05 am - 3:30 pmORD Chicago O'Hare Intl-HHH Hilton Head Island

6h 25m1 stop Atlanta Hartsfield-Jackson

12:23 pm - 5:47 pmHHH Hilton Head Island-ORD Chicago O'Hare Intl

6h 24m1 stop Atlanta Hartsfield-Jackson

$319Delta

Fri, Oct 30 - Tue, Nov 3

8:05 am - 3:27 pmORD Chicago O'Hare Intl-HHH Hilton Head Island

6h 22m1 stop Atlanta Hartsfield-Jackson

4:17 pm - 10:18 pmHHH Hilton Head Island-ORD Chicago O'Hare Intl

7h 01m1 stop New York LaGuardia

$319Delta

Wed, Sep 23 - Tue, Sep 29

Cheap last minute flights

Enter your travel dates to find the best prices.

10:25 am - 2:03 pmORD Chicago O'Hare Intl-HHH Hilton Head Island

2h 38mnonstop

2:48 pm - 5:05 pmHHH Hilton Head Island-ORD Chicago O'Hare Intl

3h 17mnonstop

$359United Airlines

Wed, Sep 9 - Wed, Sep 16

10:25 am - 2:03 pmORD Chicago O'Hare Intl-HHH Hilton Head Island

2h 38mnonstop

2:48 pm - 5:05 pmHHH Hilton Head Island-ORD Chicago O'Hare Intl

3h 17mnonstop

$374United Airlines

Mon, Sep 7 - Mon, Sep 14

8:05 am - 1:45 pmORD Chicago O'Hare Intl-HHH Hilton Head Island

4h 40m1 stop Charlotte Douglas

12:50 pm - 5:38 pmHHH Hilton Head Island-ORD Chicago O'Hare Intl

5h 48m1 stop Charlotte Douglas

$379American Airlines

Wed, Sep 9 - Wed, Sep 16

8:05 am - 3:27 pmORD Chicago O'Hare Intl-HHH Hilton Head Island

6h 22m1 stop Atlanta Hartsfield-Jackson

12:17 pm - 7:15 pmHHH Hilton Head Island-ORD Chicago O'Hare Intl

7h 58m2 stops Atlanta Hartsfield-Jackson New York LaGuardia

$384Delta

Wed, Sep 9 - Wed, Sep 16

8:00 am - 2:03 pmMSP Minneapolis St Paul-HHH Hilton Head Island

5h 03m1 stop Chicago O'Hare Intl

2:48 pm - 9:52 pmHHH Hilton Head Island-MSP Minneapolis St Paul

8h 04m1 stop Chicago O'Hare Intl

$385United Airlines

Thu, Sep 10 - Mon, Sep 14

8:00 am - 2:03 pmMSP Minneapolis St Paul-HHH Hilton Head Island

5h 03m1 stop Chicago O'Hare Intl

2:48 pm - 9:52 pmHHH Hilton Head Island-MSP Minneapolis St Paul

8h 04m1 stop Chicago O'Hare Intl

$385United Airlines

Thu, Sep 10 - Sun, Sep 13

7:05 am - 3:27 pmORD Chicago O'Hare Intl-HHH Hilton Head Island

7h 22m2 stops Detroit Metropolitan Wayne County Atlanta Hartsfield-Jackson

12:17 pm - 7:15 pmHHH Hilton Head Island-ORD Chicago O'Hare Intl

7h 58m2 stops Atlanta Hartsfield-Jackson New York LaGuardia

$389Delta

Wed, Sep 9 - Wed, Sep 16

7:02 am - 1:17 pmMSP Minneapolis St Paul-HHH Hilton Head Island

5h 15m1 stop Chicago O'Hare Intl

1:40 pm - 5:44 pmHHH Hilton Head Island-MSP Minneapolis St Paul

5h 04m1 stop Chicago O'Hare Intl

$390American Airlines

Tue, Sep 8 - Sat, Sep 19

9:53 am - 1:17 pmORD Chicago O'Hare Intl-HHH Hilton Head Island

2h 24mnonstop

1:40 pm - 3:16 pmHHH Hilton Head Island-ORD Chicago O'Hare Intl

2h 36mnonstop

$409American Airlines

Mon, Sep 7 - Sat, Sep 12

6:00 am - 3:32 pmORD Chicago O'Hare Intl-HHH Hilton Head Island

8h 32m2 stops Minneapolis St Paul Atlanta Hartsfield-Jackson

4:17 pm - 10:18 pmHHH Hilton Head Island-ORD Chicago O'Hare Intl

7h 01m1 stop New York LaGuardia

$459Delta

Mon, Sep 7 - Mon, Sep 14

Cheap direct flights

Enter your travel dates to find the best prices.

10:35 am - 2:10 pmORD Chicago O'Hare Intl-HHH Hilton Head Island

2h 35mnonstop

2:51 pm - 5:05 pmHHH Hilton Head Island-ORD Chicago O'Hare Intl

3h 14mnonstop

$299United Airlines

Sat, Oct 3 - Sat, Oct 10

10:35 am - 2:10 pmORD Chicago O'Hare Intl-HHH Hilton Head Island

2h 35mnonstop

2:51 pm - 5:05 pmHHH Hilton Head Island-ORD Chicago O'Hare Intl

3h 14mnonstop

$299United Airlines

Sat, Oct 3 - Sat, Oct 10

10:35 am - 2:10 pmORD Chicago O'Hare Intl-HHH Hilton Head Island

2h 35mnonstop

2:51 pm - 5:05 pmHHH Hilton Head Island-ORD Chicago O'Hare Intl

3h 14mnonstop

$299United Airlines

Sat, Oct 17 - Sat, Oct 24

10:35 am - 2:10 pmORD Chicago O'Hare Intl-HHH Hilton Head Island

2h 35mnonstop

2:51 pm - 5:05 pmHHH Hilton Head Island-ORD Chicago O'Hare Intl

3h 14mnonstop

$299United Airlines

Sat, Oct 17 - Sat, Oct 24

10:25 am - 2:03 pmORD Chicago O'Hare Intl-HHH Hilton Head Island

2h 38mnonstop

2:48 pm - 5:05 pmHHH Hilton Head Island-ORD Chicago O'Hare Intl

3h 17mnonstop

$374United Airlines

Fri, Sep 18 - Tue, Sep 22

10:25 am - 2:03 pmORD Chicago O'Hare Intl-HHH Hilton Head Island

2h 38mnonstop

2:48 pm - 5:05 pmHHH Hilton Head Island-ORD Chicago O'Hare Intl

3h 17mnonstop

$374United Airlines

Thu, Sep 17 - Mon, Sep 21

10:00 am - 1:25 pmORD Chicago O'Hare Intl-HHH Hilton Head Island

2h 25mnonstop

1:55 pm - 3:37 pmHHH Hilton Head Island-ORD Chicago O'Hare Intl

2h 42mnonstop

$386American Airlines

Sat, Oct 31 - Sat, Nov 7

10:25 am - 2:03 pmORD Chicago O'Hare Intl-HHH Hilton Head Island

2h 38mnonstop

2:48 pm - 5:05 pmHHH Hilton Head Island-ORD Chicago O'Hare Intl

3h 17mnonstop

$399United Airlines

Sat, Sep 19 - Wed, Sep 23

10:00 am - 1:25 pmORD Chicago O'Hare Intl-HHH Hilton Head Island

2h 25mnonstop

1:55 pm - 3:37 pmHHH Hilton Head Island-ORD Chicago O'Hare Intl

2h 42mnonstop

$402American Airlines

Sat, Oct 31 - Sat, Nov 7

10:25 am - 2:03 pmORD Chicago O'Hare Intl-HHH Hilton Head Island

2h 38mnonstop

2:48 pm - 5:05 pmHHH Hilton Head Island-ORD Chicago O'Hare Intl

3h 17mnonstop

$415United Airlines

Thu, Sep 17 - Sun, Sep 20

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United Airlines flights from Wisconsin to Hilton Head Island

Our best United Airlines deals on Wisconsin to Hilton Head Island flight tickets

United Airlines

Oct 17

MKE7:18 amMilwaukee-Mitchell

5h 52m

1 stop

HHH2:10 pmHilton Head Island

Oct 24

HHH2:51 pmHilton Head Island

5h 18m

1 stop

MKE7:09 pmMilwaukee-Mitchell

$290

United Airlines

Oct 17

ORD10:35 amChicago O'Hare Intl

2h 35m

HHH2:10 pmHilton Head Island

Oct 24

HHH2:51 pmHilton Head Island

3h 14m

ORD5:05 pmChicago O'Hare Intl

$299

United Airlines

Oct 20

MSN6:06 amMadison Truax Field

5h 29m

1 stop

HHH12:35 pmHilton Head Island

Oct 24

HHH2:51 pmHilton Head Island

7h 09m

1 stop

MSN9:00 pmMadison Truax Field

$319

Delta flights from Wisconsin to Hilton Head Island

Our best Delta deals on Wisconsin to Hilton Head Island flight tickets

Delta

Sep 23

ORD8:05 amChicago O'Hare Intl

6h 22m

1 stop

HHH3:27 pmHilton Head Island

Sep 30

HHH12:17 pmHilton Head Island

11h 01m

2 stops

ORD10:18 pmChicago O'Hare Intl

$324

Delta

Sep 23

ORD6:00 amChicago O'Hare Intl

8h 27m

2 stops

HHH3:27 pmHilton Head Island

Sep 30

HHH12:17 pmHilton Head Island

9h 14m

2 stops

ORD8:31 pmChicago O'Hare Intl

$329

Delta

Sep 23

ORD6:00 amChicago O'Hare Intl

8h 27m

2 stops

HHH3:27 pmHilton Head Island

Oct 2

HHH4:17 pmHilton Head Island

7h 01m

1 stop

ORD10:18 pmChicago O'Hare Intl

$344

momondo Fare Finder

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 Milwaukee-Mitchell - HHH Hilton Head Island

MKEHHH

Milwaukee-Mitchell

Wed 3/3

11:17 am-5:52 pm

1 stop5h 35m

Hilton Head Island

Wed 3/10

6:22 pm-11:55 pm

1 stop6h 33m

$271

MilwaukeeHilton Head Island

MKE Milwaukee-Mitchell - HHH Hilton Head Island

MKEHHH

Milwaukee-Mitchell

Sat 10/17

7:18 am-2:10 pm

1 stop5h 52m

Hilton Head Island

Sat 10/24

2:51 pm-7:09 pm

1 stop5h 18m

$290

Quickest round-trip

ChicagoHilton Head Island

ORD Chicago O'Hare Intl - HHH Hilton Head Island

ORDHHH

Chicago O'Hare Intl

Sat 10/17

10:35 am-2:10 pm

Nonstop2h 35m

Hilton Head Island

Sat 10/24

2:51 pm-5:05 pm

Nonstop3h 14m

$299

ChicagoHilton Head Island

ORD Chicago O'Hare Intl - HHH Hilton Head Island

ORDHHH

Chicago O'Hare Intl

Sat 10/17

10:35 am-2:10 pm

Nonstop2h 35m

Hilton Head Island

Sat 10/24

2:51 pm-5:05 pm

Nonstop3h 14m

$299

ChicagoHilton Head Island

ORD Chicago O'Hare Intl - HHH Hilton Head Island

ORDHHH

Chicago O'Hare Intl

Sat 11/7

10:02 am-1:24 pm

Nonstop2h 22m

Hilton Head Island

Tue 11/10

12:25 pm-4:10 pm

1 stop4h 45m

$309

ChicagoHilton Head Island

ORD Chicago O'Hare Intl - HHH Hilton Head Island

ORDHHH

Chicago O'Hare Intl

Sat 10/31

5:00 am-11:05 am

1 stop5h 05m

Hilton Head Island

Sat 11/7

1:55 pm-3:37 pm

Nonstop2h 42m

$309

ChicagoHilton Head Island

ORD Chicago O'Hare Intl - HHH Hilton Head Island

ORDHHH

Chicago O'Hare Intl

Sat 12/5

10:02 am-1:24 pm

Nonstop2h 22m

Hilton Head Island

Tue 12/8

12:25 pm-4:10 pm

1 stop4h 45m

$309

ChicagoHilton Head Island

ORD Chicago O'Hare Intl - HHH Hilton Head Island

ORDHHH

Chicago O'Hare Intl

Wed 9/23

8:05 am-3:27 pm

1 stop6h 22m

Hilton Head Island

Wed 9/30

12:17 pm-6:45 pm

1 stop7h 28m

$319

ChicagoHilton Head Island

ORD Chicago O'Hare Intl - HHH Hilton Head Island

ORDHHH

Chicago O'Hare Intl

Fri 10/30

8:05 am-3:30 pm

1 stop6h 25m

Hilton Head Island

Tue 11/3

12:23 pm-5:47 pm

1 stop6h 24m

$319

ChicagoHilton Head Island

ORD Chicago O'Hare Intl - HHH Hilton Head Island

ORDHHH

Chicago O'Hare Intl

Wed 9/23

8:05 am-3:27 pm

1 stop6h 22m

Hilton Head Island

Tue 9/29

4:17 pm-10:18 pm

1 stop7h 01m

$319

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

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

Prices

Airlines

Other information

What is the cheapest month to fly to Hilton Head Island?

If you don’t want to visit Hilton Head Island in June, then you should wait until November to fly from Wisconsin, when ticket prices are also cheap, with an average price of $358.

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

Best Price Found	$230
Fastest flight time	2h 22m
Direct flights	Tue, Thu, Fri and Sun
Airports in Hilton Head Island	1 airport

The best one-way flight to Hilton Head Island from Wisconsin in the past 72 hours is $230. The best round-trip flight deal from Wisconsin to Hilton Head Island found on momondo in the last 72 hours is $271.

The fastest flight from Wisconsin to Hilton Head Island takes 2h 22m

Direct flights go from Wisconsin to Hilton Head Island on Tuesday, Thursday, Friday and Sunday. There are no airlines offering direct flights.

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?
As of September 2026, there are 3 operators available to choose from 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 Airlines	PriceFrom $260	Free Cancellation	Rating 7.1 12,050 reviews		Search American Airlines flights

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.

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Cheap flights from Wisconsin to Hilton Head Island from $230

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 11/5. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

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United Airlines flights from Wisconsin to Hilton Head Island

Our best United Airlines deals on Wisconsin to Hilton Head Island flight tickets

Delta flights from Wisconsin to Hilton Head Island

Our best Delta deals on Wisconsin to Hilton Head Island flight tickets

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

What is the cheapest month to fly to Hilton Head Island?

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

What airlines fly to Hilton Head Island?

How many flights depart from Wisconsin to Hilton Head Island on average per week?

How long does it take to fly to Hilton Head Island?

Cheap Wisconsin to Hilton Head Island flight deals and tips

Best Price Found

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Direct flights

Airports in Hilton Head Island

Frequently asked questions about flying from Wisconsin to Hilton Head Island

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

Traveling to a place near Hilton Head Island?

Why use momondo?

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.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

Find better results for your trip to the United States

Airports servicing South Carolina

Fly your favorite airline to Hilton Head Island

Airlines are sorted and displayed according to clicks in the past 7 days on momondo

Cabin classes currently available on flights to Hilton Head Island

List of cabin classes available on flights landing in Hilton Head Island. Availability may vary depending on flight origin and airline.

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