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$214+ Cheap flights from Hilton Head Island (HHH) to Wisconsin

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 12/8. Fares are subject to change and may not be available on all flights or dates of travel.
HHH — MKE
Dec 13 — Dec 201
Sat 12/13
Sat 12/20
1 adult, Economy
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Find flight deals from Hilton Head Island to Wisconsin

Cheapest flights from Hilton Head Island to Wisconsin
Explore the most affordable flight options available from Hilton Head Island to Wisconsin. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 13, 2025.

This American Airlines deal was found by Cheapflights users on 11/10. 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.
Mon 11/241:02 pmHHH - ORD
1 stop5h 50mAmerican Airlines
Fri 11/2810:29 amORD - HHH
1 stop6h 40mAmerican Airlines
Deal found 11/10$367
This American Airlines deal was found by Cheapflights users on 11/12. 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.
Mon 11/177:07 pmHHH - ORD
1 stop5h 30mAmerican Airlines
Sat 11/226:06 amORD - HHH
1 stop5h 00mAmerican Airlines
Deal found 11/12$397
This American Airlines deal was found by Cheapflights users on 11/11. 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.
Tue 11/181:02 pmHHH - ORD
2 stops9h 21mAmerican Airlines
Mon 11/246:06 amORD - HHH
2 stops7h 51mAmerican Airlines
Deal found 11/11$407
This American Airlines deal was found by Cheapflights users on 11/11. 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 11/177:07 pmHHH - ORD
1 stop5h 30mAmerican Airlines
Mon 11/246:46 amORD - HHH
1 stop7h 11mAmerican Airlines
Deal found 11/11$425
This American Airlines deal was found by Cheapflights users on 11/12. 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.
Thu 11/2710:54 amHHH - ORD
2 stops22h 52mAmerican Airlines
Mon 12/16:06 amORD - HHH
2 stops7h 13mAmerican Airlines
Deal found 11/12$491
This American Airlines deal was found by Cheapflights users on 11/12. 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.
Thu 12/182:46 pmHHH - ORD
1 stop5h 36mAmerican Airlines
Sun 12/215:00 amORD - HHH
1 stop4h 44mAmerican Airlines
Deal found 11/12$633

Cheap flight deals from Hilton Head Island to Wisconsin

Keep the following information in mind while searching for Hilton Head Island to Wisconsin flight deals. Data was last updated November 13, 2025.

Round-trip from

$334
(United Airlines)

One-way from

$214
(American Airlines)
From Hilton Head Island to Wisconsin
Search Deals
One-way flight from Hilton Head Island to Wisconsin
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Hilton Head Island to Wisconsin 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 November 13, 2025.
Use the filters below to find and compare flights from Hilton Head Island to Wisconsin that are best for you.

Fly from

Hilton Head Island

Fly to

Wisconsin

Route

Depart

Return

Price

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Thu 4/2

3:00 pm-4:45 pm

Nonstop2h 45m

Chicago O'Hare Intl

Tue 4/7

10:35 am-1:52 pm

Nonstop2h 17m

$334

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Thu 4/2

3:00 pm-4:45 pm

Nonstop2h 45m

Chicago O'Hare Intl

Wed 4/8

10:35 am-1:52 pm

Nonstop2h 17m

$334

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Thu 4/2

3:00 pm-4:45 pm

Nonstop2h 45m

Chicago O'Hare Intl

Sun 4/12

10:35 am-1:52 pm

Nonstop2h 17m

$334

Hilton Head IslandMilwaukee

HHH - MKE

HHHMKE

Hilton Head Island

Sat 2/21

11:03 am-3:57 pm

2 stops5h 54m

Milwaukee-Mitchell

Sat 2/28

7:00 am-2:28 pm

1 stop6h 28m

$341

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Mon 11/24

1:02 pm-9:05 pm

2 stops9h 03m

Chicago O'Hare Intl

Fri 11/28

10:29 am-6:09 pm

1 stop6h 40m

$372

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Wed 12/3

12:52 pm-6:02 pm

1 stop6h 10m

Chicago O'Hare Intl

Sun 12/7

5:00 am-11:51 am

1 stop5h 51m

$397

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Tue 3/31

3:00 pm-4:45 pm

Nonstop2h 45m

Chicago O'Hare Intl

Sun 4/12

10:35 am-1:52 pm

Nonstop2h 17m

$398

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Tue 3/31

3:00 pm-4:45 pm

Nonstop2h 45m

Chicago O'Hare Intl

Wed 4/8

10:35 am-1:52 pm

Nonstop2h 17m

$398

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Wed 4/1

3:00 pm-4:45 pm

Nonstop2h 45m

Chicago O'Hare Intl

Wed 4/8

10:35 am-1:52 pm

Nonstop2h 17m

$398

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Tue 3/31

3:00 pm-4:45 pm

Nonstop2h 45m

Chicago O'Hare Intl

Tue 4/7

10:35 am-1:52 pm

Nonstop2h 17m

$398

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/12

Showing 1-10 of 23 results
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Best time to book a flight from Hilton Head Island to Wisconsin

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

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

Currently, August is the cheapest month in which you can book a flight from Hilton Head Island to Wisconsin (average of $78). Flying from Hilton Head Island to Wisconsin in January is currently the most expensive (average of $263). 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.

Related info for your journey

Find useful and relevant information for your journey from Hilton Head Island to Wisconsin. 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 from for flights from Hilton Head Island to Wisconsin?

    Hilton Head Island (HHH), located 3.3 mi from the city center, is the airport you fly out of when you book flights from Hilton Head Island to Wisconsin.

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

    There are many flights that can get you from Hilton Head Island to Wisconsin in 2h 45m. Fly via United Airlines or American Airlines to get the fastest option. Hilton Head Island and Wisconsin are separated by a distance of 781 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

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

    When deciding which route to take from Hilton Head Island to Wisconsin consider Hilton Head Island - Milwaukee-Mitchell, Hilton Head Island - Chicago O'Hare Intl or Hilton Head Island - Minneapolis St Paul as they are the most popular.

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

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

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

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Hilton Head Island to Wisconsin.

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

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

    Currently, August is the cheapest month in which you can book a flight from Hilton Head Island to Wisconsin (average of $78). Flying from Hilton Head Island to Wisconsin in January is currently the most expensive (average of $263). 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

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