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$169+ Cheap flights from Hilton Head Island (HHH) to Wisconsin

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 2/3. Fares are subject to change and may not be available on all flights or dates of travel.
HHH — MKE
Feb 5 — Feb 121
Thu 2/5
Thu 2/12
1 adult, Economy
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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 January 6, 2026.

Round-trip from

$169
(American Airlines)
From Hilton Head Island to Wisconsin
Search Deals

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 January 6, 2026.

This American Airlines deal was found by Cheapflights users on 1/5. 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 2/312:51 pmHHH - ORD
1 stop6h 10mAmerican Airlines
Tue 2/106:05 amORD - HHH
1 stop5h 15mAmerican Airlines
Deal found 1/5$169
This United Airlines deal was found by Cheapflights users on 1/5. 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 7/233:00 pmHHH - ORD
Nonstop2h 45mUnited Airlines
Mon 7/2710:35 amORD - HHH
Nonstop2h 26mUnited Airlines
Deal found 1/5$299
This American Airlines deal was found by Cheapflights users on 1/6. 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 2/113:29 pmHHH - ORD
1 stop5h 21mAmerican Airlines
Sat 2/147:10 amORD - HHH
1 stop6h 12mAmerican Airlines
Deal found 1/6$309
This American Airlines deal was found by Cheapflights users on 1/6. 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 2/216:20 pmHHH - MKE
1 stop6h 35mAmerican Airlines
Sat 2/286:00 amMKE - HHH
1 stop7h 22mAmerican Airlines
Deal found 1/6$336
This American Airlines deal was found by Cheapflights users on 1/5. 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 2/1812:23 pmHHH - ORD
1 stop4h 58mAmerican Airlines
Sun 2/227:58 amORD - HHH
1 stop6h 43mAmerican Airlines
Deal found 1/5$336
This American Airlines deal was found by Cheapflights users on 1/4. 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 1/143:29 pmHHH - ORD
1 stop5h 21mAmerican Airlines
Sat 1/177:21 pmORD - HHH
2 stops15h 59mAmerican Airlines
Deal found 1/4$346
This American Airlines deal was found by Cheapflights users on 1/5. 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 2/166:20 pmHHH - MKE
1 stop6h 35mAmerican Airlines
Fri 2/204:47 pmMKE - HHH
2 stops16h 46mAmerican Airlines
Deal found 1/5$460
This American Airlines deal was found by Cheapflights users on 1/5. 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 1/203:29 pmHHH - MSP
1 stop6h 57mAmerican Airlines
Sat 1/247:43 amMSP - HHH
1 stop6h 16mAmerican Airlines
Deal found 1/5$519

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 January 6, 2026.
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

Tue 2/3

12:51 pm-6:01 pm

1 stop6h 10m

Chicago O'Hare Intl

Tue 2/10

6:05 am-12:20 pm

1 stop5h 15m

$169

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Wed 2/11

12:51 pm-6:01 pm

1 stop6h 10m

Chicago O'Hare Intl

Sat 2/14

8:03 am-2:22 pm

1 stop5h 19m

$309

Hilton Head IslandMilwaukee

HHH - MKE

HHHMKE

Hilton Head Island

Sat 2/21

4:31 pm-11:24 pm

1 stop7h 53m

Milwaukee-Mitchell

Sat 2/28

6:00 am-2:22 pm

1 stop7h 22m

$336

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Thu 2/12

11:03 am-3:21 pm

1 stop5h 18m

Chicago O'Hare Intl

Sat 2/14

5:00 am-10:33 am

1 stop4h 33m

$336

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Wed 2/18

12:23 pm-4:21 pm

1 stop4h 58m

Chicago O'Hare Intl

Sun 2/22

7:58 am-3:41 pm

1 stop6h 43m

$336

Hilton Head IslandMilwaukee

HHH - MKE

HHHMKE

Hilton Head Island

Mon 2/16

6:20 pm-11:55 pm

1 stop6h 35m

Milwaukee-Mitchell

Fri 2/20

4:47 pm-10:33 am

2 stops16h 46m

$460

Hilton Head IslandMinneapolis

HHH - MSP

HHHMSP

Hilton Head Island

Tue 1/20

3:29 pm-9:26 pm

1 stop6h 57m

Minneapolis St Paul

Sat 1/24

7:43 am-2:59 pm

1 stop6h 16m

$519

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Wed 2/4

12:51 pm-8:50 am

2 stops20h 59m

$210

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Wed 3/4

5:19 pm-9:15 am

2 stops16h 56m

$210

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Mon 2/2

3:29 pm-7:50 am

2 stops17h 21m

$210

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/6

Showing 1-10 of 21 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 $284). 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 6h 10m. Fly via American Airlines to get the fastest option. Hilton Head Island and Wisconsin are separated by a distance of 781 mi.

  • 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 - Chicago O'Hare Intl, Hilton Head Island - Milwaukee-Mitchell 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 $284). 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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