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$177+ 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 5/19. Fares are subject to change and may not be available on all flights or dates of travel.
HHH — MKE
Mar 23 — Mar 301
Mon 3/23
Mon 3/30
1 adult, Economy
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Cheap 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 February 21, 2026.

This Delta deal was found by Cheapflights users on 2/18. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/112:08 pm
HHH
-
ORD
1 stop7h 27m
Delta
Sun 5/38:15 am
ORD
-
HHH
1 stop6h 05m
Delta
Deal found 2/18$248
This United Airlines deal was found by Cheapflights users on 2/20. 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.
Wed 4/13:05 pm
HHH
-
MKE
1 stop7h 13m
United Airlines
Mon 4/66:50 am
MKE
-
HHH
1 stop6h 26m
United Airlines
Deal found 2/20$274
This United Airlines deal was found by Cheapflights users on 2/20. 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.
Fri 7/33:05 pm
HHH
-
MKE
1 stop4h 46m
United Airlines
Tue 7/77:30 am
MKE
-
HHH
1 stop5h 51m
United Airlines
Deal found 2/20$289
This American Airlines deal was found by Cheapflights users on 2/18. 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 5/164:10 pm
HHH
-
ORD
1 stop6h 11m
American Airlines
Sat 5/305:00 am
ORD
-
HHH
1 stop7h 06m
American Airlines
Deal found 2/18$329
This American Airlines deal was found by Cheapflights users on 2/20. 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 4/12:58 pm
HHH
-
MKE
2 stops9h 26m
American Airlines
Mon 4/67:06 am
MKE
-
HHH
1 stop6h 16m
American Airlines
Deal found 2/20$334
This American Airlines deal was found by Cheapflights users on 2/20. 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 pm
HHH
-
MKE
1 stop6h 35m
American Airlines
Sat 2/288:00 am
MKE
-
HHH
2 stops8h 44m
American Airlines
Deal found 2/20$359
This United Airlines deal was found by Cheapflights users on 2/21. 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 4/93:05 pm
HHH
-
ORD
Nonstop2h 44m
United Airlines
Tue 4/1410:50 am
ORD
-
HHH
Nonstop2h 26m
United Airlines
Deal found 2/21$379
This American Airlines deal was found by Cheapflights users on 2/20. 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 3/72:58 pm
HHH
-
ORD
1 stop5h 42m
American Airlines
Wed 3/1110:28 am
ORD
-
HHH
1 stop6h 16m
American Airlines
Deal found 2/20$389
This American Airlines deal was found by Cheapflights users on 2/19. 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 2/266:20 pm
HHH
-
ORD
1 stop6h 56m
American Airlines
Sat 2/289:38 am
ORD
-
HHH
1 stop5h 23m
American Airlines
Deal found 2/19$417
This United Airlines deal was found by Cheapflights users on 2/20. 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.
Sat 6/131:45 pm
HHH
-
ORD
1 stop7h 20m
United Airlines
Fri 6/1910:45 am
ORD
-
HHH
Nonstop2h 36m
United Airlines
Deal found 2/20$423
This American Airlines deal was found by Cheapflights users on 2/20. 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 2/212:58 pm
HHH
-
MSP
2 stops10h 06m
American Airlines
Wed 2/256:15 am
MSP
-
HHH
1 stop7h 46m
American Airlines
Deal found 2/20$424
This American Airlines deal was found by Cheapflights users on 2/20. 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.
Fri 7/32:48 pm
HHH
-
MKE
1 stop4h 01m
American Airlines
Tue 7/75:00 am
MKE
-
HHH
2 stops11h 09m
American Airlines
Deal found 2/20$426

Find 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 February 21, 2026.

Round-trip from

$248
(Delta)

One-way from

$177
(Delta)
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 February 21, 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

Fri 5/1

12:08 pm-6:35 pm

1 stop7h 27m

Chicago O'Hare Intl

Sun 5/3

8:15 am-3:20 pm

1 stop6h 05m

$248

Hilton Head IslandMilwaukee

HHH - MKE

HHHMKE

Hilton Head Island

Fri 7/3

3:05 pm-6:51 pm

1 stop4h 46m

Milwaukee-Mitchell

Tue 7/7

7:30 am-2:21 pm

1 stop5h 51m

$289

Hilton Head IslandMilwaukee

HHH - MKE

HHHMKE

Hilton Head Island

Wed 4/1

2:58 pm-11:24 pm

2 stops9h 26m

Milwaukee-Mitchell

Mon 4/6

7:06 am-2:22 pm

1 stop6h 16m

$334

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Sat 5/16

2:54 pm-7:22 pm

1 stop5h 28m

Chicago O'Hare Intl

Sat 5/30

10:16 am-1:46 pm

Nonstop2h 30m

$366

Hilton Head IslandMilwaukee

HHH - MKE

HHHMKE

Hilton Head Island

Fri 7/3

2:48 pm-5:49 pm

1 stop4h 01m

Milwaukee-Mitchell

Tue 7/7

5:00 am-5:09 pm

2 stops11h 09m

$426

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Sat 3/7

2:58 pm-10:46 pm

2 stops8h 48m

Chicago O'Hare Intl

Wed 3/11

9:48 am-5:44 pm

2 stops6h 56m

$432

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Thu 3/5

2:58 pm-7:40 pm

1 stop5h 42m

Chicago O'Hare Intl

Mon 3/9

5:00 am-10:33 am

1 stop4h 33m

$445

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Thu 6/4

3:05 pm-4:51 pm

Nonstop2h 46m

Chicago O'Hare Intl

Fri 6/5

10:45 am-2:21 pm

Nonstop2h 36m

$447

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Tue 4/7

3:05 pm-4:49 pm

Nonstop2h 44m

Chicago O'Hare Intl

Thu 4/9

10:50 am-2:16 pm

Nonstop2h 26m

$447

Hilton Head IslandMinneapolis

HHH - MSP

HHHMSP

Hilton Head Island

Fri 3/6

11:03 am-9:21 pm

2 stops11h 18m

Minneapolis St Paul

Sun 3/8

10:10 am-5:44 pm

1 stop6h 34m

$460

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/21

Showing 1-10 of 37 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 February is currently the most expensive (average of $257). 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 4h 46m. Fly via Delta, United Airlines, or American Airlines to get the fastest option. Hilton Head Island and Wisconsin are separated by a distance of 838 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 - Chicago O'Hare Intl, Hilton Head Island - Minneapolis St Paul or Hilton Head Island - Milwaukee-Mitchell 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 February is currently the most expensive (average of $257). 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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