$213 Find Cheap Flights from Hilton Head Island to Wisconsin

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Hilton Head Island to Wisconsin departing on 10/21. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy

KAYAK searches hundreds of travel sites at once for deals on flights to Wisconsin

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Hilton Head Island to Wisconsin, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Hilton Head Island to Wisconsin, as well as popular online travel agencies
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Flight Deals

Cheap Flights from Hilton Head Island to Wisconsin

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Milwaukee
Milwaukee1 stop$316
Minneapolis
Minneapolis1 stop$339
Milwaukee
Milwaukee1 stop$316
Minneapolis
Minneapolis1 stop$339

Book Cheap Hilton Head Island to Wisconsin Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Hilton Head Island to Wisconsin that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Hilton Head Island to Wisconsin

Fri, Sep 26 - Mon, Sep 29
Delta Logo
4:05 pm - 10:23 pmHHH-ORD
7h 18m1 stop
Delta Logo
9:50 am - 3:25 pmORD-HHH
4h 35m1 stop
$249Delta
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Thu, Sep 25 - Mon, Sep 29
Delta Logo
12:14 pm - 8:20 pmHHH-ORD
9h 06m2 stops
Delta Logo
7:20 am - 3:25 pmORD-HHH
7h 05m1 stop
$254Delta
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Thu, Sep 25 - Mon, Sep 29
Delta Logo
4:05 pm - 8:35 pmHHH-ORD
5h 30m1 stop
Delta Logo
7:20 am - 3:25 pmORD-HHH
7h 05m1 stop
$274Delta
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Sat, Oct 18 - Sat, Oct 25
American Airlines Logo
5:57 pm - 12:14 amHHH-MKE
7h 17m1 stop
American Airlines Logo
7:12 am - 2:32 pmMKE-HHH
6h 20m1 stop
$316American Airlines
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Sat, Oct 18 - Sat, Oct 25
American Airlines Logo
5:57 pm - 12:14 amHHH-MKE
7h 17m1 stop
American Airlines Logo
6:00 am - 5:27 pmMKE-HHH
10h 27m2 stops
$321American Airlines
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Tue, Nov 18 - Wed, Dec 3
American Airlines Logo
11:28 am - 5:14 pmHHH-MSP
6h 46m1 stop
American Airlines Logo
11:06 am - 6:38 pmMSP-HHH
6h 32m1 stop
$339American Airlines
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Tue, Nov 18 - Wed, Dec 3
American Airlines Logo
11:28 am - 5:14 pmHHH-MSP
6h 46m1 stop
American Airlines Logo
6:00 am - 2:57 pmMSP-HHH
7h 57m2 stops
$344American Airlines
Find Deal
Mon, Sep 8 - Fri, Sep 12
United Airlines Logo
12:06 pm - 8:05 amHHH-ORD
20h 59m2 stops
United Airlines Logo
5:57 pm - 11:25 amORD-HHH
16h 28m2 stops
$516United Airlines
Find Deal
Mon, Sep 8 - Fri, Sep 12
United Airlines Logo
12:06 pm - 5:05 pmHHH-ORD
5h 59m1 stop
United Airlines Logo
3:48 pm - 11:25 amORD-HHH
18h 37m2 stops
$564United Airlines
Find Deal
Fri, Sep 26 - Mon, Sep 29
United Airlines Logo
11:57 am - 12:01 pmHHH-ORD
25h 04m2 stops
United Airlines Logo
10:50 am - 11:16 amORD-HHH
23h 26m2 stops
$1,338United Airlines
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Booking Insights

KAYAK's insights & trends for Hilton Head Island to Wisconsin flights

Get data-powered insights and trends into flights from Hilton Head Island to Wisconsin to help you find the cheapest flights, the best time to fly and much more.

What’s the cheapest day of the week to fly from Hilton Head Island to Wisconsin?

The average price of all round-trip flights from Hilton Head Island to Wisconsin clicked on KAYAK for each day over the last 12 months.

When flying from Hilton Head Island to Wisconsin, you should consider leaving on a Wednesday and avoid Mondays if you are looking for the best rates. For your return to Hilton Head Island, you’ll find the best rates on Wednesdays and the most expensive ones on Thursdays.

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Good to know

Cheapest flight$213
Flight from Hilton Head Island to Chicago

FAQs - booking Wisconsin flights

  • How does KAYAK find such low prices on flights from Hilton Head Island to Wisconsin?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Hilton Head Island to Wisconsin.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Hilton Head Island to Wisconsin?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Hilton Head Island to Wisconsin is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Hilton Head Island to Wisconsin?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly from Hilton Head Island to Wisconsin with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Hilton Head Island to Wisconsin?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying from Hilton Head Island to Wisconsin up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • What is the cheapest time of day to fly to Wisconsin?

    The cheapest time of day to fly to Wisconsin is generally in the evening, when round-trip flights cost $333 on average. Morning departures are around 9% more expensive than evening flights, on average. The most expensive time of day to fly to Wisconsin is generally in the morning, which is peak travel time and where the average cost of a ticket is $363.

Reviews of the top airline flying from Hilton Head Island to Wisconsin

 
See real verified KAYAK customer reviews for airlines flying from Hilton Head Island to Wisconsin. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Hilton Head Island to Wisconsin? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.2
American AirlinesOverall score based on 10000 reviews
7.2Comfort
8.0Crew
6.9Entertainment
6.5Food
7.5Boarding
Airline reviews

My flight was delayed for several hours. Sitting at gate 16 for several hours, I got a text from Kayak the gate changed to 9 before it was announced. Very bad communication at each gate from American Airlines employees. I received 10 notifications of delay from Kayak. My vacation started off horrible! I will write to American Airlines corporate office also.

2.0 MediocreAnonymous, Aug 2025DFW - SAN
Read more American Airlines reviews

My flight was delayed for several hours. Sitting at gate 16 for several hours, I got a text from Kayak the gate changed to 9 before it was announced. Very bad communication at each gate from American Airlines employees. I received 10 notifications of delay from Kayak. My vacation started off horrible! I will write to American Airlines corporate office also.

The AA staff person who checked our bags was curt and almost rude. The FA also seemed unhappy doing her job. Overall it was like riding the school bus back in grade school.

Internet was a bit expensive and did not work ask that week otherwise a good flight

Ring in first class for an overnight flight, there was no blankets nor pillows for first class customers.

My Internet did not work for Outlook email or basically anything. I paid for one hour of in-flight usage and it was terrible. I spent a lot of time on different sites and browsers with no luck and a lot of frustration. Other than that, the flight was on time, crew was nice, service was fine. Seat was OK even though I paid for the extra 6 inches. I cannot imagine how tight the seats in the back must be.

Delayed flight that lead to a missed connection and a 5-hour trip became a 12-hour flight 🙄

Any flight to ORD after about 2pm this summer has been challenging. Flight was delayed getting in (coming from ORD) and that led to it not leaving before a ground stop due to lightening before they could fuel the plane, and so forth. They made up some time but we were still late in arriving at ORD, and that led to missed connections.

Food was ok, but not as good as I have had before on AA.

No issues. They did change our gate FOUR times in about 30 minutes which was mildly annoying but the flight was fine.

Great flight. No issues at all. I still think boarding could be more efficient but otherwise, a good experience.

Everything you need to know for your flight from Hilton Head Island to Wisconsin

Information on your arrival and departure airports

Hilton Head Island (HHH)

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