$275 Find Cheap Flights from Canada to Hilton Head Island

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to Hilton Head Island departing on 10/24. 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 Hilton Head Island

 
These are the airlines KAYAK users have selected most often from within our search results for flights to Hilton Head Island, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results for flights to Hilton Head Island, as well as popular online travel agencies
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Cheap Flights from Canada to Hilton Head Island

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Canada to Hilton Head Island 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 Canada to Hilton Head Island

Mon, Mar 16 - Mon, Mar 23
American Airlines Logo
5:40 am - 10:24 amYYZ-HHH
4h 44m1 stop
American Airlines Logo
6:25 pm - 3:00 pmHHH-YYZ
20h 35m1 stop
$561American Airlines
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Tue, Oct 14 - Tue, Oct 28
American Airlines Logo
7:15 pm - 12:15 pmYYZ-HHH
17h 00m2 stops
American Airlines Logo
5:21 pm - 9:59 amHHH-YYZ
16h 38m2 stops
$629American Airlines
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Everything you should know

When to travel
December
Cheapest • 11% price drop
November
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Cheapest round-trip
$561
Overall average: $529
American Airlines
Mon 3/16Mon 3/23
YYZ - HHH • 1 stop
Cheapest one-way
$275
American Airlines
Fri 10/24
YYZ - HHH • 2 stops
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KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Hilton Head Island!
Booking Insights

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

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

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for flights to Hilton Head Island, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights to Hilton Head Island is January, where tickets cost $516 on average for one-way flights. On the other hand, the most expensive months are August and October, where the average cost of tickets from Canada is $885 and $670 respectively. For return trips, the best month to travel is December with an average price of $530.

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FAQs - booking Hilton Head Island flights

  • How far is Hilton Head Island Airport from central Hilton Head Island?

    Hilton Head Island Airport is 3 miles from the center of Hilton Head Island.

  • What is the name of Hilton Head Island’s airport?

    There is only 1 airport in Hilton Head Island, called Hilton Head Island Airport (HHH). It can also be referred to as Hilton Head.

  • What is the cheapest day to fly to Hilton Head Island?

    Based on KAYAK data, the cheapest day to fly to Hilton Head Island is Tuesday where tickets can be as cheap as $536. On the other hand, the most expensive day to fly is Sunday, where prices are $649 on average.

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

    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 to Hilton Head Island.

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

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

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

    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 to Hilton Head Island 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 to Hilton Head Island?

    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 to Hilton Head Island 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 Hilton Head Island?

    The cheapest time of day to fly to Hilton Head Island is generally in the morning, when flights cost $630 on average. The most expensive time of day to fly to Hilton Head Island is generally in the afternoon, which is peak travel time and where the average cost of a ticket is $730.

  • How many direct flights to Hilton Head Island are there each week?

    Each week there are around 56 direct flights from within Canada to Hilton Head Island. The most common day for departures is Thursday, with 16% of flights taking off on this day.

Top tips for finding cheap flights to Hilton Head Island

  • Enter your preferred departure airport and travel dates into the search form above to unlock the latest Hilton Head Island flight deals.

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

 
See real verified KAYAK customer reviews for airlines flying to Hilton Head Island. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline from Canada to Hilton Head Island. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with to Hilton Head Island? 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 11033 reviews
7.5Boarding
8.0Crew
6.9Entertainment
7.2Comfort
6.4Food
Airline reviews

We spent too much time on board waiting for takeoff.

6.0 GoodAnonymous, Oct 2025MEX - CLT
Read more American Airlines reviews

We spent too much time on board waiting for takeoff.

Very below average , plane from Dallas to Toyko was very poor designed plane. I had to sit for 13 hours next to fat man. Really bad seat and entertainment screen sucked

It was a red eye flight, so no meals were provided, but it was fine with snacks. The seats felt cramped and almost too narrow.

The Phildalphia to Allentown portion was a BUS, not a plane. All was as expected.

Very crowded flight but what can you expect these days?? Crew was accommodating.

We didn't take off until an hour after we boarded.

The flight crew was rude. We were in first class and no one even offered water until an hour after we were in the air. Horrible experience

Premium economy seat was decent. As always poor headphones, poor food and beverage, crew is not overly friendly

Excellent - explanations were clear staff was nice and flight was comfortable

The flight was fine. This survey is not. There is no option for N/A so items which don’t apply to my experience still must be rated. In those instances I give a “3” rating which ultimately skews the results.

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

Information on the airport you'll fly into in Hilton Head Island

Hilton Head Island (HHH)

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