Kiawah Island Vacations

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Kiawah Island Flight + Hotel packages

Price found within the past 48 hours. Click for updated prices.
The Ryder Hotel

The Ryder Hotel

Charleston Historic District
$1,065
per person
Nov 22 - Nov 28
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Charleston (CHS)
Stay at this hotel in Charleston. Enjoy 2 bars/lounges, breakfast (surcharge), and 24-hour room service. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Charleston City Market and Waterfront Park are located nearby.
The Francis Marion Hotel

The Francis Marion Hotel

Charleston Historic District
$1,121
per person
Nov 22 - Nov 28
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Charleston (CHS)
Book a stay at this luxury hotel in Charleston. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Charleston City Market and South Carolina Aquarium are located nearby.
Parking was a scam, the sign reads $24 per day, however the small print reads it starts at 12 midnight for 24 hrs not based on actual time you enter. You pay for 2 days and only been parked for 1

Reviewed on Oct 20, 2026

The Charleston Place

The Charleston Place

Charleston Historic District
Save 100% on your flight
$2,080
per person
Nov 22 - Nov 28
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Charleston (CHS)
Book a stay at this luxury hotel in Charleston. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Charleston City Market and Waterfront Park are located nearby.
To have a luxury hotel like this that is privately owned and not a massive corporate feel is awesome. We love the Charleston place and all the changes they have been making over the past few years. Beautiful property great vibe and quiet luxury.

Reviewed on Oct 18, 2026

Emeline

Emeline

Charleston Historic District
$1,262
per person
Nov 22 - Nov 28
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Charleston (CHS)
Book a stay at this luxury hotel in Charleston. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Charleston City Market and Waterfront Park are located nearby.
The Ansonborough

The Ansonborough

Charleston Historic District
$1,390
per person
Nov 22 - Nov 28
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Charleston (CHS)
Book a stay at this business-friendly hotel in Charleston. Enjoy free breakfast, free WiFi, and a rooftop terrace. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Charleston City Market and Waterfront Park are located nearby.
The Cooper

The Cooper

Charleston Historic District
Save 100% on your flight
$2,846
per person
Nov 22 - Nov 28
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Charleston (CHS)
Book a stay at this luxury hotel in Charleston. Enjoy free WiFi, a full-service spa, and 3 restaurants. Popular attractions Waterfront Park and Charleston City Market are located nearby.
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Kiawah Island Vacation Packages

Trying to figure out a way to package your Kiawah Island flight and hotel, while saving some money? The AARP Travel Center Powered by Expedia® Kiawah Island vacation packages can help. We can assist you with hotel bookings, flights, car rentals and more. You can get almost everything you need here to make your trip to Kiawah Island perfect. Our Travel Center is a one-stop shop where you can put together the best vacation package for you. We have an amazing selection of flights and lodgings, as well as Kiawah Island things to do to choose from.

Kiawah Island Hotels

You can choose from around 885 hotels. Whether you want to stay in the heart of the city or pick a spot that is near all the Kiawah Island hot spots, we have plenty of options available.

We have competitive rates on everything from luxury hotels that check off all the vacation must-haves to affordable accommodations which are great for those on a budget. You can browse all the possibilities and pick the lodging that is perfect for you and your family. With AARP Travel Center's Kiawah Island hotel packages, you not only get a great rate on your flight, but also a great place to stay.

Things to do in Kiawah Island

Kiawah Island is the ideal spot when you wish to a break from it all. With only around 1,749 people in the city, this hidden-gem is good for a quite vacation. If you want to take walk through the past, then you are in luck as Kiawah Island has a noteworthy historic district.

The AARP Travel Center "Things to Do" page has more great activities that you can book.

Package Your Kiawah Island Vacation and Save

With so much happening in Kiawah Island, you'll be wanting to focus on your outings, not devoting time to finding the hotel with the lowest rate. AARP Travel Center allows you to quickly get everything you want, and save money while doing it. You can plan your entire trip, including things to do in Kiawah Island from only one site. The hardest packing you'll have to do is for your suitcase. Book now and save!

Top Flight Deals

These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Breeze Airways
JetBlue Airways
Delta
Wed, Feb 3 - Sat, Feb 6
JFK
John F. Kennedy Intl.
CHS
Charleston Intl.
$229
Roundtrip
found 15 hours ago
Select Delta flight, departing Wed, Feb 3 from John F. Kennedy Intl. to Charleston Intl., returning Sat, Feb 6, priced at $229 found 15 hours ago
American Airlines
United