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Kiawah Island

$69+ Cheap flights from Chicago (CHI) to Kiawah Island, SC

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 9/11. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — CHS
Jul 8 — Jul 151
Tue 7/8
Tue 7/15
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Kiawah Island are usually found in August or September, booked 68 days in advance, depart on a Tuesday or Saturday and return on a Friday

Cheap flight deals from Chicago to Kiawah Island

Keep the following information in mind while searching for Chicago to Kiawah Island flight deals. Data was last updated July 3, 2025.

Round-trip from

$261
(United Airlines)

One-way from

$69
(Priceline)

Popular in

December

Cheapest in

August

Average price

$367
From Chicago (CHI) to Kiawah Island
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One-way flight from Chicago (CHI) to Kiawah Island
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Highest demand for flights based on searches. 12% potential increase in price ($56 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($11 potential savings vs. average RT price).
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Average for round-trip flights in July 2025
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Find flight deals from Chicago to Kiawah Island

Cheapest flights from Chicago to Kiawah Island
Explore the most affordable flight options available from Chicago to Kiawah Island. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 3, 2025.

This United Airlines deal was found by Cheapflights users on 7/3. 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 8/77:00 amORD - CHS
Nonstop2h 23mUnited Airlines
Tue 8/1210:00 amCHS - ORD
1 stop5h 33mUnited Airlines
Deal found 7/3$261
This American Airlines deal was found by Cheapflights users on 7/1. 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 7/318:24 pmORD - CHS
Nonstop2h 35mAmerican Airlines
Wed 8/65:10 pmCHS - ORD
Nonstop2h 36mAmerican Airlines
Deal found 7/1$262
This Southwest deal was found by Cheapflights users on 7/1. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/257:35 pmMDW - CHS
Nonstop2h 05mSouthwest
Sun 9/288:40 amCHS - MDW
Nonstop2h 10mSouthwest
Deal found 7/1$263
This Delta deal was found by Cheapflights users on 7/1. 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.
Sun 8/315:45 amORD - CHS
1 stop5h 05mDelta
Tue 9/27:00 amCHS - ORD
1 stop15h 47mDelta
Deal found 7/1$264
This Mytrip deal was found by Cheapflights users on 7/1. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/185:05 amORD - CHS
1 stop8h 40mSpirit Airlines
Mon 7/2110:53 amCHS - ORD
2 stops13h 51mSpirit Airlines
Deal found 7/1$265
This Southwest deal was found by Cheapflights users on 7/2. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/77:30 amORD - CHS
2 stops14h 25mSouthwest
Sat 9/1310:55 amCHS - ORD
2 stops12h 05mSouthwest
Deal found 7/2$269
This FlightHub deal was found by Cheapflights users on 7/1. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/48:15 amMDW - CHS
1 stop5h 16mFrontier
Sun 9/73:26 pmCHS - MDW
1 stop16h 50mFrontier
Deal found 7/1$270
This Delta deal was found by Cheapflights users on 7/1. 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 8/296:17 pmMDW - CHS
1 stop4h 38mDelta
Tue 9/25:35 pmCHS - MDW
1 stop4h 51mDelta
Deal found 7/1$272
This Mytrip deal was found by Cheapflights users on 7/1. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/265:05 amORD - CHS
1 stop14h 48mMultiple Airlines
Wed 7/307:00 amCHS - ORD
1 stop16h 32mMultiple Airlines
Deal found 7/1$278
This Frontier deal was found by Cheapflights users on 7/3. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/102:54 pmORD - CHS
2 stops16h 12mFrontier
Mon 7/149:05 amCHS - ORD
1 stop11h 22mFrontier
Deal found 7/3$301

Cheapflights Fare Finder

Customize your flight search to find flights from Chicago to Kiawah Island 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 July 3, 2025.
Use the filters below to find and compare flights from Chicago to Kiawah Island that are best for you.

Fly from

Chicago

Fly to

Kiawah Island

Route

Depart

Return

Price

ChicagoCharleston

ORD - CHS

ORDCHS

Chicago O'Hare Intl

Thu 8/7

7:00 am-10:23 am

Nonstop2h 23m

Charleston

Tue 8/12

10:00 am-2:33 pm

1 stop5h 33m

$261

ChicagoCharleston

ORD - CHS

ORDCHS

Chicago O'Hare Intl

Thu 7/31

8:24 pm-11:59 pm

Nonstop2h 35m

Charleston

Wed 8/6

5:10 pm-6:46 pm

Nonstop2h 36m

$262

ChicagoCharleston

MDW - CHS

MDWCHS

Chicago Midway

Thu 9/25

7:35 pm-10:40 pm

Nonstop2h 05m

Charleston

Sun 9/28

8:40 am-9:50 am

Nonstop2h 10m

$263

ChicagoCharleston

ORD - CHS

ORDCHS

Chicago O'Hare Intl

Sun 8/31

5:45 am-11:50 am

1 stop5h 05m

Charleston

Tue 9/2

7:00 am-9:47 pm

1 stop15h 47m

$264

ChicagoCharleston

ORD - CHS

ORDCHS

Chicago O'Hare Intl

Fri 7/18

5:05 am-2:45 pm

1 stop8h 40m

Charleston

Mon 7/21

10:53 am-11:44 pm

2 stops13h 51m

$265

ChicagoCharleston

ORD - CHS

ORDCHS

Chicago O'Hare Intl

Sun 9/7

7:30 am-10:55 pm

2 stops14h 25m

Charleston

Sat 9/13

10:55 am-10:00 pm

2 stops12h 05m

$269

ChicagoCharleston

MDW - CHS

MDWCHS

Chicago Midway

Thu 9/4

8:15 am-2:31 pm

1 stop5h 16m

Charleston

Sun 9/7

3:26 pm-7:16 am

1 stop16h 50m

$270

ChicagoCharleston

MDW - CHS

MDWCHS

Chicago Midway

Fri 8/29

6:17 pm-11:55 pm

1 stop4h 38m

Charleston

Tue 9/2

5:35 pm-9:26 pm

1 stop4h 51m

$272

ChicagoCharleston

ORD - CHS

ORDCHS

Chicago O'Hare Intl

Sat 7/26

5:05 am-8:53 pm

1 stop14h 48m

Charleston

Wed 7/30

7:00 am-10:32 pm

1 stop16h 32m

$278

ChicagoCharleston

ORD - CHS

ORDCHS

Chicago O'Hare Intl

Thu 9/11

6:10 am-2:31 pm

1 stop7h 21m

$69

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/2

Showing 1-10 of 21 results
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Best time to book a flight from Chicago to Kiawah Island

Have a flexible travel schedule? Discover the best time to fly to Kiawah Island from Chicago 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 Chicago to Kiawah Island

How far ahead should I book a flight from Chicago to Kiawah Island?

Use this chart to determine the optimal time to book a round-trip flight from Chicago to Kiawah Island. Price data was last updated on June 27, 2025.

The best time to book flights from Chicago to Kiawah Island is 68 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.

What is the cheapest month to book a flight from Chicago to Kiawah Island?

Currently, August is the cheapest month in which you can book a flight from Chicago to Kiawah Island (average of $217). Flying from Chicago to Kiawah Island in March is currently the most expensive (average of $335). 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.

What is the cheapest time of day to fly from CHI to K1A?

Find hourly flight availability from Chicago to Kiawah Island. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated July 3, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chicago to Kiawah Island as you normally would.

What is the cheapest day to fly from Chicago to Kiawah Island?

Use this chart to determine the cheapest time to fly round-trip from Chicago to Kiawah Island. Price data was last updated on October 27, 2024.

Travelers seeking maximum savings on their Chicago to Kiawah Island flight should consider departing on Saturday at noon when fares are most often at their lowest. Thursday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from Chicago to Kiawah Island

Explore weekly flight availability from Chicago to Kiawah Island. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated July 3, 2025.

The most flights from CHI to K1A are scheduled on a Thursday (20 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (4 on average).

How much does it cost to fly round-trip from Chicago to Kiawah Island?

Reviews of airlines servicing Kiawah Island

Get insights into the airlines that provide service to Kiawah Island. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Kiawah Island. Reviews last updated July 3, 2025.
Get a feel of what it's like to fly with Southwest, Delta, and United Airlines from Chicago to Kiawah Island by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,266 reviews

Boarding

8.2

Entertainment

7.6

Comfort

8.0

Food

7.0

Overall

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Southwest
8.0
Very good
4,266 reviews
Southwest
8.0
Very good
4,266 reviews

Boarding

8.2

Entertainment

7.6

Comfort

8.0

Food

7.0

Overall

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Delta
8.0
Very good
7,982 reviews
Southwest
8.0
Very good
4,266 reviews

Boarding

8.2

Entertainment

7.6

Comfort

8.0

Food

7.0

Overall

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
United Airlines
7.4
Good
8,861 reviews
Southwest
8.0
Very good
4,266 reviews

Boarding

8.2

Entertainment

7.6

Comfort

8.0

Food

7.0

Overall

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
JetBlue
7.3
Good
2,916 reviews
Southwest
8.0
Very good
4,266 reviews

Boarding

8.2

Entertainment

7.6

Comfort

8.0

Food

7.0

Overall

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,266 reviews

Boarding

8.2

Entertainment

7.6

Comfort

8.0

Food

7.0

Overall

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

Related info for your journey

Find useful and relevant information for your journey from Chicago to Kiawah Island. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What are the cheapest airlines to fly from Chicago to Kiawah Island one-way?

    One-way options have recently been found by users for as low as $69 on Frontier. Other airlines that offer cheap prices include American Airlines from $91 and Southwest from $91 one-way.

  • What are the most reliable airlines from Chicago to Kiawah Island?

    The top 3 most reliable airlines when flying from Chicago to Kiawah Island are Republic Airways (100%), United Airlines (89%) and Air Canada (88%).

  • What are the cheapest flights from Chicago to Kiawah Island?

    On average you can expect to pay $351 for a flight from Chicago to Kiawah Island. The cheapest flight overall is $107 while the most popular route, (Chicago O'Hare Intl - Charleston) is currently priced at $181.

  • Can I find deals for flights from Chicago to Kiawah Island that include hotel bookings?

    Yes. In addition to deals on Chicago to Kiawah Island flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Kiawah Island?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Kiawah Island.

  • Can I find deals for business class flights from Chicago to Kiawah Island?

    Yes. Cheapflights offers flight deals from Chicago to Kiawah Island 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 Chicago to Kiawah Island?

    Currently, August is the cheapest month in which you can book a flight from Chicago to Kiawah Island (average of $217). Flying from Chicago to Kiawah Island in March is currently the most expensive (average of $335). 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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Top 6 airlines flying from Chicago to Kiawah Island

Discover the top 6 airlines that operate flights from Chicago to Kiawah Island. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated July 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
Allegiant AirCheapest$51Average$95FlexibilityNo cancel feeOn-time88%
Spirit AirlinesCheapest$124Average$198FlexibilityNo cancel feeOn-time65%
DeltaCheapest$153Average$386FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$158Average$379FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$176Average$393FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$231Average$454FlexibilityNo cancel feeOn-time69%

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