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Kiawah Island

$58+ 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 2/7. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — CHS
févr. 11 — févr. 181
mer. 2/11
mer. 2/18
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Kiawah Island are usually found in August or July, booked 84 days in advance, depart on a Tuesday or Monday 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 janvier 12, 2026.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$285
(American Airlines)

One-way from

$58
(Cheapflightsfares)

Popular in

March

Cheapest in

August

Average price

$374
Provider with most accurate pricing for Chicago (CHI)-Charleston flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Charleston flights.
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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. 5% potential increase in price ($20 potential increase over avg. RT price).
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Cheapest flight prices on average. 0% potential price decrease ($4 potential savings vs. average RT price).
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Average for round-trip flights in January 2026
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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 janvier 12, 2026.

This Kiwi.com deal was found by Cheapflights users on 1/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ven. 2/136:51 pm
ORD
-
CHS
1 stop20h 04m
Spirit Airlines
mar. 2/175:00 pm
CHS
-
ORD
1 stop8h 40m
Spirit Airlines
Deal found 1/12$281
This Kiwi.com deal was found by Cheapflights users on 1/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jeu. 1/297:20 am
ORD
-
CHS
1 stop9h 16m
Multiple Airlines
sam. 1/316:35 pm
CHS
-
ORD
2 stops17h 12m
Multiple Airlines
Deal found 1/12$282
This Kiwi.com deal was found by Cheapflights users on 1/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 3/238:55 pm
ORD
-
CHS
1 stop13h 22m
Multiple Airlines
sam. 3/285:02 pm
CHS
-
ORD
1 stop8h 05m
Multiple Airlines
Deal found 1/12$284
This United Airlines deal was found by Cheapflights users on 1/12. 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.
sam. 4/46:07 pm
ORD
-
CHS
Nonstop2h 18m
United Airlines
mar. 4/74:55 pm
CHS
-
ORD
Nonstop2h 37m
United Airlines
Deal found 1/12$285
This Kiwi.com deal was found by Cheapflights users on 1/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dim. 3/226:16 pm
ORD
-
CHS
1 stop20h 44m
Spirit Airlines
sam. 3/285:02 pm
CHS
-
ORD
1 stop8h 05m
Spirit Airlines
Deal found 1/12$286
This Kiwi.com deal was found by Cheapflights users on 1/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ven. 2/136:51 pm
ORD
-
CHS
1 stop20h 04m
Spirit Airlines
lun. 2/166:35 pm
CHS
-
ORD
1 stop17h 47m
Spirit Airlines
Deal found 1/12$288
This Cheapflightsfares deal was found by Cheapflights users on 1/12. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jeu. 2/125:15 am
ORD
-
CHS
1 stop11h 25m
Spirit Airlines
dim. 2/155:00 pm
CHS
-
ORD
1 stop8h 40m
Spirit Airlines
Deal found 1/12$290
This Kiwi.com deal was found by Cheapflights users on 1/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sam. 1/245:32 pm
ORD
-
CHS
2 stops14h 06m
Multiple Airlines
dim. 1/255:05 pm
CHS
-
ORD
1 stop17h 07m
Multiple Airlines
Deal found 1/12$292
This Delta deal was found by Cheapflights users on 1/11. 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.
mar. 1/279:35 am
ORD
-
CHS
1 stop10h 31m
Delta
sam. 2/712:02 pm
CHS
-
ORD
1 stop9h 51m
Delta
Deal found 1/11$293
This Southwest deal was found by Cheapflights users on 1/10. 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.
sam. 2/215:15 pm
MDW
-
CHS
1 stop3h 50m
Southwest
mar. 2/249:05 am
CHS
-
MDW
2 stops8h 30m
Southwest
Deal found 1/10$293
This Kiwi.com deal was found by Cheapflights users on 1/11. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jeu. 3/267:05 am
ORD
-
CHS
1 stop15h 21m
Spirit Airlines
mar. 3/317:00 am
CHS
-
ORD
1 stop29h 26m
Spirit Airlines
Deal found 1/11$294
This Kiwi.com deal was found by Cheapflights users on 1/11. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 3/319:30 am
MDW
-
CHS
1 stop5h 37m
Multiple Airlines
mar. 4/73:01 pm
CHS
-
MDW
2 stops9h 41m
Multiple Airlines
Deal found 1/11$294

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 janvier 12, 2026.
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

ven. 2/13

5:05 am-8:49 pm

2 stops14h 44m

Charleston

mer. 2/18

5:00 pm-12:40 am

1 stop8h 40m

$293

ChicagoCharleston

ORD - CHS

ORDCHS

Chicago O'Hare Intl

mer. 2/4

10:36 am-2:02 pm

Nonstop2h 26m

Charleston

sam. 2/7

10:30 am-11:59 am

Nonstop2h 29m

$299

ChicagoCharleston

MDW - CHS

MDWCHS

Chicago Midway

sam. 3/14

2:40 pm-10:00 pm

2 stops6h 20m

Charleston

mar. 3/17

4:35 pm-5:55 pm

Nonstop2h 20m

$303

ChicagoCharleston

MDW - CHS

MDWCHS

Chicago Midway

sam. 4/4

4:35 pm-9:40 pm

1 stop4h 05m

Charleston

sam. 4/11

8:00 am-9:15 am

Nonstop2h 15m

$304

ChicagoCharleston

ORD - CHS

ORDCHS

Chicago O'Hare Intl

mer. 2/4

10:36 am-2:02 pm

Nonstop2h 26m

Charleston

mar. 2/10

2:58 pm-6:37 pm

1 stop4h 39m

$309

ChicagoCharleston

ORD - CHS

ORDCHS

Chicago O'Hare Intl

dim. 3/22

6:16 pm-4:00 pm

1 stop20h 44m

Charleston

ven. 3/27

5:02 pm-12:07 am

1 stop8h 05m

$311

ChicagoCharleston

MDW - CHS

MDWCHS

Chicago Midway

sam. 3/14

2:40 pm-10:00 pm

2 stops6h 20m

Charleston

sam. 3/21

5:30 am-2:20 pm

2 stops9h 50m

$321

ChicagoCharleston

MDW - CHS

MDWCHS

Chicago Midway

ven. 2/20

9:45 am-6:45 pm

2 stops8h 00m

Charleston

sam. 2/21

6:00 am-7:15 am

Nonstop2h 15m

$323

ChicagoCharleston

MDW - CHS

MDWCHS

Chicago Midway

mer. 4/8

5:40 pm-11:55 pm

1 stop5h 15m

Charleston

sam. 4/11

5:27 am-9:56 am

1 stop5h 29m

$325

ChicagoCharleston

ORD - CHS

ORDCHS

Chicago O'Hare Intl

sam. 2/28

10:35 am-1:52 pm

Nonstop2h 17m

Charleston

lun. 3/2

10:05 am-2:21 pm

1 stop5h 16m

$325

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/11

Showing 1-10 of 42 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 January 9, 2026.

The best time to book flights from Chicago to Kiawah Island is 84 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, May is the cheapest month in which you can book a flight from Chicago to Kiawah Island (average of $46). Flying from Chicago to Kiawah Island in March 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.

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 janvier 12, 2026.

When flying from Chicago to Kiawah Island, the time of day you fly usually plays a role in the price. Save by searching for a flight in the morning, which can drop the price by up to 10% versus a flight in the evening.

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 January 10, 2026.

Travelers seeking maximum savings on their Chicago to Kiawah Island flight should consider departing on Thursday afternoons when fares are most often at their lowest. Sunday evenings 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 janvier 12, 2026.

The most flights from CHI to K1A are scheduled on a Thursday (18 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (7 on average).

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 janvier 12, 2026.
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
4,256 reviews

Crew

8.6

Entertainment

7.5

Food

7.0

Boarding

8.1

Comfort

8.0

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Southwest
8.0
Very good
4,256 reviews
Southwest
8.0
Very good
4,256 reviews

Crew

8.6

Entertainment

7.5

Food

7.0

Boarding

8.1

Comfort

8.0

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Delta
7.9
Good
8,039 reviews
Southwest
8.0
Very good
4,256 reviews

Crew

8.6

Entertainment

7.5

Food

7.0

Boarding

8.1

Comfort

8.0

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
United Airlines
7.4
Good
9,149 reviews
Southwest
8.0
Very good
4,256 reviews

Crew

8.6

Entertainment

7.5

Food

7.0

Boarding

8.1

Comfort

8.0

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
American Airlines
7.2
Good
11,114 reviews
Southwest
8.0
Very good
4,256 reviews

Crew

8.6

Entertainment

7.5

Food

7.0

Boarding

8.1

Comfort

8.0

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Spirit Airlines
6.3
Okay
8,303 reviews
Southwest
8.0
Very good
4,256 reviews

Crew

8.6

Entertainment

7.5

Food

7.0

Boarding

8.1

Comfort

8.0

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

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.

  • How long is the flight from Chicago to Kiawah Island?

    Departing from Chicago to Kiawah Island will take you 2h 26m. The distance between Chicago and Kiawah Island is about 760 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • 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 $124 on United Airlines. Other airlines that offer cheap prices include American Airlines from $133 and Southwest from $160 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 Emirates (80%), Envoy Air (79%) and Qatar Airways (74%).

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

    On average you can expect to pay $455 for a flight from Chicago to Kiawah Island. The cheapest flight overall is $124 while the most popular route, (Chicago O'Hare Intl - Charleston) is currently priced at $109.

  • 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, May is the cheapest month in which you can book a flight from Chicago to Kiawah Island (average of $46). Flying from Chicago to Kiawah Island in March 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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Alternative routes for Chicago to Kiawah Island

See prices for flight routes from nearby airports that may be better suited for you.
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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 janvier 12, 2026.
AirlineCheapestAverageFlexibilityOn-time
Allegiant AirCheapest$46Average$92FlexibilityNo cancel feeOn-time88%
DeltaCheapest$98Average$360FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$143Average$386FlexibilityNo cancel feeOn-time71%
Spirit AirlinesCheapest$157Average$185FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$227Average$438FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$245Average$346FlexibilityNo cancel feeOn-time63%

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