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Kiawah Island

$57+ 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 10/18. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — CHS
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
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 85 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 September 15, 2025.

Round-trip from

$235
(Kiwi.com)

One-way from

$57
(Cheapflightsfares)

Popular in

December

Cheapest in

August

Average price

$381
From Chicago (CHI) to Kiawah Island
Search Deals
One-way flight from Chicago (CHI) to Kiawah Island
Search Deals
Highest demand for flights based on searches. 13% potential increase in price ($62 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($10 potential savings vs. average RT price).
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Average for round-trip flights in September 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 September 15, 2025.

This Kiwi.com deal was found by Cheapflights users on 9/14. 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.
Tue 9/305:46 pmORD - CHS
1 stop19h 43mMultiple Airlines
Sun 10/510:11 amCHS - ORD
1 stop25h 39mMultiple Airlines
Deal found 9/14$235
This KAYAK deal was found by Cheapflights users on 9/14. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/26:44 pmORD - CHS
1 stop13h 21mSpirit Airlines
Mon 10/610:11 amCHS - ORD
1 stop9h 27mSpirit Airlines
Deal found 9/14$236
This KAYAK deal was found by Cheapflights users on 9/13. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/186:00 amORD - CHS
2 stops11h 41mSpirit Airlines
Mon 10/2010:11 amCHS - ORD
1 stop14h 34mSpirit Airlines
Deal found 9/13$237
This Kiwi.com deal was found by Cheapflights users on 9/14. 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.
Tue 11/112:47 pmORD - CHS
1 stop19h 00mMultiple Airlines
Tue 11/182:59 pmCHS - ORD
1 stop7h 24mMultiple Airlines
Deal found 9/14$239
This Kiwi.com deal was found by Cheapflights users on 9/13. 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.
Thu 9/258:05 amORD - CHS
2 stops24h 00mMultiple Airlines
Sun 9/2812:08 pmCHS - ORD
1 stop23h 44mMultiple Airlines
Deal found 9/13$240
This Kiwi.com deal was found by Cheapflights users on 9/13. 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.
Thu 9/258:05 amORD - CHS
2 stops24h 00mMultiple Airlines
Tue 9/302:59 pmCHS - ORD
1 stop7h 59mMultiple Airlines
Deal found 9/13$241
This KAYAK deal was found by Cheapflights users on 9/14. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/177:51 pmORD - CHS
2 stops21h 50mSpirit Airlines
Sun 10/1910:11 amCHS - ORD
1 stop14h 34mSpirit Airlines
Deal found 9/14$242
This Kiwi.com deal was found by Cheapflights users on 9/14. 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.
Wed 11/125:59 pmORD - CHS
1 stop15h 46mSpirit Airlines
Mon 11/1711:40 amCHS - ORD
2 stops13h 02mSpirit Airlines
Deal found 9/14$243
This Kiwi.com deal was found by Cheapflights users on 9/15. 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.
Mon 11/106:30 pmORD - CHS
2 stops13h 07mMultiple Airlines
Sun 11/165:40 pmCHS - ORD
1 stop16h 43mMultiple Airlines
Deal found 9/15$244
This United Airlines deal was found by Cheapflights users on 9/12. 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.
Wed 10/88:50 amORD - CHS
1 stop5h 13mUnited Airlines
Sun 10/126:02 amCHS - ORD
Nonstop2h 28mUnited Airlines
Deal found 9/12$245
This Kiwi.com deal was found by Cheapflights users on 9/13. 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.
Mon 11/106:30 pmORD - CHS
2 stops13h 07mMultiple Airlines
Tue 11/182:59 pmCHS - ORD
1 stop7h 24mMultiple Airlines
Deal found 9/13$246
This Kiwi.com deal was found by Cheapflights users on 9/13. 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.
Sat 9/276:44 pmORD - CHS
1 stop15h 01mMultiple Airlines
Mon 9/293:33 pmCHS - ORD
1 stop7h 25mMultiple Airlines
Deal found 9/13$247

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 September 15, 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 10/23

7:10 am-10:35 am

Nonstop2h 25m

Charleston

Mon 10/27

6:15 am-7:47 am

Nonstop2h 32m

$256

ChicagoCharleston

ORD - CHS

ORDCHS

Chicago O'Hare Intl

Tue 10/28

7:00 am-1:19 pm

1 stop5h 19m

Charleston

Thu 10/30

2:15 pm-8:52 pm

1 stop7h 37m

$277

ChicagoCharleston

ORD - CHS

ORDCHS

Chicago O'Hare Intl

Wed 10/8

10:35 am-2:07 pm

Nonstop2h 32m

Charleston

Sun 10/12

6:02 am-7:30 am

Nonstop2h 28m

$290

ChicagoCharleston

ORD - CHS

ORDCHS

Chicago O'Hare Intl

Mon 10/20

5:51 pm-10:41 pm

1 stop3h 50m

Charleston

Thu 10/23

8:03 pm-11:58 pm

1 stop4h 55m

$293

ChicagoCharleston

ORD - CHS

ORDCHS

Chicago O'Hare Intl

Mon 12/1

4:21 pm-10:48 pm

1 stop5h 27m

Charleston

Tue 12/2

2:55 pm-8:39 pm

1 stop6h 44m

$293

ChicagoCharleston

ORD - CHS

ORDCHS

Chicago O'Hare Intl

Sat 10/11

4:50 pm-8:08 pm

Nonstop2h 18m

Charleston

Mon 10/13

6:02 am-7:30 am

Nonstop2h 28m

$293

ChicagoCharleston

ORD - CHS

ORDCHS

Chicago O'Hare Intl

Tue 11/11

10:40 am-1:55 pm

Nonstop2h 15m

Charleston

Mon 11/17

6:15 am-7:47 am

Nonstop2h 32m

$293

ChicagoCharleston

ORD - CHS

ORDCHS

Chicago O'Hare Intl

Sat 10/11

4:50 pm-8:08 pm

Nonstop2h 18m

Charleston

Sat 10/18

6:02 am-7:30 am

Nonstop2h 28m

$293

ChicagoCharleston

ORD - CHS

ORDCHS

Chicago O'Hare Intl

Sat 11/8

7:10 am-10:29 am

Nonstop2h 19m

Charleston

Wed 11/12

4:38 pm-6:10 pm

Nonstop2h 32m

$293

ChicagoCharleston

MDW - CHS

MDWCHS

Chicago Midway

Sun 9/28

6:21 am-2:28 pm

1 stop7h 07m

Charleston

Wed 10/1

8:10 pm-3:58 pm

2 stops20h 48m

$302

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/12

Showing 1-10 of 40 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 September 12, 2025.

The best time to book flights from Chicago to Kiawah Island is 85 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 September 15, 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 Monday evenings when fares are most often at their lowest. Sunday mornings 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 September 15, 2025.

The most flights from CHI to K1A are scheduled on a Sunday (16 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (11 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 September 15, 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
4,242 reviews

Comfort

8.0

Food

7.0

Overall

8.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Food

7.0

Overall

8.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Delta
8.0
Very good
7,954 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Food

7.0

Overall

8.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
United Airlines
7.4
Good
8,929 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Food

7.0

Overall

8.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Food

7.0

Overall

8.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Spirit Airlines
6.3
Okay
8,015 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Food

7.0

Overall

8.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

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. The distance between Chicago and Kiawah Island is about 745 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 $67 on United Airlines. Other airlines that offer cheap prices include Spirit Airlines from $79 and Southwest from $93 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 United Airlines (81%), Air Canada (80%) and Air New Zealand (80%).

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

    On average you can expect to pay $303 for a flight from Chicago to Kiawah Island. The cheapest flight overall is $128 while the most popular route, (Chicago O'Hare Intl - Charleston) is currently priced at $158.

  • 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 September 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
Allegiant AirCheapest$51Average$93FlexibilityNo cancel feeOn-time88%
DeltaCheapest$98Average$348FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$139Average$384FlexibilityNo cancel feeOn-time71%
Spirit AirlinesCheapest$157Average$203FlexibilityNo cancel feeOn-time65%
SouthwestCheapest$176Average$396FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$230Average$462FlexibilityNo cancel feeOn-time69%

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