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Kiawah Island

$67+ 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 12/11. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — CHS
Dec 13 — Dec 201
Sat 12/13
Sat 12/20
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 68 days in advance, depart on a Tuesday or Monday and return on a Friday

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 November 13, 2025.

This Kiwi.com deal was found by Cheapflights users on 11/11. 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.
Thu 12/47:40 amORD - CHS
2 stops14h 19mMultiple Airlines
Sun 12/711:55 amCHS - ORD
1 stop28h 02mMultiple Airlines
Deal found 11/11$226
This Kiwi.com deal was found by Cheapflights users on 11/11. 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.
Sun 12/73:26 pmORD - CHS
1 stop28h 28mMultiple Airlines
Wed 12/109:13 amCHS - ORD
1 stop21h 52mMultiple Airlines
Deal found 11/11$229
This Mytrip deal was found by Cheapflights users on 11/10. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/57:10 amORD - CHS
1 stop12h 44mSpirit Airlines
Sun 12/79:49 pmCHS - ORD
1 stop14h 19mSpirit Airlines
Deal found 11/10$230
This Kiwi.com deal was found by Cheapflights users on 11/11. 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.
Thu 12/44:38 pmORD - CHS
1 stop17h 22mSpirit Airlines
Sun 12/79:49 pmCHS - ORD
1 stop23h 12mSpirit Airlines
Deal found 11/11$231
This Kiwi.com deal was found by Cheapflights users on 11/11. 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.
Thu 11/206:20 amMDW - CHS
1 stop9h 43mMultiple Airlines
Mon 11/246:13 pmCHS - MDW
1 stop18h 29mMultiple Airlines
Deal found 11/11$232
This Kiwi.com deal was found by Cheapflights users on 11/11. 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.
Thu 12/259:34 amORD - CHS
1 stop26h 36mSpirit Airlines
Mon 1/52:15 pmCHS - ORD
1 stop8h 52mSpirit Airlines
Deal found 11/11$235
This Kiwi.com deal was found by Cheapflights users on 11/11. 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.
Tue 12/97:10 amORD - CHS
2 stops30h 19mMultiple Airlines
Tue 12/162:59 pmCHS - ORD
1 stop7h 49mMultiple Airlines
Deal found 11/11$236
This Kiwi.com deal was found by Cheapflights users on 11/11. 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.
Tue 12/22:01 pmORD - CHS
1 stop16h 25mMultiple Airlines
Wed 12/109:13 amCHS - ORD
1 stop21h 52mMultiple Airlines
Deal found 11/11$237
This Kiwi.com deal was found by Cheapflights users on 11/11. 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.
Tue 12/163:26 pmORD - CHS
2 stops27h 04mMultiple Airlines
Thu 12/182:15 pmCHS - ORD
1 stop19h 16mMultiple Airlines
Deal found 11/11$238
This Kiwi.com deal was found by Cheapflights users on 11/11. 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.
Wed 12/246:12 amMDW - CHS
2 stops15h 24mMultiple Airlines
Thu 1/12:59 pmCHS - MDW
1 stop7h 59mMultiple Airlines
Deal found 11/11$239
This Cheapflightsfares deal was found by Cheapflights users on 11/12. 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.
Thu 11/2010:12 amORD - CHS
1 stop10h 53mSpirit Airlines
Mon 11/248:31 amCHS - ORD
1 stop5h 25mSpirit Airlines
Deal found 11/12$242
This Mytrip deal was found by Cheapflights users on 11/11. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/123:26 pmORD - CHS
2 stops18h 34mSpirit Airlines
Mon 12/1511:55 amCHS - ORD
3 stops33h 06mSpirit Airlines
Deal found 11/11$244

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 November 13, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$226
(Kiwi.com)

One-way from

$67
(Cheapflightsfares)

Popular in

January

Cheapest in

August

Average price

$419
Provider with most accurate pricing for Chicago (CHI)-Charleston flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Charleston flights.
Search Deals
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. 5% potential increase in price ($23 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($5 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2025
Search Deals

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 November 13, 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

Tue 12/2

7:00 am-1:48 pm

1 stop5h 48m

Charleston

Mon 12/8

10:51 am-7:43 pm

1 stop9h 52m

$286

ChicagoCharleston

ORD - CHS

ORDCHS

Chicago O'Hare Intl

Sat 1/31

10:36 am-2:02 pm

Nonstop2h 26m

Charleston

Sat 2/7

10:30 am-11:59 am

Nonstop2h 29m

$299

ChicagoCharleston

MDW - CHS

MDWCHS

Chicago Midway

Wed 12/24

3:29 pm-9:50 pm

1 stop5h 21m

Charleston

Wed 12/31

6:00 am-9:05 am

1 stop4h 05m

$299

ChicagoCharleston

MDW - CHS

MDWCHS

Chicago Midway

Wed 12/24

3:29 pm-8:39 pm

1 stop4h 10m

Charleston

Thu 1/1

6:00 am-9:05 am

1 stop4h 05m

$299

ChicagoCharleston

ORD - CHS

ORDCHS

Chicago O'Hare Intl

Tue 12/2

2:03 pm-9:06 pm

1 stop6h 03m

Charleston

Sat 12/6

1:45 pm-3:21 pm

Nonstop2h 36m

$309

ChicagoCharleston

ORD - CHS

ORDCHS

Chicago O'Hare Intl

Sat 12/6

7:00 am-3:10 pm

1 stop7h 10m

Charleston

Wed 12/10

4:38 pm-6:10 pm

Nonstop2h 32m

$309

ChicagoCharleston

MDW - CHS

MDWCHS

Chicago Midway

Thu 1/1

6:35 am-12:25 pm

1 stop4h 50m

Charleston

Mon 1/5

7:15 pm-8:30 pm

Nonstop2h 15m

$317

ChicagoCharleston

ORD - CHS

ORDCHS

Chicago O'Hare Intl

Tue 1/13

7:05 am-12:07 pm

1 stop4h 02m

Charleston

Tue 1/27

11:45 am-4:56 pm

1 stop6h 11m

$319

ChicagoCharleston

ORD - CHS

ORDCHS

Chicago O'Hare Intl

Thu 1/1

12:59 pm-4:17 pm

Nonstop2h 18m

Charleston

Sat 1/3

6:25 am-8:03 am

Nonstop2h 38m

$324

ChicagoCharleston

ORD - CHS

ORDCHS

Chicago O'Hare Intl

Sun 2/8

10:36 am-2:02 pm

Nonstop2h 26m

Charleston

Sun 2/15

6:00 am-7:35 am

Nonstop2h 35m

$324

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/10

Showing 1-10 of 43 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 November 7, 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, 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 December is currently the most expensive (average of $256). 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 November 13, 2025.

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 at noon, which can drop the price by up to 28% versus a flight in the afternoon.

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 Tuesday mornings when fares are most often at their lowest. Thursday 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 November 13, 2025.

The most flights from CHI to K1A are scheduled on a Thursday (21 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (12 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 November 13, 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

Food

7.0

Overall

8.0

Boarding

8.1

Comfort

8.0

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

Food

7.0

Overall

8.0

Boarding

8.1

Comfort

8.0

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
7.9
Good
8,007 reviews
Southwest
8.0
Very good
4,242 reviews

Food

7.0

Overall

8.0

Boarding

8.1

Comfort

8.0

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
9,017 reviews
Southwest
8.0
Very good
4,242 reviews

Food

7.0

Overall

8.0

Boarding

8.1

Comfort

8.0

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
11,051 reviews
Southwest
8.0
Very good
4,242 reviews

Food

7.0

Overall

8.0

Boarding

8.1

Comfort

8.0

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
8,139 reviews
Southwest
8.0
Very good
4,242 reviews

Food

7.0

Overall

8.0

Boarding

8.1

Comfort

8.0

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 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 most reliable airlines from Chicago to Kiawah Island?

    The top 3 most reliable airlines when flying from Chicago to Kiawah Island are Republic Airways (89%), Qatar Airways (88%) and Alaska Airlines (84%).

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

    On average you can expect to pay $438 for a flight from Chicago to Kiawah Island. The cheapest flight overall is $87 while the most popular route, (Chicago O'Hare Intl - Charleston) is currently priced at $160.

  • 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 December is currently the most expensive (average of $256). 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 November 13, 2025.
AirlineCheapestAverageFlexibilityOn-time
Allegiant AirCheapest$51Average$93FlexibilityNo cancel feeOn-time88%
DeltaCheapest$98Average$374FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$139Average$384FlexibilityNo cancel feeOn-time71%
Spirit AirlinesCheapest$157Average$203FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$232Average$455FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$245Average$367FlexibilityNo cancel feeOn-time63%

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