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Kiawah Island

$140+ 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 4/20. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — CHS
mar. 19 — mar. 261
mié. 3/19
mié. 3/26
1 adult, Economy
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The best prices from Chicago to Kiawah Island are usually found in August or September, booked 11 days in advance, depart on a Saturday or Tuesday 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 marzo 14, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$282
(Mytrip)

One-way from

$140
(United Airlines)

Popular in

December

Cheapest in

August

Average price

$412
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. 12% potential increase in price ($58 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 March 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 marzo 14, 2025.

This American Airlines deal was found by Cheapflights users on 3/13. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 4/283:10 pmORD - CHS
1 stop5h 44mAmerican Airlines
mié. 4/3011:55 amCHS - ORD
Nonstop2h 30mAmerican Airlines
Deal found 3/13$282
This Mytrip deal was found by Cheapflights users on 3/13. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 4/225:55 amORD - CHS
1 stop27h 52mSpirit Airlines
dom. 4/2710:25 amCHS - ORD
2 stops22h 39mSpirit Airlines
Deal found 3/13$283
This Southwest deal was found by Cheapflights users on 3/13. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 6/129:50 pmMDW - CHS
Nonstop2h 05mSouthwest
mar. 6/177:15 amCHS - MDW
2 stops7h 05mSouthwest
Deal found 3/13$284
This United Airlines deal was found by Cheapflights users on 3/12. 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.
sáb. 6/216:14 pmORD - CHS
Nonstop2h 18mUnited Airlines
mar. 6/246:30 amCHS - ORD
Nonstop2h 32mUnited Airlines
Deal found 3/12$285
This JetBlue Airways deal was found by Cheapflights users on 3/12. 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 JetBlue Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 8/3111:35 amORD - CHS
1 stop5h 29mJetBlue
jue. 9/411:15 amCHS - ORD
1 stop8h 28mJetBlue
Deal found 3/12$288
This Delta deal was found by Cheapflights users on 3/13. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 4/195:30 amORD - CHS
1 stop4h 57mDelta
mar. 4/222:46 pmCHS - ORD
1 stop5h 14mDelta
Deal found 3/13$294
This Southwest deal was found by Cheapflights users on 3/12. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 4/87:30 amORD - CHS
2 stops8h 50mSouthwest
mar. 4/151:25 pmCHS - ORD
1 stop10h 40mSouthwest
Deal found 3/12$300
This Delta deal was found by Cheapflights users on 3/13. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 5/34:00 pmMDW - CHS
1 stop6h 58mDelta
mar. 5/65:35 amCHS - MDW
1 stop4h 32mDelta
Deal found 3/13$305
This FlightHub deal was found by Cheapflights users on 3/13. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 4/67:00 amORD - CHS
1 stop12h 32mMultiple Airlines
dom. 4/139:05 amCHS - ORD
1 stop22h 58mMultiple Airlines
Deal found 3/13$351
This Mytrip deal was found by Cheapflights users on 3/13. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 4/16:36 pmMDW - CHS
3 stops38h 21mMultiple Airlines
dom. 4/63:56 pmCHS - MDW
2 stops16h 49mMultiple Airlines
Deal found 3/13$616

Find flights from Chicago to Kiawah Island within your budget

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 marzo 14, 2025.

Fly from

Chicago

Fly to

Kiawah Island

Route

Depart

Return

Price

ChicagoCharleston

ORD - CHS

ORDCHS

Chicago O'Hare Intl

lun. 4/28

3:10 pm-9:54 pm

1 stop5h 44m

Charleston

mié. 4/30

11:55 am-1:25 pm

Nonstop2h 30m

$282

ChicagoCharleston

ORD - CHS

ORDCHS

Chicago O'Hare Intl

mar. 4/22

5:55 am-10:47 am

1 stop27h 52m

Charleston

dom. 4/27

10:25 am-8:04 am

2 stops22h 39m

$283

ChicagoCharleston

MDW - CHS

MDWCHS

Chicago Midway

jue. 6/12

9:50 pm-12:55 am

Nonstop2h 05m

Charleston

mar. 6/17

7:15 am-1:20 pm

2 stops7h 05m

$284

ChicagoCharleston

ORD - CHS

ORDCHS

Chicago O'Hare Intl

sáb. 4/19

5:30 am-11:27 am

1 stop4h 57m

Charleston

mar. 4/22

2:46 pm-7:00 pm

1 stop5h 14m

$294

ChicagoCharleston

ORD - CHS

ORDCHS

Chicago O'Hare Intl

mar. 4/8

7:30 am-5:20 pm

2 stops8h 50m

Charleston

mar. 4/15

1:25 pm-11:05 pm

1 stop10h 40m

$300

ChicagoCharleston

ORD - CHS

ORDCHS

Chicago O'Hare Intl

jue. 4/10

8:15 am-9:36 am

3 stops24h 21m

Charleston

lun. 4/14

4:51 pm-12:20 am

3 stops32h 29m

$301

ChicagoCharleston

MDW - CHS

MDWCHS

Chicago Midway

sáb. 5/3

4:00 pm-11:58 pm

1 stop6h 58m

Charleston

mar. 5/6

5:35 am-9:07 am

1 stop4h 32m

$305

ChicagoCharleston

ORD - CHS

ORDCHS

Chicago O'Hare Intl

dom. 4/13

7:10 am-10:31 am

Nonstop2h 21m

Charleston

lun. 4/14

11:40 am-1:15 pm

Nonstop2h 35m

$309

ChicagoCharleston

ORD - CHS

ORDCHS

Chicago O'Hare Intl

sáb. 3/29

8:57 am-6:45 pm

1 stop8h 48m

Charleston

mar. 4/1

7:30 am-12:28 pm

1 stop5h 58m

$336

ChicagoCharleston

MDW - CHS

MDWCHS

Chicago Midway

mar. 4/1

6:36 pm-9:57 am

3 stops38h 21m

Charleston

dom. 4/6

3:56 pm-7:45 am

2 stops16h 49m

$616

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/13

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.

Travel insights for flights from Chicago to Kiawah Island

Get recent, data-driven insights about flights from Chicago to Kiawah Island including ideal travel times, pricing trends, and more.

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 March 7, 2025.

The best time to book flights from Chicago to Kiawah Island is 11 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 marzo 14, 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 Tuesday evenings 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 marzo 14, 2025.

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

Rainfall in Kiawah Island by month

Plan your trip to Kiawah Island by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Kiawah Island ranges from 2.4 - 7.2 inches per month. August is typically the wettest month, when rainfall can reach 7.2 in. November is typically the driest time to visit Kiawah Island when rainfall is around 2.4 in.

Temperature in Kiawah Island by month

Plan your trip to Kiawah Island by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Kiawah Island, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 82.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 48.2 F).

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 marzo 14, 2025.
Get a feel of what it's like to fly with Southwest, Alaska Airlines and Delta from Chicago to Kiawah Island by reading reviews from past customers. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,292 reviews

Entertainment

7.6

Overall

8.1

Crew

8.7

Comfort

8.1

Food

7.1

Boarding

8.2

Reviews

1 / 20

8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

Southwest
8.1
Very good
4,292 reviews
Southwest
8.1
Very good
4,292 reviews

Entertainment

7.6

Overall

8.1

Crew

8.7

Comfort

8.1

Food

7.1

Boarding

8.2

Reviews

1 / 20

8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

Alaska Airlines
8.0
Very good
9,735 reviews
Southwest
8.1
Very good
4,292 reviews

Entertainment

7.6

Overall

8.1

Crew

8.7

Comfort

8.1

Food

7.1

Boarding

8.2

Reviews

1 / 20

8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

Delta
8.0
Very good
7,944 reviews
Southwest
8.1
Very good
4,292 reviews

Entertainment

7.6

Overall

8.1

Crew

8.7

Comfort

8.1

Food

7.1

Boarding

8.2

Reviews

1 / 20

8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

Avelo Airlines
7.5
Good
Southwest
8.1
Very good
4,292 reviews

Entertainment

7.6

Overall

8.1

Crew

8.7

Comfort

8.1

Food

7.1

Boarding

8.2

Reviews

1 / 20

8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

United Airlines
7.4
Good
8,623 reviews
Southwest
8.1
Very good
4,292 reviews

Entertainment

7.6

Overall

8.1

Crew

8.7

Comfort

8.1

Food

7.1

Boarding

8.2

Reviews

1 / 20

8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

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 $140 on United Airlines. Other airlines that offer cheap prices include Southwest from $140 and Spirit Airlines from $141 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 (85%), Air Canada (84%) and Air New Zealand (84%).

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

    On average you can expect to pay $397 for a flight from Chicago to Kiawah Island. The cheapest flight overall is $138 while the most popular route, (Chicago O'Hare Intl - Charleston) is currently priced at $141.

  • 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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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 marzo 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
Allegiant AirCheapest$76Average$132FlexibilityNo cancel feeOn-time88%
Spirit AirlinesCheapest$101Average$179FlexibilityNo cancel feeOn-time65%
DeltaCheapest$133Average$406FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$214Average$443FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$234Average$394FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$257Average$400FlexibilityNo cancel feeOn-time63%
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