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Kiawah Island

$138+ 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 6/8. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — CHS
May 10 — May 171
Sat 5/10
Sat 5/17
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 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 May 5, 2025.

Most accurate provider

Mytrip
3 stars

Most trusted provider

Mytrip
3 stars

Round-trip from

$277
(Mytrip)

One-way from

$138
(JetBlue)

Popular in

December

Cheapest in

August

Average price

$400
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 ($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 May 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 May 5, 2025.

This Mytrip deal was found by Cheapflights users on 5/4. 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.
Wed 6/117:37 amORD - CHS
3 stops27h 28mSpirit Airlines
Sat 6/149:42 amCHS - ORD
2 stops35h 41mSpirit Airlines
Deal found 5/4$277
This American Airlines deal was found by Cheapflights users on 5/4. 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.
Sat 6/214:20 pmORD - CHS
Nonstop2h 09mAmerican Airlines
Sat 6/287:22 amCHS - ORD
Nonstop2h 33mAmerican Airlines
Deal found 5/4$279
This Southwest deal was found by Cheapflights users on 5/4. 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.
Wed 6/111:00 pmMDW - CHS
Nonstop2h 05mSouthwest
Sat 6/147:45 pmCHS - MDW
Nonstop2h 15mSouthwest
Deal found 5/4$279
This United Airlines deal was found by Cheapflights users on 5/4. 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.
Fri 5/306:14 pmORD - CHS
Nonstop2h 18mUnited Airlines
Mon 6/26:30 amCHS - ORD
Nonstop2h 32mUnited Airlines
Deal found 5/4$282
This Delta deal was found by Cheapflights users on 5/4. 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.
Sat 5/244:25 pmORD - CHS
1 stop6h 19mDelta
Wed 5/283:12 pmCHS - ORD
1 stop7h 18mDelta
Deal found 5/4$286
This Delta deal was found by Cheapflights users on 5/4. 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.
Wed 6/116:00 amMDW - CHS
1 stop6h 56mDelta
Sat 6/145:15 amCHS - MDW
1 stop5h 26mDelta
Deal found 5/4$286
This Mytrip deal was found by Cheapflights users on 5/3. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/155:26 pmORD - CHS
1 stop21h 53mMultiple Airlines
Sun 6/89:43 amCHS - ORD
2 stops35h 25mMultiple Airlines
Deal found 5/3$297
This Southwest deal was found by Cheapflights users on 5/4. 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.
Wed 7/21:30 pmORD - CHS
2 stops8h 15mSouthwest
Sat 7/56:30 amCHS - ORD
1 stop6h 20mSouthwest
Deal found 5/4$326
This Mytrip deal was found by Cheapflights users on 5/4. 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.
Thu 5/2911:03 amMDW - CHS
3 stops34h 06mMultiple Airlines
Tue 6/36:00 amCHS - MDW
2 stops34h 37mMultiple Airlines
Deal found 5/4$415

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 May 5, 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

Wed 6/11

7:37 am-12:05 pm

3 stops27h 28m

Charleston

Sat 6/14

9:42 am-8:23 pm

2 stops35h 41m

$277

ChicagoCharleston

ORD - CHS

ORDCHS

Chicago O'Hare Intl

Sat 6/21

4:20 pm-7:29 pm

Nonstop2h 09m

Charleston

Sat 6/28

7:22 am-8:55 am

Nonstop2h 33m

$279

ChicagoCharleston

MDW - CHS

MDWCHS

Chicago Midway

Wed 6/11

1:00 pm-4:05 pm

Nonstop2h 05m

Charleston

Sat 6/14

7:45 pm-9:00 pm

Nonstop2h 15m

$279

ChicagoCharleston

ORD - CHS

ORDCHS

Chicago O'Hare Intl

Fri 5/30

6:14 pm-9:32 pm

Nonstop2h 18m

Charleston

Mon 6/2

6:30 am-8:02 am

Nonstop2h 32m

$282

ChicagoCharleston

ORD - CHS

ORDCHS

Chicago O'Hare Intl

Sat 5/24

5:55 pm-11:44 pm

1 stop4h 49m

Charleston

Tue 5/27

5:35 am-8:29 am

1 stop3h 54m

$286

ChicagoCharleston

MDW - CHS

MDWCHS

Chicago Midway

Wed 6/11

6:00 am-1:56 pm

1 stop6h 56m

Charleston

Sat 6/14

5:15 am-9:41 am

1 stop5h 26m

$286

ChicagoCharleston

ORD - CHS

ORDCHS

Chicago O'Hare Intl

Thu 5/15

5:26 pm-4:19 pm

1 stop21h 53m

Charleston

Sun 6/8

9:43 am-8:08 pm

2 stops35h 25m

$297

ChicagoCharleston

ORD - CHS

ORDCHS

Chicago O'Hare Intl

Wed 7/2

1:30 pm-10:45 pm

2 stops8h 15m

Charleston

Sat 7/5

6:30 am-11:50 am

1 stop6h 20m

$326

ChicagoCharleston

MDW - CHS

MDWCHS

Chicago Midway

Thu 5/29

11:03 am-10:09 pm

3 stops34h 06m

Charleston

Tue 6/3

6:00 am-3:37 pm

2 stops34h 37m

$415

ChicagoCharleston

ORD - CHS

ORDCHS

Chicago O'Hare Intl

Sun 10/26

8:40 am-3:39 pm

1 stop5h 59m

$138

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/5

Showing 1-10 of 23 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 May 2, 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 May 5, 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 Wednesday 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 May 5, 2025.

The most flights from CHI to K1A are scheduled on a Monday (19 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (14 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 May 5, 2025.
Get a feel of what it's like to fly with Alaska Airlines, Southwest 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.
Alaska Airlines
8.0
Very good
9,987 reviews

Overall

8.0

Boarding

8.1

Food

7.1

Entertainment

7.1

Crew

8.5

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Alaska Airlines
8.0
Very good
9,987 reviews
Alaska Airlines
8.0
Very good
9,987 reviews

Overall

8.0

Boarding

8.1

Food

7.1

Entertainment

7.1

Crew

8.5

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Southwest
8.0
Very good
4,292 reviews
Alaska Airlines
8.0
Very good
9,987 reviews

Overall

8.0

Boarding

8.1

Food

7.1

Entertainment

7.1

Crew

8.5

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Delta
8.0
Very good
7,941 reviews
Alaska Airlines
8.0
Very good
9,987 reviews

Overall

8.0

Boarding

8.1

Food

7.1

Entertainment

7.1

Crew

8.5

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Avelo Airlines
7.5
Good
Alaska Airlines
8.0
Very good
9,987 reviews

Overall

8.0

Boarding

8.1

Food

7.1

Entertainment

7.1

Crew

8.5

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
United Airlines
7.4
Good
8,702 reviews
Alaska Airlines
8.0
Very good
9,987 reviews

Overall

8.0

Boarding

8.1

Food

7.1

Entertainment

7.1

Crew

8.5

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

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 $138 on JetBlue. Other airlines that offer cheap prices include Spirit Airlines from $139 and United Airlines from $140 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 (96%), American Airlines (85%) and Envoy Air (84%).

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

    On average you can expect to pay $329 for a flight from Chicago to Kiawah Island. The cheapest flight overall is $139 while the most popular route, (Chicago O'Hare Intl - Charleston) is currently priced at $169.

  • 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.

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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 May 5, 2025.
AirlineCheapestAverageFlexibilityOn-time
Allegiant AirCheapest$76Average$119FlexibilityNo cancel feeOn-time88%
Spirit AirlinesCheapest$101Average$181FlexibilityNo cancel feeOn-time65%
DeltaCheapest$192Average$443FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$226Average$448FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$243Average$388FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$257Average$404FlexibilityNo cancel feeOn-time63%

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