$103 Find Cheap Flights from Chicago to Kiawah Island - Compare and Save

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Kiawah Island departing on 9/8. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
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Everything you should know

Cheapest round-trip
$287
Typical prices: $433-$323
Southwest
Wed 7/15Tue 7/21
MDW - CHS • 2 stops
Cheapest non-stop
$289
Typical prices: $454-$333
American Airlines
Tue 6/30Sat 7/11
ORD - CHS • Non-stop
Arrival airport
You can't fly directly to Kiawah Island. It is served by Charleston (CHS), located 19.9 miles from Kiawah Island.
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Flight Deals
Useful Info
Flight Deals

Cheap Flights from Chicago to Kiawah Island (CHI-CHS)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to Kiawah Island that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Chicago to Kiawah Island

Wed, Jul 15 - Tue, Jul 21
Southwest Logo
11:25 am - 8:30 pm
MDW
-
CHS
8h 05m
2 stops
Southwest Logo
10:45 am - 6:15 pm
CHS
-
MDW
8h 30m
2 stops
$287Southwest
Thu, Sep 17 - Mon, Sep 21
American Airlines Logo
2:56 pm - 10:08 pm
ORD
-
CHS
6h 12m
1 stop
American Airlines Logo
7:41 pm - 11:59 pm
CHS
-
ORD
5h 18m
1 stop
$289American Airlines
Thu, Sep 24 - Mon, Sep 28
Delta Logo
10:48 am - 6:08 pm
MDW
-
CHS
6h 20m
1 stop
Delta Logo
5:25 am - 9:53 am
CHS
-
MDW
5h 28m
1 stop
$289Delta
Fri, Sep 18 - Thu, Sep 24
Delta Logo
6:40 am - 1:04 pm
ORD
-
CHS
5h 24m
1 stop
Delta Logo
7:10 am - 10:37 am
CHS
-
ORD
4h 27m
1 stop
$290Delta
Thu, Aug 6 - Mon, Aug 10
Delta Logo
12:46 pm - 8:44 pm
MDW
-
CHS
6h 58m
1 stop
Delta Logo
11:25 am - 4:15 pm
CHS
-
MDW
5h 50m
1 stop
$290Delta
Wed, Oct 7 - Sat, Oct 10
American Airlines Logo
8:46 pm - 12:15 am
ORD
-
CHS
2h 29mnonstop
American Airlines Logo
6:36 pm - 9:26 pm
CHS
-
ORD
3h 50m
1 stop
$291American Airlines
Thu, Sep 17 - Wed, Sep 23
Delta Logo
1:00 pm - 6:08 pm
MDW
-
CHS
4h 08m
1 stop
Delta Logo
6:40 am - 9:53 am
CHS
-
MDW
4h 13m
1 stop
$292Delta
Sat, Jul 25 - Wed, Jul 29
Southwest Logo
8:00 am - 4:15 pm
MDW
-
CHS
7h 15m
2 stops
Southwest Logo
6:10 am - 7:20 am
CHS
-
MDW
2h 10mnonstop
$294Southwest
Sat, Jul 11 - Tue, Jul 14
United Airlines Logo
6:25 pm - 9:48 pm
ORD
-
CHS
2h 23mnonstop
United Airlines Logo
6:00 am - 7:33 am
CHS
-
ORD
2h 33mnonstop
$297United Airlines
Tue, Jun 30 - Sat, Jul 11
United Airlines Logo
6:00 am - 2:27 pm
ORD
-
CHS
7h 27m
1 stop
United Airlines Logo
3:08 pm - 4:54 pm
CHS
-
ORD
2h 46mnonstop
$299United Airlines
Useful Info

Good to know

Low seasonFebruary
Cheapest flight$103
Best time to beat the crowds with an average 3% drop in price.
Most popular time to fly with an average 3% increase in price.
Flight from Chicago O'Hare Airport to Charleston

When to book flights from Chicago to Kiawah Island

Are your dates flexible? Find out the best times to travel from Chicago to Kiawah Island based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price

FAQs for booking flights from Chicago to Kiawah Island

  • Which airports will I be using when flying from Chicago to Kiawah Island?

    When flying out of Chicago you’ll be using one of these airports: Chicago Midway or Chicago O'Hare Intl. Kiawah Island does not have its own airport so you’ll be flying into nearby Charleston airport, which is 19.9 mi away.

  • How long does a flight from Chicago to Kiawah Island take?

    Direct flights cover the 746 miles separating Chicago and Kiawah Island in about 2h 05m.

  • How many flights are there between Chicago and Kiawah Island?

    24 direct flights run between Chicago and Kiawah Island on a daily basis. On average, there are about 173 departures each week.

  • What’s the cheapest day of the week to fly between Chicago and Kiawah Island?

    Consider leaving on a Monday and avoid Wednesdays if you are looking for the best rates. For your return to Chicago, you’ll find the best rates on Thursdays and the most expensive ones on Sundays.

  • How does KAYAK find such low prices on flights from Chicago to Kiawah Island?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago to Kiawah Island.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago to Kiawah Island?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Kiawah Island from Chicago is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago to Kiawah Island?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Kiawah Island with an airline and back to Chicago with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago to Kiawah Island?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Kiawah Island from Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • Which airlines provide the cheapest flights from Chicago to Kiawah Island?

    In the last 5 days, the cheapest one-way ticket between Chicago and Kiawah Island found on KAYAK was with United Airlines for $124. Delta offered a round-trip connection from $149 and Southwest from $153.

Top tips for finding cheap flights from Chicago to Kiawah Island

  • There is no airport in Kiawah Island. Instead, you’ll be flying into Charleston Municipal Airport when flying between Chicago and Kiawah Island.
  • The cheapest flight from Chicago to Kiawah Island was found 54 days before departure, on average.
  • Book at least 3 weeks before departure in order to get a below-average price.
  • High season is considered to be February, March and April. The cheapest month to fly is August.

Reviews of the top 4 airlines serving Chicago to Kiawah Island

 
Need help choosing which airline to fly with from Chicago to Kiawah Island? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.9
SouthwestOverall score based on 4235 reviews
8.0Comfort
8.6Crew
8.1Boarding
7.5Entertainment
7.0Food
Airline reviews

Flight was delayed over 3 hours. Planes were dirty. Staff indifferent. And they serve vegan pretzels as snacks.

2.0 MediocreMatthew, Jun 2026
CVG - MDW
Read more Southwest reviews

Flight was delayed over 3 hours. Planes were dirty. Staff indifferent. And they serve vegan pretzels as snacks.

It was great. The gate staff were very helpful in Portland when my son forgot his rolling bag and had to go back to get it just in time to make it on the plane. We really appreciate that. Great job!

Airline is not very senior friendly. Flights are late, forcing us to run to the connecting flight. Food is awful. Wish they would go back to pretzels and peanuts. During flight, pressurization isn’t quite right and all of our ears get plugged. Everything is nickel and dime, charging for boarding, seat selection and legroom. While a screen at the desk in the gate area says check your roll on bag now for free due to space limitation, the employee at the desk will not check the bag without a $100 fee. Insane.

Kayak could’ve posted the correct gate number. Almost missed my flight.

Slow boarding, limited food and drink portions. Bad delays and turbulence

there were two flight attendants that were up front...that were the best! They get KUDOs for making my trip only fantastic. Tell them Jeff said that!

OKay. I sat in the back of the plane and it was really loud between babies and little kids, and adults who.like to talk a lot and loudly most of the flight.

Flight coming out of Buffalo was delayed, so we had to be rescheduled on another flight from Baltimore to Phoenix which means we had a long layover and got home 3.5 hours late. Shuttle to parking stopped at 10pm, so we had to pay for an Uber to the parking lot and got charged an extra day of parking since it was after midnight. Not the best experience. Long day!

Was fine, delayed and feels like southwest is always late

I don't know why flying out of Sarasota requires two plane changes.

Five hour delays every hour, I wish it were all at once

Flight delayed four separate times. I’m now one hour hours late to landing.

worst flight ever from Delta, it got delayed and kept on delaying..

Should never have had to go to Detroit from Orlando back to Tennessee!

Got rerouted from a straight flight from Orlando to Atlanta to Knoxville to a flight from Orlando to Detroit to Knoxville! Seriously!! Flight delay out of Detroit! Long day for what should have been a pretty easy travel day!

Two delays on two separate planes with parts they could not easily find and replace.

Checkin was good, fllight ws good. Onlly complaint is lack of foot on 6 hour flight from Seattle to Boston. Snacks were flimsy - chips and cookies. could have offered something more substantial for such a long flight. I know you can buy food in airport but for the price you pay for a ticket, they should step up for the passengers.

Only beverages were offered to first class and I thought the flight attendant could have also served the Delta Comfort as well instead of sitting down and staring at her phone and walking past all of us to the back of the plane to charge her phone more. There was a complete lack of turbulence and was safe enough for flights attendant to walk around in the front of the plane, collect trash and serve a few people water and turn off the seat belt light. Also didn’t enforce people putting their seats into the upright position and allowed two passengers to remain reclined during landing. They seemed out to lunch completely. Usually my experience on Delta is much better.

Long story short, it was one of the better flight experiences I've had in some time when compared with other airlines.

Flight was great! This flight from Atlanta was even better than when I paid for Comfort from SNA to Atlanta.

Boarded early; and arrived home 40 mins early. After a long flight, it’s nice to be back home early. These flights have no amenities; no snacks. So need to bring your own

A long delay. Don't travel late in the day.

Super friendly with lots of drink options an entertainment. Friendly crew.

The crew was great. Very friendly and responsive. The plane was old, small and tight. We ran out of overhead space and I had to check. Middle seat was particularly tight.

Several missed and almost missed connections. It felt like everything was being patched together last minute without enough resources and it ended up being an extremely stressful experience that basically ruined our weekend on the west coast. What a waste.

Crew was friendly. Seats are too narrow, particularly when a big person is in the adjacent seat, but I understand this is due to smaller planes usually flight into Lincoln. I have experienced several flight delays going out and coming into Lincoln airport, I say maybe 50% or higher of the flights I've taken out of this airport have been delayed.

Great flight. Boarded efficiently. Arrived early at CLT. There was no in flight entertainment on this aircraft. Great crew.

The seat was comfortable. There was a lot of turbulence. If it weren't for that,it would have been okay.

Poor communication, flight was delayed for preventable reasons. I missed my connection.

No meal service to the back of the plane as it started late or was too slow to get it out before it was time to land.

I’ve got 31F seat and window seat . My 2 co passengers was AA crew members and they were very rude attitude and when I was going to use bathroom their gestures was very different and awkward and the guy beside me completely occupied the hand rest and I was really uncomfortable

It was so much better than expected, Ohare is not such a pleasant experience but American Airlines with the new, clean aeroplane and free Wi-Fi was outstanding and the crew so pleasant and helpful.

It wa sort of on time; the cab was left with some trash

American Airlines II: Delay Boogaloo. Multiple gate changes, delays, boarded and then MORE delays. I hate to say this won’t matter, but posting stuff about major corporations in 2026 is a post-modern “scream into the void.” Was multiple hours late coming home, so there you go.

The airplane was an old model, the overhead didn’t have enough room for people’s items and made boarding and boarding disappointing and stressful. Crew allowed passengers to bring more than the permitted baggage sizes.

Original flight was on time, then late, then changed gates...4 times. Once our newest plane came in, it was fine.

I almost missed my flight and they helped me out enormously

Delays experienced in boarding/take off due to incoming plane delayed. However, the boarding time/depart time in the app was significantly delayed in providing these updates. Usually not updated until an hour after we should have already boarded. Poorly managed.

Moved to earlier flight which unexpectedly had maintenance issues initially indicated as quick fix to ultimately plane changes. Moved back to original flight, also delayed. In all cases customer updates and communication very unclear, no updates on drivers for delays.

Typical AA - late by 90+ mn. Gate changed twice... Changed the departure time 6 times No explanation, no communication on reasons for delay I travel with AA twice a year... and it is consistently very poor.. I will continue to use AA only when i have to.

Everything you need to know for your flight from Chicago to Kiawah Island

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