$116 Find Cheap Flights from Chicago to Kiawah Island

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 5/27. 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
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights from Chicago to Kiawah Island

Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 24% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Free to useThere are no hidden charges or fees.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Everything you should know

Cheapest round-trip
$265
Typical prices: $468-$342
United Airlines
Mon 5/25Mon 6/1
ORD - CHS • Non-stop
Cheapest one-way
$116
Typical prices: $177-$332
Multiple Airlines
Wed 5/27
ORD - CHS • 1 stop
Arrival airport
You can't fly directly to Kiawah Island. It is served by Charleston (CHS), located 19.9 miles from Kiawah Island.
FAQs
FAQs
FAQs
FAQs
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Kiawah Island!
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

Mon, May 25 - Mon, Jun 1
United Airlines Logo
7:00 am - 10:23 am
ORD
-
CHS
2h 23mnonstop
United Airlines Logo
6:00 am - 7:33 am
CHS
-
ORD
2h 33mnonstop
$265United Airlines
Sat, May 16 - Wed, May 20
Southwest Logo
3:30 pm - 6:35 pm
MDW
-
CHS
2h 05mnonstop
Southwest Logo
7:15 am - 8:30 am
CHS
-
MDW
2h 15mnonstop
$265Southwest
Thu, May 28 - Mon, Jun 1
American Airlines Logo
7:41 pm - 11:00 pm
ORD
-
CHS
2h 19mnonstop
American Airlines Logo
7:51 pm - 9:44 pm
CHS
-
ORD
2h 53mnonstop
$267American Airlines
Tue, May 26 - Tue, Jun 2
Southwest Logo
12:50 pm - 8:25 pm
MDW
-
CHS
6h 35m
2 stops
Southwest Logo
1:15 pm - 8:10 pm
CHS
-
MDW
7h 55m
2 stops
$267Southwest
Mon, Jun 1 - Tue, Jun 9
Multiple Airlines Logo
5:11 pm - 9:58 am
ORD
-
CHS
15h 47m
1 stop
Multiple Airlines Logo
8:00 am - 8:03 am
CHS
-
ORD
25h 03m
2 stops
$269Multiple Airlines
Sat, May 23 - Wed, Jun 3
Delta Logo
3:00 pm - 9:52 pm
ORD
-
CHS
5h 52m
1 stop
Delta Logo
10:43 am - 4:56 pm
CHS
-
ORD
7h 13m
1 stop
$271Delta
Wed, May 27 - Mon, Jun 1
Delta Logo
10:59 am - 3:49 pm
MDW
-
CHS
3h 50m
1 stop
Delta Logo
7:05 am - 12:42 pm
CHS
-
MDW
6h 37m
1 stop
$271Delta
Thu, May 14 - Tue, May 19
Multiple Airlines Logo
3:44 pm - 8:48 am
ORD
-
CHS
40h 04m
2 stops
Multiple Airlines Logo
3:13 pm - 11:13 pm
CHS
-
ORD
9h 00m
1 stop
$272Multiple Airlines
Thu, May 28 - Sat, May 30
United Airlines Logo
7:00 am - 10:23 am
ORD
-
CHS
2h 23mnonstop
United Airlines Logo
10:00 am - 2:40 pm
CHS
-
ORD
5h 40m
1 stop
$275United Airlines
Thu, May 28 - Mon, Jun 1
American Airlines Logo
4:45 pm - 10:06 pm
ORD
-
CHS
4h 21m
1 stop
American Airlines Logo
7:51 pm - 9:44 pm
CHS
-
ORD
2h 53mnonstop
$277American Airlines
Useful Info

Good to know

Low seasonFebruary
Cheapest flight$116
Best time to beat the crowds with an average 3% drop in price.
Most popular time to fly with an average 1% 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?

    36 direct flights run between Chicago and Kiawah Island on a daily basis. On average, there are about 258 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 72 hours, the cheapest one-way ticket between Chicago and Kiawah Island found on KAYAK was with United Airlines for $124. Spirit Airlines offered a round-trip connection from $109 and Delta from $149.

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 60 days before departure, on average.
  • Book at least 1 week 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.
8.0
SouthwestOverall score based on 4314 reviews
7.0Food
8.0Comfort
7.5Entertainment
8.6Crew
8.1Boarding
Airline reviews

The entire experience from boarding to landing was amazing! The crew were very friendly. Will definitely be back.

10.0 Excellentlarry, Apr 2026
LGB - PHX
Read more Southwest reviews

The entire experience from boarding to landing was amazing! The crew were very friendly. Will definitely be back.

no service at all due to turbulence. they should've at least given us snacks, there were only 10 people on the entire flight.

First time I've had to use the disabled accommodations. And I could not have had a better experience with Southwest, i was having trouble getting from one terminal to another due to my heart failure. And the next thing I know a Southwest agent had made sure. I had a wheelchair at all my flights. Can't thank them enough.

Delayed flight, lack of information, boarding process is a mess as is the carryon luggage causing issues when leaving the plane….just a poor experience.

Comfortable. Easy. No problems. Just wish they had gf options for snacks.

The crew was very kind and made going to Hawaii relaxing and fun to look forward to! Thank you Southwest for a pleasant flight!

This leg was much better, but we did have to have a 3 hour lay o er after coming from a very exhausting hiccup with our flight from BNA to Den

We waited in the airplane for over 45 min for a southwest employee to make the flight. This cause over half the plane to miss their connecting flight in Denver. When we confronted the desk upon arrival, they told us the only flight they had was the next day leaving at 8:50 pm!!! Or they offered to get us to Burbank or LA, but after that we were on our own to get back to Santa Barbara. I paid for a flight from sba to bna bna to sba. My re entry into mom mode has been 💯 rough because of southwest mistake with my flight. And now I’m leaving to Reno tomorrow for a vballl tournament and just discovered that my leg in Vegas has me and my 3 kids on a stand by flight even though I had booked these ticket last year November!! Do better southwest!

Southwest is kind of a slum airline. It’s gotten more expensive over the years for less and less service. I am a Southwest Chase Visa card holder and was forced to choose a seat in the 26th row in the middle seat. However my wife who is a rewards member but doesn’t hold a card or anything else, gets randomly assigned a normally paid seat in row 6! How does that work?

For the first time in a long time, the Wi-Fi actually worked the entire flight! The flight crew was amazing as usual.

The agent at check in and at the gate were less than thrilled to be at work. I'm not a fan of Kayak's placement on the plane. I got put in the middle seat and none of my preferences were used.

In ATL they have two sets of departure screens. Follow what is on your airline's departure board - the ATL Airport Authority departure board had completely incorrect details about the gate assignment for my flight, which would have made me miss boarding.

Flight was delayed it was hot while sitting on the plane, one engine was working on the plane until they had to do some jimmy rigging down the runway in order for the other engine to charge up. It was ridiculous

The flight was very good and the staff was very friendly and helpful!

The only thing I would say is we tried to get on a standby earlier flight, but with our fair we couldn’t. That seems senseless to leave with open seats..

Very easy to use and convenient, you can perform any action within the same portal

In a world of delays, Delta was on time both ways! Boarding was fast and efficient. Staff was friendly. AND wifi worked.

WiFi didn’t work. Flight delayed 3 hours Crew members were illiterate Seat lean back did not work.

Flight was delayed, we could have been notified earlier and in a consistent manner. App was not refreshing for another passenger to get the latest flight status. We could have stayed and waited at the hotel instead of waiting at the airport had we known the flight was going to delayed for more than 5 hours. The toilet is too tight, and needs to be cleaned more frequently (every hour). The entertainment screen froze, the touch screen not responding to touch. We were upgraded to comfort, it is more comfortable than regular economy seats.

This wasn't my experience with Delta. It was just the Pegasus flight. Seats were very hard. Staff was kinda rough. Not very nice. Charged me for snacks. For a 4 hour flight I would've expected more.

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.

Terrible, if possible won't be flying again anytime soon!

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.

The gate got changed several times and the flight was delayed over an hour. Awful experience

American continues to decline in their customer service and its beyond disappointing.

It was an older plane. First Class was not especially roomy or comfortable. It was a short flight so there were no meal but they did offer mixed nuts which used to be normal but now is rare. Crew member was very polite and professional.

Flight to Tampa was delayed taking off due to plane arriving late but no other issues

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

Complete your trip to Kiawah Island with a hotel stay or car rental