$71 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 9/17. 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.
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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

Thu, Oct 2 - Mon, Oct 6
Spirit Airlines Logo
5:05 am - 9:05 amORD-CHS
27h 00m1 stop
Spirit Airlines Logo
10:31 am - 3:50 pmCHS-ORD
6h 19m1 stop
$194Spirit Airlines
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Wed, Sep 10 - Fri, Sep 19
Spirit Airlines Logo
6:44 pm - 10:45 amORD-CHS
15h 01m1 stop
Spirit Airlines Logo
6:08 pm - 5:39 pmCHS-ORD
24h 31m2 stops
$195Spirit Airlines
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Thu, Nov 13 - Sun, Nov 16
 Logo
9:23 am - 5:47 pmORD-CHS
7h 24m1 stop
 Logo
5:40 pm - 11:42 pmCHS-ORD
7h 02m1 stop
Thu, Nov 6 - Sun, Nov 9
Frontier Logo
9:23 am - 5:47 pmORD-CHS
7h 24m1 stop
Frontier Logo
7:02 pm - 12:59 amCHS-ORD
6h 57m1 stop
$198Frontier
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Thu, Sep 11 - Mon, Sep 15
 Logo
12:53 pm - 9:05 amORD-CHS
19h 12m2 stops
 Logo
10:10 am - 10:48 pmCHS-ORD
13h 38m1 stop
Thu, Sep 11 - Thu, Sep 18
Frontier Logo
8:15 am - 2:31 pmMDW-CHS
5h 16m1 stop
Frontier Logo
3:26 pm - 7:11 amCHS-MDW
16h 45m1 stop
$227Frontier
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Tue, Sep 16 - Tue, Sep 23
Southwest Logo
6:05 pm - 9:15 pmMDW-CHS
2h 10mnonstop
Southwest Logo
6:35 am - 7:40 amCHS-MDW
2h 05mnonstop
$257Southwest
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Thu, Sep 18 - Tue, Sep 23
Southwest Logo
7:35 pm - 10:40 pmMDW-CHS
2h 05mnonstop
Southwest Logo
6:35 am - 7:40 amCHS-MDW
2h 05mnonstop
$264Southwest
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Tue, Nov 11 - Tue, Nov 18
Delta Logo
1:05 pm - 6:55 pmMDW-CHS
4h 50m1 stop
Delta Logo
9:10 am - 11:55 amCHS-MDW
3h 45m1 stop
$277Delta
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Sat, Aug 30 - Tue, Sep 9
Delta Logo
6:17 pm - 11:55 pmMDW-CHS
4h 38m1 stop
Delta Logo
7:10 am - 12:28 pmCHS-MDW
6h 18m1 stop
$288Delta
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Good to know

Low seasonJanuary
Cheapest flight$71
Best time to beat the crowds but there is an average 12% increase in price.
Most popular time to fly with an average 9% 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 5h 16m.

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

    19 direct flights run between Chicago and Kiawah Island on a daily basis. On average, there are about 136 departures each week.

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

    Consider leaving on a Thursday and avoid Tuesdays 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 Mondays.

  • 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 Spirit Airlines for $71. Spirit Airlines offered a round-trip connection from $194 and Frontier from $198.

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 85 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 November, December and January. The cheapest month to fly is August.

Reviews of the top 5 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 4246 reviews
8.0Comfort
7.5Entertainment
8.6Crew
7.0Food
8.1Boarding
Airline reviews

Near 4 hour flight with only 1 service. Had to use call button to request water. Internet and power not working until into flight. Internet would stop working during flight.

6.0 GoodDavid, Aug 2025MCO - DEN
Read more Southwest reviews

Near 4 hour flight with only 1 service. Had to use call button to request water. Internet and power not working until into flight. Internet would stop working during flight.

Southwest's seats are the least comfortable I have ever sat in.

The cabin was quiet for the redeye flight. The area was clean. The staff was great. The 787 Max was in good condition. Drawbacks were that the seat widths were tight for some passengers. The seat padding was at best average and for a long flight uncomfortable.

Southwest like most American domestic airlines, is a mediocre airline. But it is among the cheapest. Oh well.

My flight was delayed 50 minutes and we were rushed to board to then sit for 15 minutes until the pilot arrived. Unacceptable since we could have waited to board. Also the delayed flight was updated AFTER we boarded to more than the 10 minutes as originally stated.

Other than a bit of a delay, everything was good. Again, the boarding process and picking seats is the only thing I don't enjoy.

If we are going to have to pay for luggage, make it easier to do. Put something on the app during check-in so I don't need to do it at the kiosk. I've done it twice recently and I ended up having to pay at the desk because something went wrong at the kiosk in Tampa.

Better and more food and drinks. Put msnbc and free speech tv on the news channel selection list.

southwest just starting charging for luggage. hadnt realized it until it was too late. now out $70 when i couldve bought a carry on if i wouldve known. free bags was one of the only reasons i chose southwest over another airline (the other being no assigned seats, which is apparently also being changed). stupid business decision. wont be flying southwest anymore.

The quality of Southwest Airlines continues to degrade each time I fly with them. If it were not for the free luggage, I would probably choose another airline. Their prices are a little bit competitive, but way too high for the quality of the service. Southwest is not unique in this way. Domestic flight in the United States of America has continued to be a lower and lower quality product. Very sad when you compare the quality of domestic airlines to that of many international airlines around the world.

Three seats in first class were broken and while they were able to still acommodate us it was looking very touch and go and they had others they could not acommodate

Mechanic delay in addition to a 2 hour change in takeoff time was frustrating.

Delayed due to thunderstorms and no in-flight service due to rough weather — both of which are out of Delta’s control. Flight was good overall.

The flight attendants in SLC were rude. I arrived 40 minutes early to gate. Ticket said I needed check in for seat assignments and tried check in and attendants said they weren’t doing it. And proceeded to never call me to give me a ticket so when time to board I received the very last seat. Please relay to employees to do their job better..,

On this flight I felt the food offering was not as complete as on previous flights. The tomato salad was a bit off and there was nothing additional such a bread or butter. The breakfast was only one option, so you either ate what they had or ate nothing. The crew was efficient, but most seemed frustrated throughout the flight. The flight arrived early and was obstacle-free, so I’m overall quite happy, but the shine in the rest of the experience just wasn’t there.

The seats got pretty uncomfortable pretty fast. The armrests are bigger than on other planes, so I had less room in the actual seat. My butt hurt by the end of the flight. :/ comfort was the primary issue. The crew were fantastic!

I believe that a four-hour trip should have a meal. Delta had none.

Great flight with Delta! Boarding was quick and easy, the amenities were solid, and the plane was in great shape. The flight attendants had a fun, lively energy while staying professional. All in all, a smooth trip — even managed to catch up on some rest. Thanks, Delta!

I was uncomfortably cold on the plane. Other than that it was uneventful and therefore as enjoyable as a plane ride can be.

There was supposed to be a meal served, but there wasn’t and the major toilet was out of order

Excellent flight. Boarding was efficient and departure was on time. Smooth flight with on time arrival. Deplaning was also efficient.

It was delayed instead of departing at 9:20pm, we departed at 11pm… putting us in Columbus after 2am! It was awful. Had I known about the delay, I could have spent some time in the United Lounge… I was starving because I started my journey in Budapest… so I was exhausted and hungry. Plus I had to make new arrangements to be picked up at the airport in Columbus, instead of midnight it was 2:30 am after getting luggage and out of airport. Not feasible. I would have just stayed in Chicago for the night and gotten a morning flight.

It was great, I’m very grateful for the pilots and crew flight attendants for everything.

Evidently, my seat had the only broken TV. I couldn’t plug it in, get it to come on, or watch anything, and of course, no one could fix it while we were on the plane. The service was good and the boarding was quick

I was charged for my daughters bag when I am supposed to receive two free checked bags with my United Explorer card.

The schedule to Moline changed 5 times. The gate changed 6 times. That is a pathetic way to run an airline. No wonder that no one in our company flies on United Express to or from Moline. Changes happen most of the time. I learned my lesson on this trip…never again!

Flight was great. Efficient boarding. Short flight. Early arrival. Friendly flight crew. The entertainment system did not work well. Could not access it until the aircraft reached 10K feet or more. Lots of glitches.

A bit rush for transit. Food and entertainment are not available

Smooth boarding process. Early departure, smooth flight, early arrival. The entertainment package has very good recent movie options. The flight crew were friendly and professional.

My flight was scheduled for about 6:05 departure. There were 11 gate changes from 4-7pm and the flight was 3 hours delayed due to operational issues. The plane taxied around the airport for about half an hour before stopping to be de-iced. It would have been nice if we were alerted of the plan to de-ice prior to the 30 minute drive around the airport. The flight attendant was friendly, which was the only redeeming thing about this flight. As a former flight attendant for United, I was extremely disappointed.

3 hour weather delay followed by 1 hour (and counting) maintenance delay. UGH!

After we'd boarded , they canceled the flight. The crew didn't even know , we just all received text messages. Then after they deplaned us , AA was just like "too bad, go F your self, we sure ain't gonna help you"

After a two hour delay, my flight was CANCELLED! No pilot available. Such BS.

Amazing food, great staff, with one noticable detail missing ...but no seat entertainment in any of aircraft ...I am not a fan

I wish American Airlines would change the airline industry by loading the plane back to front instead of front to back. Planes would board so much more smoothly and quickly.

I have long legs, my foot was out in the aisle and when a flight attendant came walking by and I didn't notice, instead of saying "excuse me" or anything like that, she kicked my foot. Extremely rude

Excellent! The gate agents were kind enough to rebook me on an earlier flight saving me from a 6 hour layover. Even my luggage made it despite the fact that the connection was technically too narrow. The flight itself was very comfortable, roomy, and clean. Plenty of space for my carryon items with plugs to charge my phone. After a long international flight of 14 hours, this was an excellent way to end my travels!

Great experience. Flight boarded easily. Departed early. Smooth flight. Great arrival in DC--almost no taxing! Almost direct to gate from runway. Crew was terrific. Same cookies and beverages in main cabin. I did not use the entertainment system on this flight.

Most of the delay was due to weather which is not what was at issue here. One delay was due to a missing flashlight and in the end the flashlight was actually found on the plane. The entertainment system is very limited. Live TV options offer only a few channels that are not very appealing. Boarding and deplaning are always difficult. It just takes too much time to get on and off the plane. On the plus side, I missed my connecting flight, but was easily able to book a later flight from the app while enroute.

You were more on time than United. I'm so over united delays.

After 2 hrs the flight was canceled. The next flight wasn’t until 4 days away! They wouldn’t book us with other airlines. We ended up driving 15 hrs to get home

The flight was on time, boarding was efficient, staff was nice. Seats seem to have been upgraded on this model and were clean and tidy. I did not purchase in flight snacks.

It was very bad it got delayed by 2 hours.Never going to travel with spirit airlines in future.

The flight times got delayed multiple times due to weather which is understandable, but later the time got prepared 30min. Made to the flight barely but got stressed too much.

Seats too hard, too much lumbar. Space between rows was extremely tight, so tight hard to place item under seat in front of me. No tv screens. Zero plugs for charging phones. Too many sales pitches

It was a short fight and even though we had a delay due to weather we arrived on time

Worst airline ever! The guy weighing my bag had his foot on the metal plate and when I called him out on it, I got this stupid little smirk. La is a scam and so is Spirit Airlines. All the flight attendants looked like they hated our flight just as much as we did.

Very dissatisfied with spirit airlines after buying my ticket's they cancelled our flights with no reasoning.

Spirit is awful. Too expensive for what you get. Stop nickel and diming.

Good crew and safe. However, comfort and being nickeled-and-dimed are my issues. $75 each way for luggage is exhortation. The space to the next seat is so close you cannot open a laptop. The magazine rack doesn’t hold your items. Not a fan.

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