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Find cheap flights from Chicago to Kiawah Island from $51

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 7/2. 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
0 bags
Thu 7/4
Thu 7/11

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Good to know

Low season

January

High season

June

Cheapest flight

$51
Best time to beat the crowds with an average 13% drop in price.
Most popular time to fly with an average 7% 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 13m.

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

    21 direct flights run between Chicago and Kiawah Island on a daily basis. On average, there are about 150 departures each week.

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

    Consider leaving on a Saturday and avoid Fridays if you are looking for the best rates. For your return to Chicago, you’ll find the best rates on Tuesdays and the most expensive ones on Fridays.

  • 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 $51. Spirit Airlines offered a round-trip connection from $108 and American Airlines from $217.

See more FAQs

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 66 days before departure, on average.
  • Book at least 2 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 January.
See more tips

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
DeltaOverall score based on 10392 reviews
8.6Crew
7.4Food
8.0Entertainment
7.9Comfort
8.2Boarding
Airline reviews

It was good until there was a 3 hour delay because there was not any pilots to fly the plane.

2.0 MediocreFelipe, Jun 2024DTW - SAN
Read more about Delta reviews

It was good until there was a 3 hour delay because there was not any pilots to fly the plane.

There was plenty of overhead room but half of the passengers were told they had to check their carryon bags. My partner and I checked in as early as possible and our seats were split across the aisle.

Friendly flight attendants. Comfort plus seats were very comfortable and had lots of leg room. 10A and 10 B.

Flew first class so everything was great. But maybe because the flights were red eye, no meals were served, just chips. I flew Alaska Air 1st class at 9PM (2 hour flight) and they served beef short rib sliders!

Had to change aircraft due to a faulty door. Surprisingly it only caused about an hour and a half of delay. Delta handled this situation as well as can be expected.

Awful. Flight was continuously getting delayed and gates kept changing without any reason. Flight was delayed for more then 3 hours

Paid premium for Delta only to be on safe but tired old 767 with ancient cabin in mediocre condition. Poor wifi and horrible inflight entertainment. Hardly a premium experience. Should have flown SW and had fun flight crew and no pretense

Our flight to Zurich was delayed by almost 3 hours, so we missed our next flight. There was no indication it would be delayed this much. We were told the gate had changed and then it apparently took over 2 hours to load the "catering" on the plane. We were not compensated in any way for the trouble.

Rated entertainment as Mediocre as there were major problems with the Infotainment system that took probably a half hour for them to fix.

Your crew could maybe answer the call bell at least one of the times I pressed it. I pressed it first time with 2.5 hours left in our flight bc my partner was hungry and wanted a sandwich. We finally got the sandwich with 40 mins left in the flight.

Flighty delayed on boarding - then group 1 had to check their carry on bags but groups 3 and beyond could carry bags on - very inconvenient for weekend business trip with no checked baggage. Then delayed on the runway - before take off. No communication from pilot on why or how long. Wifi/Entertainment didn't work for 4+ flight. Upon arrival, attendants announced wrong carousel for baggage claim - everyone was waiting at the wrong place for their checked bags. This was a mess united!

There was no screens on board AND the WiFi didn’t work. My seat was broken and couldn’t recline so I couldn’t even sleep. The flight attendants didn’t offer anything to make it more comfortable. It was such an old cramped plane, when the person in front of me reclined I couldn’t even open my tray table. All the United ads talk about guaranteeing everyone gets a screen!

I’ve had a couple flights this week on United that were delayed by an hour or more

Great! The plane was decently sized and comfortable. The staff was nice and there was great in flight entertainment

Last minute gate change nearly caused us to miss our flight. Change was not announced or displayed in the main board at the old gate. Terrible communication. When we landed we had to wait 20 minutes because there was another plane at the assigned gate. Not the crew’s fault, but adding 20 minutes to a 45 minute flight sucked.

delay several times and wait extra long to board. no entertainment service because there are problem for some rows. always encounter some delays for the last flight of the day.

The flight experience was very good! Especially the United Club!

I was not able to buy food in the flight. They refer to include your Credit card in the APP, and if you are not from USA (i have a credit card form Canada) it is not possible

The flight from Ottawa to Chicago took a lot longer due to DC in Ottawa. We got to Chicago and went to our gate to catch our flight. We only had nine minutes I found that very stressful.

Good boarding. Crew started quick with drinks and food. They came around several times for trash which I really liked. Other than turbulence due to storms in the area, flight was great.

My husband and I pre-ordered our food, but they did not have my husband’s order, and my cheese plate was very average. I asked for a blanket and was told they don’t carry blankets on domestic routs. The flight was on time and smooth!

Good flights. Departure and arrivals were on time. DFW was a little problematic in that the Skytrain without prior notice bypassed the Echo terminal so that delayed my arrival at my connecting flight.

Because I can’t stand very long in one place, I was allowed to reword.

5 hour flight - full flight - not enough room to use my computer - slightly delayed - Admirals club was excellent quality food, drink made up for flight seating. No food offerred on flight, you ahd to prebook.

Excellent- plan was barely populated. I cannot remember a flight where I was able/encouraged to stretch out!

Great flight. Boarding was efficient and quick. On time departure and smooth flight. Flight arrived early at destination. Good experience.

Had technical issue which delayed the flight period. Flight crew knew there was 5 passengers that the connecting flight was within 15 minutes once at the gate. Rather than identify the 5 passengers to assure they got first. The flight attended mentioned it but didn't assist to assure passengers with connecting flights off first. This caused a hardship and our party of 3 missed the connecting flight.

I don't like that I have to pay if I want extra leg room. The seats are so expensive; I sit in normal seats and my legs and knees cramp the entire flight. I never feel comfortable on AA flights.

Flight was delayed at departure due to weather and the need for de-icing. The flight was smooth but there was a delay at arrival due to weather. We were in a hold for 20 minutes or more. The flight arrived more than 30 minutes late. Airlines have no control over the weather and I'm glad that they follow all safety procedures. Had to wait a long time for my checked luggage. Whole process was slow and the bags arrived wet due to the rain. The onboard wifi and entertainment access was spotty and the signal was dropped several times. Otherwise the crew was great and friendly. They tried to get everyone's bags stowed and seated so we could take off.

Regarding the boarding: it needs more efforts to make it more convenient

Flight was good and clean but delayed over an hour on the return flight.

The non stop flight and able to go into Atlantic City airport. They could lower the prices. It starts out low but then if you want to bring luggage and pick your seat the price goes up quite a bit.

Flight got diwngraded last minute and left us stranded. I was told I’ll be given credit for my luggage and seat upgrades but haven’t got anything yet

We can’t predict circumstances like this ahead of time, but I give your staff a hats off for immediately giving us updated informations.

It was nice! There was a very unhappy child in front of us and the flight attendant did a great job calming the child. I was impressed.

The plane was not on time for boarding or departure or arrivals.

EVERYTHING WAS WONDERFUL HOSPITALITY THE HELP.THE SEATING FRIENDLY ALWAYS HAVE A GOOD RIDE NOT ONE BAD EXPERIENCE WITH THEM

Flight expected to leave at 6:40 pm ended leaving at 8:00 am the following day. I slept in a cold airport. Never again Spirit for me…

This was the return leg of my journey with Spirit Airlines. Despite its reputation, I found no issues as it got me from point A to B safely and without delay, especially with no mechanical delays, which is fantastic in my book! The staff, from ground crew to cabin crew, were all pleasant and hassle-free. The flight was smooth from takeoff to landing. I have absolutely no complaints about this no-frills airline!

It was the worst ever, i will be filing a lawsuit to get a refund. Our flight was delayed 4 hours so we would miss our connecting flight, we were not rebooked to our destination the same day, we were not offered any options to get home on the same day despite being clear that we absolutely cannot get stranded at night due to family, we were forced to book our own flights on a different airline to get home, and spririt is refusing a refund because our flight wasn't cancelled, only delayed. oh yeah, and they lost our luggage on the first part of the trip and you cannot get a hold of customer service when anything goes wrong, on hold for 30+ minutes. and their app breaks so you can't use that either.

Book cheap flights from Chicago to Kiawah Island

Recent round-trip flight deals

9/21Sat
1 stopSpirit Airlines
5h 20mORD-CHS
9/26Thu
1 stopSpirit Airlines
5h 35mCHS-ORD
$108
7/16Tue
1 stopSpirit Airlines
7h 20mORD-CHS
7/17Wed
1 stopSpirit Airlines
5h 54mCHS-ORD
$110
6/26Wed
1 stopSpirit Airlines
6h 10mORD-CHS
6/29Sat
1 stopSpirit Airlines
5h 45mCHS-ORD
$113
9/11Wed
1 stop
5h 11mORD-CHS
9/12Thu
1 stop
5h 35mCHS-ORD
$114
9/11Wed
1 stop
5h 11mORD-CHS
9/16Mon
1 stop
5h 35mCHS-ORD
$127
8/17Sat
nonstopAmerican Airlines
2h 15mORD-CHS
8/24Sat
nonstopAmerican Airlines
2h 27mCHS-ORD
$217
8/17Sat
1 stopDelta
4h 31mORD-CHS
8/21Wed
1 stopDelta
6h 52mCHS-ORD
$236
8/17Sat
1 stopDelta
4h 47mMDW-CHS
8/24Sat
1 stopDelta
6h 34mCHS-MDW
$236
8/31Sat
nonstopAmerican Airlines
2h 15mORD-CHS
9/4Wed
1 stopAmerican Airlines
4h 04mCHS-ORD
$247
8/2Fri
nonstopUnited Airlines
2h 23mORD-CHS
8/5Mon
1 stopUnited Airlines
4h 33mCHS-ORD
$267

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Recent one-way flight deals

7/2Tue
1 stopSpirit Airlines
8h 53mORD-CHS
$51
9/12Thu
1 stopSpirit Airlines
12h 22mORD-CHS
$64
7/24Wed
1 stopFrontier
11h 28mORD-CHS
$91
7/23Tue
nonstopUnited Airlines
2h 23mORD-CHS
$115
8/2Fri
1 stopFrontier
11h 28mORD-CHS
$120
7/23Tue
1 stopDelta
5h 54mMDW-CHS
$124
10/4Fri
nonstopUnited Airlines
2h 20mORD-CHS
$129
7/27Sat
1 stopAmerican Airlines
4h 10mORD-CHS
$148
7/20Sat
1 stopDelta
4h 49mMDW-CHS
$148
7/14Sun
nonstopAmerican Airlines
2h 25mORD-CHS
$165

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Last minute flights from Chicago to Kiawah Island

Last minute flight, train and bus deals

6/8Sat
multi-stopFrontier
5h 08mMDW-CHS
6/10Mon
multi-stopFrontier
6h 13mCHS-MDW
$192
6/8Sat
multi-stopFrontier
5h 08mMDW-CHS
6/10Mon
multi-stopFrontier
6h 13mCHS-MDW
$195
6/8Sat
multi-stopFrontier
5h 08mMDW-CHS
6/17Mon
multi-stopFrontier
6h 13mCHS-MDW
$233
6/8Sat
multi-stop
7h 20mORD-CHS
6/19Wed
multi-stop
5h 45mCHS-ORD
$242
6/5Wed
multi-stop
4h 47mORD-CHS
6/12Wed
multi-stop
19h 04mCHS-ORD
$243
6/8Sat
multi-stop
7h 20mORD-CHS
6/12Wed
multi-stop
5h 45mCHS-ORD
$247
6/8Sat
multi-stopSpirit Airlines
28h 02mORD-CHS
6/11Tue
multi-stopSpirit Airlines
22h 06mCHS-ORD
$272
6/8Sat
multi-stopSpirit Airlines
28h 02mORD-CHS
6/10Mon
multi-stopSpirit Airlines
19h 04mCHS-ORD
$301
6/5Wed
multi-stopDelta
5h 12mMDW-CHS
6/12Wed
multi-stopDelta
4h 30mCHS-MDW
$574
6/6Thu
multi-stopDelta
4h 02mMDW-CHS
6/9Sun
multi-stopDelta
4h 30mCHS-MDW
$668

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Flights to Kiawah Island