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Find cheap flights from Chicago to Kiawah Island from $50

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 5/30. 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
Sat 6/15
Sat 6/22

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Good to know

Low season

January

High season

June

Cheapest flight

$50
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 10m.

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

    20 direct flights run between Chicago and Kiawah Island on a daily basis. On average, there are about 142 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 Thursdays.

  • 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 $50. Frontier offered a round-trip connection from $194 and Spirit Airlines from $229.

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 10673 reviews
8.0Entertainment
7.4Food
8.2Boarding
7.9Comfort
8.6Crew
Airline reviews

5-hour delay due to storms in Tanoa and airspace restricted by Miami traffic controllers.

6.0 GoodGary, May 2024MSP - TPA
Read more about Delta reviews

5-hour delay due to storms in Tanoa and airspace restricted by Miami traffic controllers.

A regional sized plane was used for a cross country flight with no overhead bin space. I had to "pink check" my laptop and my medications. I was NOT pleased!!!!

Absolutely nothing flight was cancelled and delayed for 2 days. Barely a heads up I want a full refund

The plane from SNA wouldn’t start after 5 tries. The team gave me an option of flying direct from LAX and giving me a Lyft ride there! Perfect!

Best airline! Always friendly and welcoming. Skyclub was great and loved the fast free wifi on board. I also love that you can pre-order your meal on the app!

Atlanta boarding crew at gate were filled with arrogance and were disrespectful. In flight crew showed indifference to the needs of passengers. This is about the flight from ATL to BDL.

Boarding was somewhat chaotic. Unable to evaluate crew or food/drink because captain kept them seated due to turbulence. Have no idea if entertainment was offered.

The gate area was incredibly short staffed, with one representative manning 4-5 flights, which caused a 3 hr delay in boarding even though the plane was all ready to leave. Other flights also were delayed because of this. The flight crew was awesome and I feel bad for the only gate worker on call, but Delta needs to hire more employees.

Very frustrated with boarding gate crew. She announced the plane was small and they would be limiting us to one item to carry on. Not a problem for me as I understand the tiny planes have limited space!! Not the case here! It was a rather large plane and had plenty of room for bags! So because I don’t want to be one of “those people” who ignores the request to check a carry on I did so asking if I would be able to pick it up at the bottom of the ramp on arrival in Knoxville to which she responded “yes”! Then I watched as every other passenger held onto their 2 items and boarded!! Then when we arrived in Knoxville our 2 carry ons had been put with all the other luggage and we had to go to baggage pick up and wait for all the big checked bags to come off the carousel! So she lied!! Frustrating. Next time I won’t be so nice!

It was a good experience except when boarding a female flight attendant did not go out of her way to assist my teenage daughters in finding space for their carry-ons after their compartments were full.

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.

The control panel for the seat back screen did not work at all after takeoff.

Plane was so old it had cigarette butt trays in the seat

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

Deicing in Denver took forever and I almost missed my connection. De-ice faster! Not Americans fault.

Never been on this flight as i had missed it due to delayed connecting flight

Horrible. Delays, no customer support and fake promises and everything. i am suffering to help as due to connecting flight getting missed no support on ground and customer support window is closed and we are sitting o ground without anything

Missed our departing flight due to poor baggage drop staff. At the airport with 2 & 1/2 hours to spare and waited in bag check in until 15 minutes prior to gates closing before baggage staff asked us to move to the front of the line. We weren’t the only passengers that missed the flight. Poor organizational operations by Spirit staff. Otherwise , the return trip was fine.

My experience with Spirit was perfect. Did not expect it to be this good

Worst airline experience ever. Lost my IPad going thru security. Charged for my dog carriage at the gate not at ticket counter. Gave away my seat 6D. Expressed I wanted my seat back after charging me 99 for dog carriage. Should have thrown it out. Had a 16 yr old Yorkie heading to Boston after being a snowbird. Seats small. Very bad experience. Still don’t have my IPad. Horrible

My mother was HARASSED AND ACCOSTED by the gate agent for her bag. I pre purchased the bag fee and the gate agent made my 78 year old mother board, deplane, re pay for her bag fee and board again. The gate agent made my mother pick up her own bag and REFUSED to help her, she is an older woman who wasn’t bothering anyone on a flight that had maybe 30’total passengers. I am going to sue this airlines for their HORRIBLE customer service and treatment of my mother, and all this occurred the day after Mother’s Day!!!

The boarding gate was moved so many times that I missed my flight. No attendants would help me. The wrong gate was even on my boarding pass. I had to repurchase everything. I’ll never fly again. Really a terrible day as I had planned to see a former student who is dying in Louisville Never ever will I forget that day. Your airline is totally uncaring.

Seats are very small and extremely hard. Too close together. The person next to me had average shoulders and was very far into my 'space'.

The flight attendants were very personable, extremely friendly, and had a very good feeling of the energy around them not to mention they’re very funny and engaging. What made up for the discomfort of the seats and the fact that the plane sat for a long time on the Turmac. Not sure if the pilot was new, but the landing was very rough sort of like I was at a magic mountain theme park ride that was built in 1959

The price is good but I feel that carry-on bag could be a little low and snacks prices

Book cheap flights from Chicago to Kiawah Island

Recent round-trip flight deals

6/22Sat
1 stopFrontier
5h 08mMDW-CHS
6/24Mon
1 stopFrontier
6h 13mCHS-MDW
$194
6/25Tue
1 stopFrontier
11h 32mMDW-CHS
6/28Fri
1 stopFrontier
6h 14mCHS-MDW
$204
6/2Sun
3 stopsSpirit Airlines
25h 30mORD-CHS
6/8Sat
2 stopsSpirit Airlines
10h 18mCHS-ORD
$229
7/19Fri
1 stopSpirit Airlines
6h 28mORD-CHS
7/21Sun
1 stopSpirit Airlines
8h 35mCHS-ORD
$230
9/10Tue
1 stopDelta
6h 53mMDW-CHS
9/14Sat
1 stopDelta
3h 46mCHS-MDW
$236
6/3Mon
1 stopAmerican Airlines
6h 38mORD-CHS
6/12Wed
nonstopAmerican Airlines
2h 29mCHS-ORD
$239
6/18Tue
nonstopAmerican Airlines
2h 16mORD-CHS
6/25Tue
1 stopAmerican Airlines
4h 46mCHS-ORD
$241
7/31Wed
1 stopDelta
3h 58mMDW-CHS
8/6Tue
1 stopDelta
4h 17mCHS-MDW
$242
5/30Thu
nonstopUnited Airlines
2h 24mORD-CHS
6/4Tue
nonstopUnited Airlines
2h 27mCHS-ORD
$295
6/25Tue
nonstopUnited Airlines
2h 23mORD-CHS
7/1Mon
1 stopUnited Airlines
4h 33mCHS-ORD
$303

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Recent one-way flight deals

5/30Thu
1 stopSpirit Airlines
11h 57mORD-CHS
$50
6/12Wed
2 stopsSpirit Airlines
11h 41mORD-CHS
$55
6/19Wed
1 stopFrontier
4h 47mORD-CHS
$75
8/7Wed
1 stopFrontier
5h 11mORD-CHS
$85
7/5Fri
nonstopUnited Airlines
2h 22mORD-CHS
$109
6/11Tue
nonstopUnited Airlines
2h 23mORD-CHS
$115
6/19Wed
1 stopDelta
6h 32mMDW-CHS
$124
6/30Sun
1 stopAmerican Airlines
6h 42mORD-CHS
$148
6/30Sun
1 stopDelta
6h 32mMDW-CHS
$148
5/22Wed
nonstopAmerican Airlines
2h 23mORD-CHS
$169

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Last minute flights from Chicago to Kiawah Island

Last minute flight, train and bus deals

5/21Tue
multi-stopSpirit Airlines
11h 57mORD-CHS
5/22Wed
multi-stopSpirit Airlines
11h 37mCHS-ORD
$236
5/21Tue
multi-stopSpirit Airlines
28h 15mORD-CHS
5/28Tue
multi-stopSpirit Airlines
28h 43mCHS-ORD
$269
5/20Mon
multi-stop
19h 19mORD-CHS
5/29Wed
multi-stop
32h 11mCHS-ORD
$329
5/18Sat
multi-stop
28h 16mORD-CHS
5/29Wed
multi-stop
32h 11mCHS-ORD
$354
5/21Tue
multi-stopDelta
6h 47mMDW-CHS
5/22Wed
multi-stopDelta
5h 09mCHS-MDW
$456
5/20Mon
nonstopAmerican Airlines
2h 23mORD-CHS
5/29Wed
nonstopAmerican Airlines
2h 28mCHS-ORD
$476
5/18Sat
multi-stopAmerican Airlines
6h 44mORD-CHS
5/29Wed
nonstopAmerican Airlines
2h 28mCHS-ORD
$484
5/21Tue
nonstopUnited Airlines
2h 18mORD-CHS
5/22Wed
nonstopUnited Airlines
2h 31mCHS-ORD
$528
5/21Tue
nonstopUnited Airlines
2h 19mORD-CHS
5/22Wed
nonstopUnited Airlines
2h 39mCHS-ORD
$537
5/21Tue
multi-stopDelta
4h 22mMDW-CHS
5/22Wed
multi-stopDelta
5h 09mCHS-MDW
$547

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Flights to Kiawah Island