$58 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 2/21. 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

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Everything you should know

Cheapest round-trip
$259
Overall average: $436
Spirit Airlines
Sat 3/28Wed 4/1
ORD - CHS • 1 stop
Cheapest non-stop
$285
Typical prices: $366-$577
United Airlines
Tue 3/10Wed 3/11
ORD - CHS • Non-stop
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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

Sat, Mar 28 - Wed, Apr 1
Spirit Airlines Logo
6:16 pm - 4:00 pm
ORD
-
CHS
20h 44m
1 stop
Spirit Airlines Logo
5:02 pm - 12:07 am
CHS
-
ORD
8h 05m
1 stop
$259Spirit Airlines
Sat, Apr 25 - Mon, Apr 27
Multiple Airlines Logo
7:30 am - 2:40 pm
MDW
-
CHS
6h 10m
1 stop
Multiple Airlines Logo
7:00 am - 7:31 pm
CHS
-
MDW
13h 31m
2 stops
$259Multiple Airlines
Fri, Feb 13 - Sat, Feb 21
Spirit Airlines Logo
8:42 pm - 5:40 pm
ORD
-
CHS
19h 58m
2 stops
Spirit Airlines Logo
5:00 pm - 12:40 am
CHS
-
ORD
8h 40m
1 stop
$262Spirit Airlines
Mon, Mar 23 - Sun, Apr 5
Multiple Airlines Logo
6:10 pm - 10:13 pm
ORD
-
CHS
27h 03m
1 stop
Multiple Airlines Logo
8:07 am - 10:39 pm
CHS
-
ORD
39h 32m
2 stops
$263Multiple Airlines
Thu, Mar 19 - Mon, Mar 23
Multiple Airlines Logo
6:05 am - 10:33 pm
MDW
-
CHS
15h 28m
2 stops
Multiple Airlines Logo
5:02 pm - 1:02 pm
CHS
-
MDW
21h 00m
1 stop
$263Multiple Airlines
Sat, Feb 21 - Fri, Feb 27
Spirit Airlines Logo
7:00 am - 5:40 pm
ORD
-
CHS
9h 40m
1 stop
Spirit Airlines Logo
5:00 pm - 12:40 am
CHS
-
ORD
8h 40m
1 stop
$264Spirit Airlines
Mon, Feb 16 - Wed, Mar 4
Multiple Airlines Logo
9:22 pm - 8:38 am
MDW
-
CHS
10h 16m
1 stop
Multiple Airlines Logo
5:00 pm - 10:29 pm
CHS
-
MDW
30h 29m
2 stops
$264Multiple Airlines
Fri, Feb 13 - Mon, Feb 16
Spirit Airlines Logo
5:15 am - 5:40 pm
ORD
-
CHS
11h 25m
1 stop
Spirit Airlines Logo
6:35 pm - 11:47 pm
CHS
-
ORD
6h 12m
1 stop
$265Spirit Airlines
Fri, Feb 13 - Tue, Feb 17
Multiple Airlines Logo
4:42 pm - 5:40 pm
ORD
-
CHS
23h 58m
2 stops
Multiple Airlines Logo
3:01 pm - 3:52 pm
CHS
-
ORD
25h 51m
1 stop
$266Multiple Airlines
Mon, Feb 9 - Wed, Feb 11
Multiple Airlines Logo
5:15 am - 5:39 pm
ORD
-
CHS
11h 24m
1 stop
Multiple Airlines Logo
7:00 am - 8:13 am
CHS
-
ORD
26h 13m
1 stop
$267Multiple Airlines
Useful Info

Good to know

Low seasonJanuary
Cheapest flight$58
Best time to beat the crowds with an average 1% drop in price.
Most popular time to fly with an average 10% 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 00m.

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

    33 direct flights run between Chicago and Kiawah Island on a daily basis. On average, there are about 232 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 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 Saturdays.

  • 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 84 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 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 4267 reviews
7.5Entertainment
7.0Food
8.6Crew
8.1Boarding
8.0Comfort
Airline reviews

All good except once again bags took an hour at Midway Airport Happens all the time. Ridiculous

10.0 ExcellentAnonymous, Jan 2026
PHX - MDW
Read more Southwest reviews

All good except once again bags took an hour at Midway Airport Happens all the time. Ridiculous

Everything went smoothly and we even arrived a little bit early.

Great vacation. Can't wait till next year for another one.

Great flight but super high price. Glad it was a business trip and not personal

On time. Friendly staff. Took to long to pre bord all the specialty groups. Cramped small plane

The seats were comfortable, and the boarding process was pretty smooth.

3 hour delay. Had to change plans and was still delayed.

The staff was very friendly, professional, and courteous. The overall flight was a great experience.

The crew canceled the complementary snack and drink in anticipation of turbulence that never materialized. I was counting on the drink (water) to take the the doses of medication - prescribed for my heart condition - that were due during the flight. Since no snack or meal was served on this flight, I cannot rate the food quality. Otherwise, this flight was excellent.

Departure was delayed more than 1/2 hour while we waited for luggage (only) transfer from another flight/plane. Once approved for takeoff, the flight was excellent.

Delta One is extraordinary. I fly business when somebody hires me. I just wonder why there is such a chasm between business class and the insanely inhumane and nonsensical coach. The seats are not large enough to fit even my tiny wife. We fly 10% of what we did because we don’t want to pay 5-10 k but for $400 it’s unbearable. It seems like the accountants took over and made stupid decisions. Screw in 20 extra seats and make it so unbearable that people fly 90% less. Just put the damn price up and put some proper chairs in. But business, yay.

Timing, quality of service, promptness and courtesy of the staff

It was last minute due to weather - considering - it was amazing! Good smiles, friendly staff and they were making sure we knew what was going on when and where.

delta last minute gave me a boarding pass for a different flight with no confirmation that they were changing it

The service from the flight attendants were of supreme quality. They greeted and treated everyone with a wide smile. This is totally absent nowadays. Kudos to them!!!!

Excellent flight and got us around tough weather. Only issue was seat TV did not work and crew tried to reboot.

Very large passenger too space from my own seat. Arm board couldn’t be lowered because of his size. It wads very uncomfortable trip, as the flight was full couldn’t move anywhere having back pain because of the position in which I was the entire flight.

was sitting in the jet bridge for 10 minutes in -20 degree weather waiting for my bag

Outdated equipment in disrepair, wifi inoperable. Broken seats, taped air vents, generally poor condition, the 717 showed its age and lack of upkeep.

My flight out of Baton Rouge to Atlanta was delayed by a half hour. This got us into Atlanta airport 30 minutes late. I ran through the airport to get to my connecting flight. As I approached the boarding gate, I saw the boarding door was still open and a passenger was being checked in. But when I got to the gate, the boarding agent told me they had already given away my seat and there were no empty seats on that flight. So I had to take a later flight. That has never happened to me before. Very frustrating.

I was fully checked in the prior night and i was unchecked and then didn’t have a seat when I boarded. Instead of an aisle seat, I was out in the middle seat of the very last row of the plane.

In overall it was a good experience, the only down point was that the entertainment screen was working properly.

They lost my luggage, so, not happy. The crew was nice but my suitcases never made it, still trying to find out what happened!

I understand weather is an issue, but making us chase our plane down at five scheduled gates across three terminals in an airport the size of O'Hare was unfair. They'd have probably been better off to leave gates as TBD until the inbound plane is in final approach instead of running us all over the place. Also, props to the consistently-unprepared ground crew in Richmond for once again leaving my lane parked short of the gate because they couldn't have a crew in place on time with 2 hours notice...

cabin crew was OK, food was OK, the trip from the US to Munich was actually pretty bad comfort wise. Noisy aircraft, lights never dimmed even in Business class (night flight) barely sufficient amenities for the price. I have millions of miles with United but TBH American is gaining ground and Delta has always been marginally better then United although on paper United has more longes and cheaper upgrades.

Essy to get on. The hostess gave very little pop, the plane was late getting in, and we are still waiting for our bags. This sucks. :/

Great flight. On time boarding. Smooth flight and on time arrival at EWR. The flight crew was marvelous and there was a great selection of movies on the entertainment system. Our bags were at the carousel before we got there. Another excellent flight from United.

I liked the snacks and the flight attendants were friendly.

After a delay at the gate, C3, at Ohare on Sunday, I left my Blk ski coat on the bench at the gate, lost! Please review my lob claim, thx.

Very thoughtful flight attendant offered me water immediately since I had run to make my connection.

The aircraft had several problems - from excess fuel to non operational ac. Two hours of delay in Chicago could have been avoided with proper planning and aircraft maintenance.

Crew in Columbia was not prepared for landing. It was a bit of a disaster and getting bags took forever.

We were upgraded to First Class and it was a great flight

We experienced gate changes and a long delay. My seat was dirty when I boarded and I had to use wipes to clean it myself. There was an unpleasant and overpowering cleaning product scent on the plane as well that lingered through the flight.

My carry on baggage was damaged. Entire trip, I had to carry the baggage. When complained to the boarding crew, they got mad at me and still asked me to valet check in the cabin baggage. Rude boarding crew!!!

Crew were all friendly and helpful. It was a short flight so just a beverage service with a cookie. After we were boarded the plane took about 45 minutes to leave the gate but it was New Year’s Eve so not shocking there was some delay. Overall good experience and very grateful.

The boarding process needs to be fixed. The zone don't work, especially when there is hardly anyone in zones 3, 4,and 5, leaving the majority of the passengers backed up in the aisle, especially because passengers seated near the front are blocking passengers who are seated in the rear of the plane. It would also help if the size of carry on bags was more strictly enforced.

The boarding by groups is pointless. The first two groups worked fine, but almost Noone boarded in goups three thru five leaving the vast majority boarding when group six was called. It defeated the purpose of spreading out the crowd.

We loved the steward on the plane. He made the night enjoyable

The plane was late, when we did board the plane was as cold as a freezer. I was freezing the entire flight, no blankets. Lost miserable flight I’ve ever had.

it was terrible. flight was cancelled hours before the flight without a given reason and no other booking available .

Spirit Airlines has a reputation for being a terrible, cheap airline, this is why. I took a gamble on them, having never flown with them before, and the flight got cancelled. First they delayed the flight about 4 times before finally canceling it because a flight attendant didn’t show up to work that day. That’s so stupid. When I asked a ticketing agent she said that’s “company policy”. A company policy that inconveniences hundreds of passengers because a single flight attendant didn’t show is ridiculous and inefficient. I will never, ever try flying Spirit Airlines again.

Cancelled my flight and the earliest that they are willing give me for the next flight which was 3 days later on a weekday. Only accommodation they are willing to give was $30 airline credit that will expire in 1 year

Flight was canceled, huge lines to get baggage returned. Most other airlines had delays but not widespread cancellations like Spirit.

never ever fly spirit airlines you will be screwed in the end

I didn't eat, so I can't rate the food. Delayed set off was beyond

No Tumberlence smooth flight. Try to change the menu on Snacks.

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.

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

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