$99 Find Cheap Flights from Chicago to Kiawah Island - Compare and Save

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 8/25. 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
$237
Typical prices: $284-$378
Southwest
Thu 10/29Mon 11/2
MDW - CHS • Non-stop
Cheapest non-stop
$237
Typical prices: $325-$469
American Airlines
Thu 10/22Sat 10/24
ORD - CHS • Non-stop
Arrival airport
You can't fly directly to Kiawah Island. It is served by Charleston (CHS), located 19.9 miles from Kiawah Island.
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Flight Deals
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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

Thu, Oct 29 - Mon, Nov 2
Southwest Logo
12:55 pm - 4:05 pm
MDW
-
CHS
2h 10mnonstop
Southwest Logo
7:10 pm - 8:25 pm
CHS
-
MDW
2h 15mnonstop
$237Southwest
Sat, Sep 12 - Sat, Sep 19
Southwest Logo
3:05 pm - 6:15 pm
MDW
-
CHS
2h 10mnonstop
Southwest Logo
7:35 am - 8:45 am
CHS
-
MDW
2h 10mnonstop
$237Southwest
Sat, Sep 12 - Sat, Sep 19
American Airlines Logo
9:52 am - 1:15 pm
ORD
-
CHS
2h 23mnonstop
American Airlines Logo
7:46 pm - 9:30 pm
CHS
-
ORD
2h 44mnonstop
$237American Airlines
Thu, Oct 22 - Sat, Nov 7
American Airlines Logo
8:40 pm - 11:59 pm
ORD
-
CHS
2h 19mnonstop
American Airlines Logo
4:15 pm - 5:59 pm
CHS
-
ORD
2h 44mnonstop
$237American Airlines
Sat, Sep 5 - Sun, Sep 6
United Airlines Logo
7:05 am - 10:36 am
ORD
-
CHS
2h 31mnonstop
United Airlines Logo
6:30 am - 8:00 am
CHS
-
ORD
2h 30mnonstop
$237United Airlines
Wed, Aug 26 - Tue, Sep 1
Multiple Airlines Logo
5:59 pm - 8:38 am
ORD
-
CHS
13h 39m
1 stop
Multiple Airlines Logo
3:13 pm - 11:08 pm
CHS
-
ORD
8h 55m
1 stop
$237Multiple Airlines
Thu, Aug 20 - Mon, Aug 24
Southwest Logo
7:35 am - 10:55 am
MDW
-
CHS
2h 20mnonstop
Southwest Logo
7:00 am - 8:10 am
CHS
-
MDW
2h 10mnonstop
$237Southwest
Thu, Oct 22 - Thu, Nov 5
American Airlines Logo
8:40 pm - 11:59 pm
ORD
-
CHS
2h 19mnonstop
American Airlines Logo
12:16 pm - 2:00 pm
CHS
-
ORD
2h 44mnonstop
$237American Airlines
Tue, Aug 25 - Tue, Sep 1
Multiple Airlines Logo
8:05 am - 6:14 pm
ORD
-
CHS
9h 09m
1 stop
Multiple Airlines Logo
3:13 pm - 11:08 pm
CHS
-
ORD
8h 55m
1 stop
$238Multiple Airlines
Sat, Oct 24 - Tue, Oct 27
United Airlines Logo
8:50 am - 3:00 pm
ORD
-
CHS
5h 10m
1 stop
United Airlines Logo
7:52 pm - 11:39 pm
CHS
-
ORD
4h 47m
1 stop
$240United Airlines
Useful Info

Good to know

Low season

February

Cheapest flight

$99
Best time to beat the crowds with an average 4% drop in price.
Most popular time to fly with an average 2% 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?

    28 direct flights run between Chicago and Kiawah Island on a daily basis. On average, there are about 201 departures each week.

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

    Consider leaving on a Tuesday and avoid Sundays 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 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 5 days, the cheapest one-way ticket between Chicago and Kiawah Island found on KAYAK was with American Airlines for $124. Southwest offered a round-trip connection from $245 and United Airlines from $250.

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 25 days before departure, on average.
  • Book at least 3 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.

Reviews of the top 3 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 4229 reviews
8.6Crew
8.0Comfort
7.0Food
7.5Entertainment
8.1Boarding
Airline reviews

Boarding process of asking for volunteers to check bags goes against the system you had before with 2 bags checked free. This process is more of a guilt trip than a caring attitude toward the customer. In addition bag-size scrutiny has increased which also slows down the process of boarding. My wife said she will not fly on your airline again unless there is no other option.

10.0 ExcellentDenis, Aug 2026
MDW - ATL
Read more Southwest reviews

Boarding process of asking for volunteers to check bags goes against the system you had before with 2 bags checked free. This process is more of a guilt trip than a caring attitude toward the customer. In addition bag-size scrutiny has increased which also slows down the process of boarding. My wife said she will not fly on your airline again unless there is no other option.

Overall good, just screaming kids in the area the whole flight.

OKay. I sat in the back of the plane and it was really loud between babies and little kids, and adults who.like to talk a lot and loudly most of the flight.

The first time I flew in the extra legroom section. It was difficult to notice a difference. I had bad luck with my neighbors. The crew was okay. Southwest has reduced the live TV options.

I flew twice this week on Southwest, was delayed over 2 hours both ways. From Pittsburgh to Chicago it was due to weather but the gate agents, pilot etc were great at updating everyone. Today from Midway to Pittsburgh the plane had come from an international location, kept getting delayed, no information was given until we were delayed for the third time. It was ridiculous, whoever scheduled that plane to fly to Pittsburgh after didn’t consider a lot of things.

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

Plane crashed into a bus or some other vehicle on the ground while pulling out of the gate. No injuries, but wing tip was damaged and returned to gate for “maintenance issues” and we departed 5 hours later because the plane went out of service and new plane was flown in from a nearby airport, Midway.

All was good. I just had a hard time getting connected to the WiFi/internet during the flight

after landing, we stay 2 hours on the taxi way before reaching the gate The airline and the crew were good though

I'm not a fan of Southwest's model. I don't like the herding style of boarding.

It was hot and not as comfortable as the flight to Chicago. Must have been a different plane that needs to be worked on or replaced.

The SFO lounge closes at 12 midnight. My flight took off at 2AM

It was extremely hot in the cabin the entire flight, vent air was worn

Have not had a flight out or returning to Norfolk that has not required maintenance, and a gate delay. Properly staff the crew so maintenance can be performed without last minute emergencies on each flight and there is enough staff to have gates prepared for inbound flights. Staff to ensure the safety and on time service vs. profit.

My original flight was cancelled and that affected my trip and my plans and I got no compensation and customer service was hard to reach as well

The flight was delayed by a hour and I wish they had communicated it sooner. No issues on the plane, it did take a while for food to come.

Know that the movies that you are going to be offered are the oldest be rated movies they could possibly get. They may have one or two new movies that they keep advertising but when you’re flying 15 hours, there is nothing to see past the first new movie.

Great experience. Boarding was fast, staff were very nice and funny, everything at the seat worked well.

Horrible! Several delays and then was cancelled! I spent over 24 hours in the airport and was unable to get a hotel or food voucher.

Awful. No counter attendants. No dinner offered due to delays.

I had my flight of Cedar Rapids. THen Chicago to Boston. Flight out of Cedar rapids was delayed by 12 hrs. Had to drive to Chicago to catch my flight

Long delays to board due to mechanical issues with plane.

Flight was delayed, boarded, sat at the gate for more than 30 minutes, left the gate then waited on the pad for another 30 to 60 minutes then returned to the gate, deboarded and was cancelled... alternative flight was not booked automatically. Waited in line for 30 minutes but fortunately an alternate flight to a different destination was found ... no thanks to the travel agent used by kayak

The flight from Milwaukee to Dallas was great the staff absolutely amazing. After that EVERYTHING WENT DOWN HILL!!! ABSOLUTELY HORRIBLE!!! WILL NOT FLY THIS AIRLINE AGAIN

I was very unhappy with the lack of communication from the cockpit. It took close to a half an hour before we took off after the doors were closed, and we got no announcements as to progress. It would be nice to get some acknowledgement of the situation and updates as to when we are taking off.

The seat was not even cleaned. It has full of cookie crums probably from last flight's passenger. Its basic expectation that, seats are clean.

Very turbulent flight, no drinks, very little service, unorganized boarding, gate changed multiple times

The flight was delayed significantly. Communication during the flight was abrupt and caused some panic as we were navigating turbulence. It was also too loud and every announcement felt startling. The flight attendants did not offer any assurances and I felt unsettled most of the flight. The seats, floor and tray table was very dirty. The seat next to me was broken and the passenger sitting there was very uncomfortable. He had a spring in his back and his seat made terrible squeaking noises through the flight.

Significant delays on my trip to Chicago and my trip back to NY

In-flight Wi-Fi didn’t work and the flight was 25 minutes late. The Embraer plane I was on was pretty old and the tray table was broken.

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

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