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$84+ Cheap flights from Chicago (CHI) to Charleston (CHS)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 5/10. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — CHS
May 21 — May 281
Thu 5/21
Thu 5/28
1 adult, Economy
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Find cheap flights from Chicago to Charleston with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

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3. Compare prices and book

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Cheapflights Tip: The best prices from Chicago to Charleston are usually found in August or January, booked 60 days in advance, depart on a Tuesday or Monday and return on a Friday

Cheap flight deals from Chicago to Charleston

Cheapest flights from Chicago to Charleston
Explore the most affordable flight options available from Chicago to Charleston. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 21, 2026.

This United Airlines deal was found by Cheapflights users on 4/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/199:00 am
ORD
-
CHS
Nonstop2h 17m
United Airlines
Tue 5/266:00 am
CHS
-
ORD
Nonstop2h 33m
United Airlines
Deal found 4/21$272
This Southwest deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/66:10 pm
MDW
-
CHS
Nonstop2h 05m
Southwest
Mon 6/84:45 pm
CHS
-
MDW
1 stop3h 50m
Southwest
Deal found 4/20$272
This Kiwi.com deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/48:30 am
ORD
-
CHS
1 stop12h 23m
Multiple Airlines
Fri 5/82:39 pm
CHS
-
ORD
2 stops33h 36m
Multiple Airlines
Deal found 4/19$273
This Southwest deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/106:20 pm
MDW
-
CHS
Nonstop2h 05m
Southwest
Tue 6/302:10 pm
CHS
-
MDW
1 stop3h 55m
Southwest
Deal found 4/20$273
This Southwest deal was found by Cheapflights users on 4/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/196:00 pm
MDW
-
CHS
Nonstop2h 05m
Southwest
Tue 5/267:15 am
CHS
-
MDW
Nonstop2h 15m
Southwest
Deal found 4/21$274
This American Airlines deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/287:41 pm
ORD
-
CHS
Nonstop2h 19m
American Airlines
Mon 6/17:50 pm
CHS
-
ORD
1 stop5h 15m
American Airlines
Deal found 4/16$275
This Southwest deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/93:30 pm
MDW
-
CHS
Nonstop2h 05m
Southwest
Mon 5/112:15 pm
CHS
-
MDW
1 stop4h 35m
Southwest
Deal found 4/16$275
This Kiwi.com deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/15:06 pm
ORD
-
CHS
1 stop19h 26m
Spirit Airlines
Fri 7/32:27 pm
CHS
-
ORD
1 stop26h 44m
Spirit Airlines
Deal found 4/17$276
This Southwest deal was found by Cheapflights users on 4/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/116:50 pm
MDW
-
CHS
Nonstop2h 05m
Southwest
Thu 5/147:40 am
CHS
-
MDW
Nonstop2h 15m
Southwest
Deal found 4/21$276
This Southwest deal was found by Cheapflights users on 4/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/227:20 am
MDW
-
CHS
2 stops7h 35m
Southwest
Mon 8/247:00 am
CHS
-
MDW
Nonstop2h 10m
Southwest
Deal found 4/21$277
This Kiwi.com deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/18:52 pm
ORD
-
CHS
1 stop12h 23m
Multiple Airlines
Sat 5/163:44 pm
CHS
-
ORD
1 stop7h 30m
Multiple Airlines
Deal found 4/19$278
This Southwest deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/2712:50 pm
MDW
-
CHS
2 stops6h 35m
Southwest
Sat 5/308:00 am
CHS
-
MDW
Nonstop2h 15m
Southwest
Deal found 4/20$278

Find flight deals from Chicago to Charleston

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Charleston (CHS). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated April 21, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$272
(Southwest)

One-way from

$84
(Delta)

Popular in

March

Cheapest in

August

Average price

$389

Good round-trip deal

$336 or less

Good one-way deal

$194 or less
Provider with most accurate pricing for Chicago (CHI)-Charleston flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Charleston flights.
Search Deals
From Chicago (CHI) to Charleston
Search Deals
One-way flight from Chicago (CHI) to Charleston
Search Deals
Highest demand for flights based on searches. 4% potential increase in price ($18 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($5 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 2026
Search Deals
Price to beat on a round-trip flight from Chicago (CHI) to Charleston.
Search Deals
Price to beat on a one-way flight from Chicago (CHI) to Charleston.
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to Charleston that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated April 21, 2026.
Use the filters below to find and compare flights from Chicago to Charleston that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoCharleston

MDW - CHS

MDWCHS

Chicago Midway

Sat 6/6

6:10 pm-9:15 pm

Nonstop2h 05m

Charleston

Mon 6/8

4:45 pm-7:35 pm

1 stop3h 50m

$272

ChicagoCharleston

MDW - CHS

MDWCHS

Chicago Midway

Mon 5/11

3:50 pm-8:50 pm

1 stop4h 00m

Charleston

Thu 5/14

7:40 am-8:55 am

Nonstop2h 15m

$275

ChicagoCharleston

ORD - CHS

ORDCHS

Chicago O'Hare Intl

Fri 6/19

5:40 pm-12:45 am

1 stop6h 05m

Charleston

Sun 6/21

7:59 pm-11:59 pm

1 stop5h 00m

$284

ChicagoCharleston

MDW - CHS

MDWCHS

Chicago Midway

Sat 5/23

10:45 am-5:16 pm

1 stop5h 31m

Charleston

Tue 5/26

5:15 am-10:00 am

1 stop5h 45m

$298

ChicagoCharleston

MDW - CHS

MDWCHS

Chicago Midway

Sat 6/20

4:25 pm-10:06 pm

1 stop4h 41m

Charleston

Wed 6/24

5:10 am-10:07 am

1 stop5h 57m

$299

ChicagoCharleston

ORD - CHS

ORDCHS

Chicago O'Hare Intl

Sat 8/8

5:18 pm-10:44 pm

1 stop4h 26m

Charleston

Sat 8/15

7:10 am-12:39 pm

1 stop6h 29m

$304

ChicagoCharleston

ORD - CHS

ORDCHS

Chicago O'Hare Intl

Sat 6/6

8:10 am-2:03 pm

1 stop4h 53m

Charleston

Sat 6/13

5:03 pm-8:59 pm

1 stop4h 56m

$304

ChicagoCharleston

MDW - CHS

MDWCHS

Chicago Midway

Sat 5/23

12:05 pm-9:00 pm

1 stop7h 55m

Charleston

Sat 5/30

7:00 am-1:10 pm

1 stop7h 10m

$310

ChicagoCharleston

MDW - CHS

MDWCHS

Chicago Midway

Fri 5/15

3:50 pm-8:50 pm

1 stop4h 00m

Charleston

Mon 5/18

7:55 pm-11:30 pm

1 stop4h 35m

$320

ChicagoCharleston

MDW - CHS

MDWCHS

Chicago Midway

Thu 6/4

12:45 pm-9:55 pm

2 stops8h 10m

Charleston

Tue 6/9

1:50 pm-9:35 pm

2 stops8h 45m

$321

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/16

Showing 1-10 of 42 resultsSorted by cheapest first
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Compare providers for flights from Chicago to Charleston

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Chicago to Charleston in April.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
PricelinePrice Accuracy1 starTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Chicago-Charleston flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-Charleston flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago-Charleston flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago-Charleston flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago-Charleston flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Chicago to Charleston

Have a flexible travel schedule? Discover the best time to fly to Charleston from Chicago with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Chicago to Charleston

How far ahead should I book a flight from Chicago to Charleston?

Use this chart to determine the optimal time to book a round-trip flight from Chicago to Charleston. Price data was last updated on April 17, 2026.

The price you pay for your flight from Chicago to Charleston may vary depending on when you book. For the best chance of a lower fare, look to book 60 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

What is the cheapest month to book a flight from Chicago to Charleston?

Currently, February is the cheapest month in which you can book a flight from Chicago to Charleston (average of $101). Flying from Chicago to Charleston in June is currently the most expensive (average of $227). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from CHI to CHS?

Find hourly flight availability from Chicago to Charleston. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated April 21, 2026.

When flying from Chicago to Charleston, the time of day you fly usually plays a role in the price. Save by searching for a flight at noon, which can drop the price by up to 7% versus a flight in the morning.

What is the cheapest day to fly from Chicago to Charleston?

Use this chart to determine the cheapest time to fly round-trip from Chicago to Charleston. Price data was last updated on April 18, 2026.

Travelers seeking maximum savings on their Chicago to Charleston flight should consider departing on Sunday at noon when fares are most often at their lowest. Sunday evenings flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from Chicago to Charleston

Explore weekly flight availability from Chicago to Charleston. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated April 21, 2026.

The most flights from CHI to CHS are scheduled on a Monday (20 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (16 on average).

How much does it cost to fly round-trip from Chicago to Charleston?

The best insider tips for Chicago to Charleston flights

AI-powered summary based on content written by travel experts. AI can make mistakes.
Cheapflights partnered with top experts to bring you the best recommendations for your Chicago to Charleston trip
Our travel experts
Ramsey Qubein

Ramsey Qubein

Expert on ORD, MDW and CHS

An avid traveler and aviation expert who has visited 173 countries, all 50 states and seven continents, Ramsey Qubein flies nearly 400,000 miles a year. As a North Carolina-based freelance journalist for publications including Conde Nast Traveler, Forbes, USA Today and Bloomberg among others, he explores the latest trends in aviation, hospitality, cruises and business.

Read more

Reviews of airlines servicing Charleston

Get insights into the airlines that provide service to Charleston. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Charleston. Reviews last updated April 21, 2026.
Read reviews from past customers who have flown Southwest,Delta, andUnited Airlines from Chicago to Charleston. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,331 reviews

Food

7.0

Entertainment

7.5

Comfort

8.0

Boarding

8.1

Crew

8.6

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Southwest
8.0
Very good
4,331 reviews
Southwest
8.0
Very good
4,331 reviews

Food

7.0

Entertainment

7.5

Comfort

8.0

Boarding

8.1

Crew

8.6

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Delta
7.9
Good
8,434 reviews
Southwest
8.0
Very good
4,331 reviews

Food

7.0

Entertainment

7.5

Comfort

8.0

Boarding

8.1

Crew

8.6

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
United Airlines
7.4
Good
9,613 reviews
Southwest
8.0
Very good
4,331 reviews

Food

7.0

Entertainment

7.5

Comfort

8.0

Boarding

8.1

Crew

8.6

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
American Airlines
7.1
Good
11,645 reviews
Southwest
8.0
Very good
4,331 reviews

Food

7.0

Entertainment

7.5

Comfort

8.0

Boarding

8.1

Crew

8.6

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

Related info for your journey

Find useful and relevant information for your journey from Chicago to Charleston. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to Charleston from Chicago?

    For a flight from Chicago to Charleston, you will be flying into Charleston. Charleston (CHS) is just 10.2 mi from the center of the city. Charleston is the only Charleston airport and it handles 18 inbound flights from Chicago per day. 5 airlines have flights to Charleston from Chicago on a regular basis.

  • How long is the flight from Chicago to Charleston?

    Departing from Chicago to Charleston will take you 2h 05m. The distance between Chicago and Charleston is about 745 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the cheapest airlines flying from Chicago to Charleston round-trip?

    Flying on Spirit Airlines is currently your cheapest option to Charleston, with prices starting at $109. Additional round-trip tickets that might be worth considering are offered by Delta and Southwest, with the lowest prices starting at $149 and $153, respectively. You may be able to fly from Chicago to Charleston for 71% less than the average price by searching for these airlines.

  • What are the cheapest airlines to fly from Chicago to Charleston one-way?

    To fly one-way, consider booking your trip with United Airlines, which is currently one of the cheapest options available, starting at $124. American Airlines flights start at $129 while deals on Southwest start at $169 one-way.

  • What are the most reliable airlines from Chicago to Charleston?

    No one likes to see their flight delayed. When booking a flight from Chicago to Charleston consider choosing Republic Airways (80%), Envoy Air (80%) or American Airlines (77%) as they are the most reliable in getting you off to your destination on time.

  • What are the cheapest flights from Chicago to Charleston?

    Looking at all options, your cheapest flight can be booked for $132. While the most popular route (Chicago O'Hare Intl - Charleston) can be booked for $225 on average, our data indicates $506 when flying from Chicago to Charleston.

  • Can I find deals for flights from Chicago to Charleston that include hotel bookings?

    Yes. In addition to deals on Chicago to Charleston flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Charleston?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Charleston.

  • Can I find deals for business class flights from Chicago to Charleston?

    Yes. Cheapflights offers flight deals from Chicago to Charleston by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago to Charleston?

    Currently, February is the cheapest month in which you can book a flight from Chicago to Charleston (average of $101). Flying from Chicago to Charleston in June is currently the most expensive (average of $227). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Charleston?

Book flights to Charleston if you plan to visit one of these locations
North Charleston
Santee
Walterboro
Summerville
Isle of Palms
Mount Pleasant
Goose Creek
Edisto Beach

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Alternative routes for Chicago to Charleston

See prices for flight routes from nearby airports that may be better suited for you.
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Top 5 airlines flying from Chicago to Charleston

Discover the top 5 airlines that operate flights from Chicago to Charleston. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated April 21, 2026.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$109Average$179FlexibilityNo cancel feeOn-time65%
DeltaCheapest$149Average$238FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$153Average$377FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$208Average$363FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$231Average$397FlexibilityNo cancel feeOn-time69%

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