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$88+ Cheap flights from Midway (MDW) 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 3/10. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — CHS
Feb 20 — Feb 271
Fri 2/20
Fri 2/27
1 adult, Economy
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Cheap flight deals from Midway to Charleston

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

This Kiwi.com deal was found by Cheapflights users on 1/21. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/107:30 am
MDW
-
CHS
1 stop7h 35m
Multiple Airlines
Thu 3/126:15 am
CHS
-
MDW
2 stops14h 32m
Multiple Airlines
Deal found 1/21$278
This Southwest deal was found by Cheapflights users on 1/20. 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.
Tue 3/1012:45 pm
MDW
-
CHS
Nonstop2h 05m
Southwest
Tue 3/244:35 pm
CHS
-
MDW
Nonstop2h 20m
Southwest
Deal found 1/20$285
This Kiwi.com deal was found by Cheapflights users on 1/20. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/169:51 pm
MDW
-
CHS
1 stop9h 47m
Multiple Airlines
Thu 3/198:07 am
CHS
-
MDW
2 stops12h 40m
Multiple Airlines
Deal found 1/20$290
This Southwest deal was found by Cheapflights users on 1/20. 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 2/143:10 pm
MDW
-
CHS
Nonstop2h 00m
Southwest
Tue 2/178:15 am
CHS
-
MDW
Nonstop2h 15m
Southwest
Deal found 1/20$291
This Kiwi.com deal was found by Cheapflights users on 1/20. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/267:30 am
MDW
-
CHS
1 stop7h 30m
Multiple Airlines
Wed 4/18:07 am
CHS
-
MDW
2 stops15h 12m
Multiple Airlines
Deal found 1/20$292
This Southwest deal was found by Cheapflights users on 1/21. 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 4/113:30 pm
MDW
-
CHS
Nonstop2h 05m
Southwest
Wed 4/157:15 am
CHS
-
MDW
Nonstop2h 15m
Southwest
Deal found 1/21$295
This Kiwi.com deal was found by Cheapflights users on 1/21. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/196:05 am
MDW
-
CHS
2 stops15h 28m
Multiple Airlines
Mon 3/233:21 pm
CHS
-
MDW
1 stop25h 12m
Multiple Airlines
Deal found 1/21$296
This Kiwi.com deal was found by Cheapflights users on 1/21. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/239:22 pm
MDW
-
CHS
1 stop10h 16m
Multiple Airlines
Sat 2/286:35 pm
CHS
-
MDW
2 stops44h 54m
Multiple Airlines
Deal found 1/21$298
This Southwest deal was found by Cheapflights users on 1/21. 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 3/1012:45 pm
MDW
-
CHS
Nonstop2h 05m
Southwest
Thu 3/125:45 pm
CHS
-
MDW
Nonstop2h 20m
Southwest
Deal found 1/21$299
This Southwest deal was found by Cheapflights users on 1/20. 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.
Tue 3/1712:45 pm
MDW
-
CHS
Nonstop2h 05m
Southwest
Thu 3/195:45 pm
CHS
-
MDW
Nonstop2h 20m
Southwest
Deal found 1/20$302

Find flight deals from Midway to Charleston

Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) 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 January 21, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

Expedia
3 stars

Round-trip from

$278
(Kiwi.com)

One-way from

$88
(Trip.com)

Popular in

February

Cheapest in

October

Average price

$374

Good round-trip deal

$334 or less

Good one-way deal

$313 or less
Provider with most accurate pricing for Chicago Midway-Charleston flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago Midway-Charleston flights.
Search Deals
From Chicago Midway to Charleston
Search Deals
One-way flight from Chicago Midway to Charleston
Search Deals
Highest demand for flights based on searches. 8% potential increase in price ($30 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($10 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals
Price to beat on a round-trip flight from Chicago Midway to Charleston.
Search Deals
Price to beat on a one-way flight from Chicago Midway to Charleston.
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Midway 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 January 21, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Charleston that are best for you.

Fly from

Midway

Fly to

Charleston

Route

Depart

Return

Price

ChicagoCharleston

MDW - CHS

MDWCHS

Chicago Midway

Tue 4/14

9:50 am-5:40 pm

1 stop6h 50m

Charleston

Tue 4/21

7:15 am-8:30 am

Nonstop2h 15m

$295

ChicagoCharleston

MDW - CHS

MDWCHS

Chicago Midway

Tue 3/10

12:45 pm-3:50 pm

Nonstop2h 05m

Charleston

Thu 3/12

5:45 pm-7:05 pm

Nonstop2h 20m

$299

ChicagoCharleston

MDW - CHS

MDWCHS

Chicago Midway

Sat 4/11

3:30 pm-6:35 pm

Nonstop2h 05m

Charleston

Wed 4/15

7:40 am-2:20 pm

2 stops7h 40m

$300

ChicagoCharleston

MDW - CHS

MDWCHS

Chicago Midway

Wed 4/8

10:45 am-3:46 pm

1 stop4h 01m

Charleston

Sat 4/11

5:27 am-9:56 am

1 stop5h 29m

$305

ChicagoCharleston

MDW - CHS

MDWCHS

Chicago Midway

Sat 4/18

5:31 pm-11:50 pm

1 stop5h 19m

Charleston

Sat 4/25

7:05 am-12:30 pm

1 stop6h 25m

$305

ChicagoCharleston

MDW - CHS

MDWCHS

Chicago Midway

Wed 3/11

10:45 am-5:10 pm

1 stop5h 25m

Charleston

Sat 3/14

6:30 am-9:56 am

1 stop4h 26m

$305

ChicagoCharleston

MDW - CHS

MDWCHS

Chicago Midway

Wed 2/18

2:35 pm-7:10 pm

1 stop3h 35m

Charleston

Wed 2/25

9:05 am-4:45 pm

1 stop8h 40m

$305

ChicagoCharleston

MDW - CHS

MDWCHS

Chicago Midway

Sat 3/7

4:35 pm-9:40 pm

1 stop4h 05m

Charleston

Tue 3/10

4:35 pm-5:55 pm

Nonstop2h 20m

$309

ChicagoCharleston

MDW - CHS

MDWCHS

Chicago Midway

Sat 4/18

9:15 am-8:15 pm

1 stop10h 00m

Charleston

Sat 4/25

8:00 am-9:15 am

Nonstop2h 15m

$311

ChicagoCharleston

MDW - CHS

MDWCHS

Chicago Midway

Wed 3/11

3:35 pm-9:10 pm

1 stop4h 35m

Charleston

Sat 3/14

6:15 am-12:00 pm

1 stop6h 45m

$315

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/19

Showing 1-10 of 21 results
1
2
3

Compare providers for flights from Midway 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 Midway to Charleston in January.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star

*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 Midway Airport-Charleston flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago Midway Airport-Charleston flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago Midway Airport-Charleston flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago Midway Airport-Charleston flights, Cheapflights users trust Expedia the most. Expedia 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 Midway Airport-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 Midway to Charleston

Have a flexible travel schedule? Discover the best time to fly to Charleston from Midway 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 Midway Airport to Charleston

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

Currently, May is the cheapest month in which you can book a flight from Chicago Midway Airport to Charleston (average of $46). Flying from Chicago Midway Airport to Charleston in December is currently the most expensive (average of $362). 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 MDW to CHS?

Find hourly flight availability from Midway 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 January 21, 2026.

Unlike in the morning, when flights are generally more expensive, you can save up to 10% on flights from Chicago Midway Airport to Charleston by exploring options for tickets at noon.

The best insider tips for Chicago Midway Airport 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 Midway Airport to Charleston trip
Our travel experts
Ramsey Qubein

Ramsey Qubein

Expert on 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 January 21, 2026.
See what other customers who have flown with Southwest from Chicago Midway Airport to Charleston have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,266 reviews

Entertainment

7.5

Overall

8.0

Comfort

8.0

Crew

8.6

Food

7.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Southwest
8.0
Very good
4,266 reviews
Southwest
8.0
Very good
4,266 reviews

Entertainment

7.5

Overall

8.0

Comfort

8.0

Crew

8.6

Food

7.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

Related info for your journey

Find useful and relevant information for your journey from Midway 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 Midway?

    Charleston (CHS), located 10.2 mi from the city center, is the airport you fly into when you book flights from Chicago Midway to Charleston. 1 airline have flights to Charleston from Chicago Midway on a regular basis. Booking flights from Chicago Midway to Charleston should not be difficult; the airport handles an average of 0 inbound flights from Chicago Midway per day.

  • How long is the flight from Chicago Midway Airport to Charleston?

    A quick flight from Chicago Midway Airport to Charleston can take about 4h 01m. Southwest provides one of the quickest options available for as low as $305. Chicago Midway Airport and Charleston are separated by a distance of 745 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • What is the cheapest airline to fly from Chicago Midway Airport to Charleston round-trip?

    According to our current data, Southwest ($245), offers the cheapest pricing from Chicago Midway Airport to Charleston. Users have found that Southwest is 27% cheaper than the other options available to this destination.

  • What are the cheapest flights from Chicago Midway Airport to Charleston?

    Looking at all options, your cheapest flight can be booked for $301. While the most popular route (Chicago Midway - Charleston) can be booked for $244 on average, our data indicates $337 when flying from Chicago Midway Airport to Charleston.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Midway 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 Midway Airport to Charleston?

    Currently, May is the cheapest month in which you can book a flight from Chicago Midway Airport to Charleston (average of $46). Flying from Chicago Midway Airport to Charleston in December is currently the most expensive (average of $362). 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
Summerville
Walterboro
Isle of Palms
Mount Pleasant
Edisto Beach

Browse thousands of different options on Cheapflights for your next trip

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Top airline flying from Midway to Charleston

Discover the top airline that operate flights from Midway 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 January 21, 2026.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$245Average$317FlexibilityNo cancel feeOn-time63%

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