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$109+ 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 9/1. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — CHS
Jul 4 — Jul 111
Sat 7/4
Sat 7/11
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 June 4, 2026.

This Southwest deal was found by Cheapflights users on 6/3. 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 7/156:20 pm
MDW
-
CHS
Nonstop2h 10m
Southwest
Tue 7/216:35 am
CHS
-
MDW
2 stops8h 00m
Southwest
Deal found 6/3$272
This Delta deal was found by Cheapflights users on 6/4. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/1511:05 am
MDW
-
CHS
1 stop5h 11m
Delta
Tue 7/217:06 am
CHS
-
MDW
1 stop6h 32m
Delta
Deal found 6/4$277
This Southwest deal was found by Cheapflights users on 5/31. 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 8/83:05 pm
MDW
-
CHS
Nonstop2h 05m
Southwest
Tue 8/117:35 am
CHS
-
MDW
Nonstop2h 10m
Southwest
Deal found 5/31$278
This Southwest deal was found by Cheapflights users on 6/1. 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 9/53:05 pm
MDW
-
CHS
Nonstop2h 05m
Southwest
Tue 9/87:20 pm
CHS
-
MDW
1 stop4h 00m
Southwest
Deal found 6/1$288
This Southwest deal was found by Cheapflights users on 6/1. 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 7/16:20 pm
MDW
-
CHS
Nonstop2h 05m
Southwest
Sat 7/45:30 am
CHS
-
MDW
Nonstop2h 10m
Southwest
Deal found 6/1$289
This Delta deal was found by Cheapflights users on 6/2. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/54:39 pm
MDW
-
CHS
1 stop4h 22m
Delta
Tue 9/84:30 pm
CHS
-
MDW
1 stop6h 16m
Delta
Deal found 6/2$298

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 June 4, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$272
(Southwest)

One-way from

$109
(Kiwi.com)

Popular in

March

Cheapest in

October

Average price

$389

Good round-trip deal

$377 or less

Good one-way deal

$172 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. 24% potential increase in price ($123 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 6% potential price decrease ($24 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in June 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 June 4, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Charleston that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoCharleston

MDW - CHS

MDWCHS

Chicago Midway

Wed 7/29

11:25 am-6:15 pm

1 stop5h 50m

Charleston

Tue 8/4

6:45 am-3:25 pm

2 stops9h 40m

$282

ChicagoCharleston

MDW - CHS

MDWCHS

Chicago Midway

Wed 7/15

10:00 am-6:15 pm

1 stop7h 15m

Charleston

Tue 7/21

2:10 pm-7:55 pm

2 stops6h 45m

$282

ChicagoCharleston

MDW - CHS

MDWCHS

Chicago Midway

Wed 7/8

6:20 pm-9:30 pm

Nonstop2h 10m

Charleston

Sat 7/11

5:30 am-6:40 am

Nonstop2h 10m

$289
Quickest round-trip

ChicagoCharleston

MDW - CHS

MDWCHS

Chicago Midway

Wed 6/24

6:20 pm-9:25 pm

Nonstop2h 05m

Charleston

Sat 6/27

5:30 am-6:40 am

Nonstop2h 10m

$307

ChicagoCharleston

MDW - CHS

MDWCHS

Chicago Midway

Fri 7/24

7:45 pm-10:55 pm

Nonstop2h 10m

Charleston

Tue 7/28

4:15 pm-10:00 pm

1 stop6h 45m

$333

ChicagoCharleston

MDW - CHS

MDWCHS

Chicago Midway

Fri 7/10

7:45 pm-10:55 pm

Nonstop2h 10m

Charleston

Tue 7/14

3:00 pm-7:35 pm

1 stop5h 35m

$333

ChicagoCharleston

MDW - CHS

MDWCHS

Chicago Midway

Wed 7/22

7:45 am-4:10 pm

2 stops7h 25m

Charleston

Sun 7/26

7:30 pm-8:45 pm

Nonstop2h 15m

$338

ChicagoCharleston

MDW - CHS

MDWCHS

Chicago Midway

Mon 7/20

7:45 pm-10:55 pm

Nonstop2h 10m

Charleston

Wed 7/22

10:45 am-4:55 pm

2 stops7h 10m

$338

ChicagoCharleston

MDW - CHS

MDWCHS

Chicago Midway

Wed 6/24

11:25 am-8:25 pm

2 stops8h 00m

Charleston

Sun 6/28

7:35 am-8:45 am

Nonstop2h 10m

$348

ChicagoCharleston

MDW - CHS

MDWCHS

Chicago Midway

Tue 6/30

11:25 am-8:25 pm

2 stops8h 00m

Charleston

Sun 7/5

7:05 am-1:05 pm

2 stops7h 00m

$353

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/30

Showing 1-10 of 21 resultsSorted by cheapest first
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 June.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust 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 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 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 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 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 June 4, 2026.

Unlike in the evening, when flights are generally more expensive, you can save up to 27% on flights from Chicago Midway Airport to Charleston by exploring options for tickets at noon.

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

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 June 4, 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
4,256 reviews

Comfort

8.0

Food

7.0

Crew

8.6

Overall

8.0

Entertainment

7.5

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

Walter,May 2026

LAS - BUR

Short but excellent flight. Everyone was friendly and professional it was a great flight!
Southwest
8.0
Very good
4,256 reviews
Southwest
8.0
Very good
4,256 reviews

Comfort

8.0

Food

7.0

Crew

8.6

Overall

8.0

Entertainment

7.5

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

Walter,May 2026

LAS - BUR

Short but excellent flight. Everyone was friendly and professional it was a great flight!

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 5h 50m. Southwest provides one of the quickest options available for as low as $282. Chicago Midway Airport and Charleston are separated by a distance of 745 mi.

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

    According to our current data, Southwest ($153), offers the cheapest pricing from Chicago Midway Airport to Charleston. Users have found that Southwest is 59% 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 $132. While the most popular route (Chicago Midway - Charleston) can be booked for $257 on average, our data indicates $292 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.

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
Goose Creek
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 June 4, 2026.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$153Average$405FlexibilityNo cancel feeOn-time63%

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