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$67+ 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 12/13. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — CHS
Oct 14 — Oct 211
Tue 10/14
Tue 10/21
1 adult, Economy
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Cheap 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 September 14, 2025.

Round-trip from

$236
(Kiwi.com)

One-way from

$67
(Southwest)

Popular in

September

Cheapest in

May

Average price

$460

Good round-trip deal

$153 or less

Good one-way deal

$128 or less
From Chicago Midway to Charleston
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One-way flight from Chicago Midway to Charleston
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Highest demand for flights based on searches. 3% potential increase in price ($14 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($10 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Price to beat on a round-trip flight from Chicago Midway to Charleston.
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Price to beat on a one-way flight from Chicago Midway to Charleston.
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Find 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 September 14, 2025.

This Kiwi.com deal was found by Cheapflights users on 9/11. 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 10/235:56 pmMDW - CHS
2 stops14h 10mMultiple Airlines
Mon 10/273:25 pmCHS - MDW
1 stop8h 38mMultiple Airlines
Deal found 9/11$236
This Southwest deal was found by Cheapflights users on 9/12. 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 11/116:40 amMDW - CHS
1 stop9h 25mSouthwest
Mon 11/177:20 pmCHS - MDW
1 stop4h 15mSouthwest
Deal found 9/12$243
This Southwest deal was found by Cheapflights users on 9/12. 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 12/65:30 pmMDW - CHS
Nonstop2h 05mSouthwest
Sun 12/77:15 pmCHS - MDW
Nonstop2h 15mSouthwest
Deal found 9/12$252
This Kiwi.com deal was found by Cheapflights users on 9/12. 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 11/136:26 pmMDW - CHS
1 stop21h 19mMultiple Airlines
Sun 11/1611:40 amCHS - MDW
1 stop13h 15mMultiple Airlines
Deal found 9/12$255
This Kiwi.com deal was found by Cheapflights users on 9/13. 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.
Sun 10/126:20 amMDW - CHS
2 stops15h 23mMultiple Airlines
Sat 10/258:10 pmCHS - MDW
1 stop16h 34mMultiple Airlines
Deal found 9/13$258
This Kiwi.com deal was found by Cheapflights users on 9/12. 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 10/305:56 pmMDW - CHS
1 stop23h 17mMultiple Airlines
Sun 11/210:11 amCHS - MDW
2 stops14h 44mMultiple Airlines
Deal found 9/12$260
This Kiwi.com deal was found by Cheapflights users on 9/13. 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 10/35:15 pmMDW - CHS
2 stops20h 14mMultiple Airlines
Sun 10/52:59 pmCHS - MDW
1 stop17h 24mMultiple Airlines
Deal found 9/13$266
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 11/108:00 amMDW - CHS
1 stop23h 37mMultiple Airlines
Fri 11/143:33 pmCHS - MDW
1 stop7h 37mMultiple Airlines
Deal found 9/14$268
This Southwest deal was found by Cheapflights users on 9/12. 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 9/306:05 pmMDW - CHS
Nonstop2h 10mSouthwest
Thu 10/26:15 pmCHS - MDW
Nonstop2h 10mSouthwest
Deal found 9/12$270

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 September 14, 2025.
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 11/11

6:40 am-5:05 pm

1 stop9h 25m

Charleston

Mon 11/17

7:20 pm-10:35 pm

1 stop4h 15m

$243

ChicagoCharleston

MDW - CHS

MDWCHS

Chicago Midway

Mon 10/20

12:48 pm-8:51 pm

1 stop7h 03m

Charleston

Wed 10/22

11:25 am-4:09 pm

1 stop5h 44m

$293

ChicagoCharleston

MDW - CHS

MDWCHS

Chicago Midway

Tue 11/18

1:15 pm-8:35 pm

1 stop6h 20m

Charleston

Wed 11/19

10:35 am-1:45 pm

1 stop4h 10m

$308

ChicagoCharleston

MDW - CHS

MDWCHS

Chicago Midway

Tue 11/11

5:34 pm-10:48 pm

1 stop4h 14m

Charleston

Tue 11/18

6:30 am-9:51 am

1 stop4h 21m

$313

ChicagoCharleston

MDW - CHS

MDWCHS

Chicago Midway

Fri 11/7

6:10 pm-10:55 pm

1 stop3h 45m

Charleston

Mon 11/10

7:15 pm-8:30 pm

Nonstop2h 15m

$313

ChicagoCharleston

MDW - CHS

MDWCHS

Chicago Midway

Mon 11/10

1:14 pm-6:13 pm

1 stop3h 59m

Charleston

Tue 11/18

6:30 am-9:51 am

1 stop4h 21m

$313

ChicagoCharleston

MDW - CHS

MDWCHS

Chicago Midway

Sat 10/18

6:00 am-11:49 am

1 stop4h 49m

Charleston

Tue 10/21

7:05 pm-10:14 pm

1 stop4h 09m

$313

ChicagoCharleston

MDW - CHS

MDWCHS

Chicago Midway

Wed 11/19

1:15 pm-8:35 pm

1 stop6h 20m

Charleston

Thu 11/20

6:00 am-9:55 am

1 stop4h 55m

$313

ChicagoCharleston

MDW - CHS

MDWCHS

Chicago Midway

Wed 11/12

6:00 am-11:46 am

1 stop4h 46m

Charleston

Tue 11/18

6:28 pm-11:32 pm

1 stop6h 04m

$313

ChicagoCharleston

MDW - CHS

MDWCHS

Chicago Midway

Sat 12/13

5:30 pm-8:35 pm

Nonstop2h 05m

$67

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/12

Showing 1-10 of 20 results
1
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The best insider tips for Chicago Midway Airport to Charleston flights

Snippets provided in this section are AI-generated based on a summarization of Cheapflights-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
Cheapflights partnered with top experts to bring you the best recommendations for your Chicago Midway Airport to Charleston trip
Airports
MDW

Use the Orange Line train for a quick, budget-friendly trip to MDW, taking less than 30 minutes from downtown Chicago.

Read more about MDWby Ramsey Qubein
CHS

For a quick ride to downtown Charleston, rideshare services are more convenient than taxis or buses from CHS.

Read more about CHSby Ramsey Qubein
Our travel experts
Ramsey Qubein

Ramsey Qubein

Expert on MDW and CHS

Ramsey Qubein

Ramsey Qubein

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

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, August is the cheapest month in which you can book a flight from Chicago Midway Airport to Charleston (average of $217). Flying from Chicago Midway Airport to Charleston in March is currently the most expensive (average of $335). 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 September 14, 2025.

Unlike in the morning, when flights are generally more expensive, you can save up to 15% on flights from Chicago Midway Airport to Charleston by exploring options for tickets in the evening.

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

Use this chart to determine the cheapest time to fly round-trip from Midway to Charleston. Price data was last updated on October 27, 2024.

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

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 September 14, 2025.
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
4,245 reviews

Overall

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Boarding

8.1

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,245 reviews
Southwest
8.0
Very good
4,245 reviews

Overall

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Boarding

8.1

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

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 7h 03m. Southwest provides one of the quickest options available for as low as $293. 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 ($257), 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 $85. While the most popular route (Chicago Midway - Charleston) can be booked for $143 on average, our data indicates $409 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, August is the cheapest month in which you can book a flight from Chicago Midway Airport to Charleston (average of $217). Flying from Chicago Midway Airport to Charleston in March is currently the most expensive (average of $335). 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
Summerville
Walterboro
Mount Pleasant
Isle of Palms
Santee
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 September 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$257Average$358FlexibilityNo cancel feeOn-time63%

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