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$78+ 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 12/15. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — CHS
Nov 28 — Dec 51
Fri 11/28
Fri 12/5
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 October 29, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$252
(Kiwi.com)

One-way from

$78
(Kiwi.com)

Popular in

December

Cheapest in

May

Average price

$384

Good round-trip deal

$474 or less
Provider with most accurate pricing for Chicago Midway-Charleston flight deals.
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Provider most trusted by Cheapflights users for Chicago Midway-Charleston flights.
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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. 5% potential increase in price ($20 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 October 2025
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Price to beat on a round-trip 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 October 29, 2025.

This Kiwi.com deal was found by Cheapflights users on 10/27. 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 11/106:15 amMDW - CHS
2 stops13h 08mMultiple Airlines
Thu 11/136:11 pmCHS - MDW
1 stop6h 44mMultiple Airlines
Deal found 10/27$252
This Kiwi.com deal was found by Cheapflights users on 10/27. 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 11/96:15 amMDW - CHS
2 stops13h 08mMultiple Airlines
Thu 11/136:11 pmCHS - MDW
1 stop6h 44mMultiple Airlines
Deal found 10/27$253
This Kiwi.com deal was found by Cheapflights users on 10/28. 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.
Sat 11/81:37 pmMDW - CHS
2 stops18h 00mMultiple Airlines
Tue 11/116:11 pmCHS - MDW
1 stop6h 44mMultiple Airlines
Deal found 10/28$256
This Kiwi.com deal was found by Cheapflights users on 10/27. 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 11/246:05 amMDW - CHS
2 stops10h 13mMultiple Airlines
Mon 12/16:13 pmCHS - MDW
1 stop19h 48mMultiple Airlines
Deal found 10/27$259
This Kiwi.com deal was found by Cheapflights users on 10/27. 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 11/26:26 pmMDW - CHS
1 stop12h 30mMultiple Airlines
Mon 12/16:13 pmCHS - MDW
1 stop19h 48mMultiple Airlines
Deal found 10/27$263
This Kiwi.com deal was found by Cheapflights users on 10/28. 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.
Sat 11/226:02 pmMDW - CHS
1 stop13h 35mMultiple Airlines
Mon 11/246:13 pmCHS - MDW
1 stop18h 29mMultiple Airlines
Deal found 10/28$267
This Southwest deal was found by Cheapflights users on 10/27. 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 11/225:30 pmMDW - CHS
Nonstop2h 05mSouthwest
Mon 11/247:15 pmCHS - MDW
Nonstop2h 15mSouthwest
Deal found 10/27$270
This Frontier deal was found by Cheapflights users on 10/28. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/228:29 pmMDW - CHS
1 stop10h 58mFrontier
Mon 11/249:12 amCHS - MDW
1 stop9h 54mFrontier
Deal found 10/28$271
This Southwest deal was found by Cheapflights users on 10/28. 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.
Thu 12/256:35 amMDW - CHS
1 stop4h 50mSouthwest
Wed 12/316:00 amCHS - MDW
1 stop4h 55mSouthwest
Deal found 10/28$281

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 October 29, 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 12/23

9:29 am-4:11 pm

1 stop5h 42m

Charleston

Thu 1/1

8:35 am-2:44 pm

1 stop7h 09m

$280

ChicagoCharleston

MDW - CHS

MDWCHS

Chicago Midway

Sat 11/22

5:30 pm-8:35 pm

Nonstop2h 05m

Charleston

Mon 11/24

8:20 pm-11:30 pm

1 stop4h 10m

$280

ChicagoCharleston

MDW - CHS

MDWCHS

Chicago Midway

Wed 12/17

9:20 am-5:05 pm

1 stop6h 45m

Charleston

Mon 12/22

8:00 pm-9:15 pm

Nonstop2h 15m

$289

ChicagoCharleston

MDW - CHS

MDWCHS

Chicago Midway

Thu 12/4

5:13 pm-11:50 pm

1 stop5h 37m

Charleston

Mon 12/8

9:00 am-11:55 am

1 stop3h 55m

$299

ChicagoCharleston

MDW - CHS

MDWCHS

Chicago Midway

Tue 12/2

12:55 pm-7:55 pm

1 stop6h 00m

Charleston

Sat 12/6

6:10 am-7:25 am

Nonstop2h 15m

$299

ChicagoCharleston

MDW - CHS

MDWCHS

Chicago Midway

Fri 11/14

5:57 pm-2:29 pm

1 stop19h 32m

Charleston

Mon 11/17

7:00 am-12:30 am

2 stops18h 30m

$304

ChicagoCharleston

MDW - CHS

MDWCHS

Chicago Midway

Thu 12/4

9:20 am-5:05 pm

1 stop6h 45m

Charleston

Fri 12/12

7:15 pm-8:30 pm

Nonstop2h 15m

$314

ChicagoCharleston

MDW - CHS

MDWCHS

Chicago Midway

Thu 12/4

6:00 am-11:45 am

1 stop4h 45m

Charleston

Fri 12/12

10:40 am-4:18 pm

1 stop6h 38m

$324

ChicagoCharleston

MDW - CHS

MDWCHS

Chicago Midway

Mon 1/12

10:18 am-8:38 am

1 stop21h 20m

$79

ChicagoCharleston

MDW - CHS

MDWCHS

Chicago Midway

Fri 11/7

12:14 pm-6:52 pm

1 stop5h 38m

$114

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/28

Showing 1-10 of 17 results
1
2

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 October.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice 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 eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Chicago Midway Airport-Charleston flight deals on Cheapflights vs. eDreams >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 eDreams the most. eDreams 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 $379). 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 October 29, 2025.

Unlike in the morning, when flights are generally more expensive, you can save up to 13% on flights from Chicago Midway Airport to Charleston by exploring options for tickets at noon.

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 Sunday at noon when fares are most often at their lowest. Monday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

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

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 October 29, 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
4,241 reviews

Crew

8.6

Overall

8.0

Food

7.0

Comfort

8.0

Boarding

8.1

Entertainment

7.5

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
4,241 reviews
Southwest
8.0
Very good
4,241 reviews

Crew

8.6

Overall

8.0

Food

7.0

Comfort

8.0

Boarding

8.1

Entertainment

7.5

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 2h 05m. Delta provides one of the quickest options available for as low as $280. 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 32% 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 $453. While the most popular route (Chicago Midway - Charleston) can be booked for $162 on average, our data indicates $645 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 $379). 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
Isle of Palms
Santee
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 October 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$245Average$359FlexibilityNo cancel feeOn-time63%

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