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$66+ Cheap flights from Charleston (CHS) to Midway (MDW)

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 11/18. Fares are subject to change and may not be available on all flights or dates of travel.
CHS — MDW
Nov 27 — Dec 41
Thu 11/27
Thu 12/4
1 adult, Economy
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Cheap flight deals from Charleston to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Charleston (CHS) to Midway (MDW). 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 28, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$211
(Kiwi.com)

One-way from

$66
(Trip.com)

Popular in

April

Cheapest in

July

Average price

$294

Good round-trip deal

$329 or less

Good one-way deal

$308 or less
Provider with most accurate pricing for Charleston-Chicago Midway flight deals.
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Provider most trusted by Cheapflights users for Charleston-Chicago Midway flights.
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From Charleston to Chicago Midway
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One-way flight from Charleston to Chicago Midway
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Highest demand for flights based on searches. 16% potential increase in price ($79 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($18 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 Charleston to Chicago Midway.
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Price to beat on a one-way flight from Charleston to Chicago Midway.
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Find flight deals from Charleston to Midway

Cheapest flights from Charleston to Midway
Explore the most affordable flight options available from Charleston to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 28, 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.
Wed 11/266:15 pmCHS - MDW
1 stop18h 27mMultiple Airlines
Wed 12/32:49 pmMDW - CHS
2 stops19h 11mMultiple Airlines
Deal found 10/27$211
This Kiwi.com deal was found by Cheapflights users on 10/26. 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 11/143:33 pmCHS - MDW
1 stop19h 53mMultiple Airlines
Mon 11/176:06 pmMDW - CHS
1 stop14h 22mMultiple Airlines
Deal found 10/26$225
This Kiwi.com deal was found by Cheapflights users on 10/26. 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 11/143:33 pmCHS - MDW
1 stop19h 53mMultiple Airlines
Sun 11/166:06 pmMDW - CHS
1 stop19h 18mMultiple Airlines
Deal found 10/26$236
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.
Wed 11/128:10 pmCHS - MDW
2 stops19h 23mMultiple Airlines
Sun 11/166:26 pmMDW - CHS
1 stop12h 30mMultiple Airlines
Deal found 10/28$239
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.
Sat 11/226:15 pmCHS - MDW
1 stop18h 27mMultiple Airlines
Mon 11/246:05 amMDW - CHS
2 stops10h 13mMultiple Airlines
Deal found 10/27$240
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 11/36:11 pmCHS - MDW
2 stops18h 27mMultiple Airlines
Tue 11/46:26 pmMDW - CHS
1 stop21h 40mMultiple Airlines
Deal found 10/27$247
This Kiwi.com deal was found by Cheapflights users on 10/26. 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 11/136:11 pmCHS - MDW
1 stop6h 44mMultiple Airlines
Mon 11/176:15 amMDW - CHS
2 stops13h 08mMultiple Airlines
Deal found 10/26$259
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.
Fri 11/213:33 pmCHS - MDW
1 stop8h 56mMultiple Airlines
Sun 11/236:20 amMDW - CHS
1 stop24h 06mMultiple Airlines
Deal found 10/28$270
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 11/227:20 pmCHS - MDW
Nonstop2h 15mSouthwest
Mon 11/242:55 pmMDW - CHS
1 stop7h 00mSouthwest
Deal found 10/27$280
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.
Sat 11/88:10 pmCHS - MDW
2 stops15h 16mMultiple Airlines
Mon 11/108:00 amMDW - CHS
1 stop23h 37mMultiple Airlines
Deal found 10/27$284
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 12/66:10 amCHS - MDW
Nonstop2h 15mSouthwest
Mon 12/81:20 pmMDW - CHS
1 stop6h 15mSouthwest
Deal found 10/27$289

Cheapflights Fare Finder

 
Customize your flight search to find flights from Charleston to Midway 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 28, 2025.
Use the filters below to find and compare flights from Charleston to Chicago Midway Airport that are best for you.

Fly from

Charleston

Fly to

Midway

Route

Depart

Return

Price

CharlestonChicago

CHS - MDW

CHSMDW

Charleston

Fri 11/14

3:33 pm-10:26 am

1 stop19h 53m

Chicago Midway

Sun 11/16

6:06 pm-2:24 pm

1 stop19h 18m

$236

CharlestonChicago

CHS - MDW

CHSMDW

Charleston

Sat 12/6

6:10 am-7:25 am

Nonstop2h 15m

Chicago Midway

Mon 12/8

1:20 pm-8:35 pm

1 stop6h 15m

$289

CharlestonChicago

CHS - MDW

CHSMDW

Charleston

Tue 12/30

9:08 pm-10:12 pm

2 stops26h 04m

Chicago Midway

Sun 1/4

2:16 pm-8:57 am

1 stop17h 41m

$295

CharlestonChicago

CHS - MDW

CHSMDW

Charleston

Thu 12/11

6:30 am-9:54 am

1 stop4h 24m

Chicago Midway

Sat 12/13

4:29 pm-9:45 pm

1 stop4h 16m

$299

CharlestonChicago

CHS - MDW

CHSMDW

Charleston

Tue 3/3

5:30 am-9:56 am

1 stop5h 26m

Chicago Midway

Wed 3/4

1:05 pm-8:40 pm

1 stop6h 35m

$299

CharlestonChicago

CHS - MDW

CHSMDW

Charleston

Tue 1/13

10:25 am-4:31 pm

1 stop7h 06m

Chicago Midway

Mon 1/26

9:34 am-5:43 pm

1 stop7h 09m

$299

CharlestonChicago

CHS - MDW

CHSMDW

Charleston

Tue 11/25

5:10 am-10:55 am

1 stop6h 45m

Chicago Midway

Thu 11/27

6:10 am-3:20 pm

1 stop8h 10m

$305

CharlestonChicago

CHS - MDW

CHSMDW

Charleston

Wed 12/3

6:15 pm-6:08 pm

2 stops24h 53m

$100

CharlestonChicago

CHS - MDW

CHSMDW

Charleston

Thu 1/29

11:40 am-11:25 pm

2 stops36h 45m

$100

CharlestonChicago

CHS - MDW

CHSMDW

Charleston

Mon 11/10

7:00 am-11:38 am

2 stops29h 38m

$115

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/27

Showing 1-10 of 17 results
1
2

Compare providers for flights from Charleston to Midway

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 Charleston to Midway in October.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*1 star
ExpediaPrice Accuracy2 starsTrust Score*3 stars
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 Charleston-Chicago Midway Airport flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Charleston-Chicago Midway Airport flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Charleston-Chicago Midway Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Charleston-Chicago Midway Airport 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 Charleston-Chicago Midway Airport 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 Charleston to Midway

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

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

Currently, April is the cheapest month in which you can book a flight from Charleston to Chicago Midway Airport (average of $76). Flying from Charleston to Chicago Midway Airport in December is currently the most expensive (average of $313). 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 CHS to MDW?

Find hourly flight availability from Charleston to Midway. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated October 28, 2025.

One of the essential ways to save on airfare from Charleston to Chicago Midway Airport is to remain as flexible as possible. Flights that are in the morning tend to be the most expensive. A flight in the afternoon could potentially save you up to 26% on airfare.

The best insider tips for Charleston to Chicago Midway Airport 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 Charleston to Chicago Midway Airport trip
Airports
CHS

Expect long security lines during early-morning hours when most flights depart. Arrive early to ensure a smooth departure.

Read more about CHSby Ramsey Qubein
MDW

Use the 'L' train for a quick, affordable ride to downtown Chicago, taking less than 30 minutes from MDW.

Read more about MDWby 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 Midway

Get insights into the airlines that provide service to Midway. 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 Midway. Reviews last updated October 28, 2025.
See what other customers who have flown with Southwest and Delta from Charleston to Chicago Midway Airport 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
4,240 reviews

Crew

8.6

Boarding

8.1

Comfort

8.0

Overall

8.0

Entertainment

7.5

Food

7.0

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
4,240 reviews
Southwest
8.0
Very good
4,240 reviews

Crew

8.6

Boarding

8.1

Comfort

8.0

Overall

8.0

Entertainment

7.5

Food

7.0

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
Delta
7.9
Good
7,994 reviews
Southwest
8.0
Very good
4,240 reviews

Crew

8.6

Boarding

8.1

Comfort

8.0

Overall

8.0

Entertainment

7.5

Food

7.0

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 Charleston to Midway. 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 from for flights from Charleston to Chicago Midway?

    Charleston (CHS) is the airport you will fly out of if you book a flight from Charleston to Chicago Midway. You should not have trouble finding flights to Chicago Midway from Charleston; the airport handles an average of 1 outbound flight to Chicago Midway per day. You should also have plenty of airline options to choose from since 2 airlines have flights from the Charleston airport to Chicago Midway. It is only a 10.2 mi journey to Charleston (CHS) from Charleston’s city center.

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

    Southwest can get you from Charleston to Chicago Midway Airport in just under 2h 15m. Your travel time will be generally consistent. Charleston and Chicago Midway Airport are separated by a distance of 745 mi. Most flights are nonstop.

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

    Currently priced at $190, Southwest will fly you from Charleston to Chicago Midway Airport and back. In addition to Southwest, many other airlines offer competitively priced options for your trip. Check Cheapflights for deals on Delta for as low as $368. You may be able to fly from Charleston to Chicago Midway Airport for 53% less than the average price by searching for these airlines.

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

    On average you can expect to pay $341 for a flight from Charleston to Chicago Midway Airport. The cheapest flight overall is $229 while the most popular route, (Charleston - Chicago Midway) is currently priced at $185.

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

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

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

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

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

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

    Currently, April is the cheapest month in which you can book a flight from Charleston to Chicago Midway Airport (average of $76). Flying from Charleston to Chicago Midway Airport in December is currently the most expensive (average of $313). 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 Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Porter
Benton Harbor

Browse thousands of different options on Cheapflights for your next trip

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Top 2 airlines flying from Charleston to Midway

Discover the top 2 airlines that operate flights from Charleston to Midway. 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 28, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$190Average$366FlexibilityNo cancel feeOn-time63%
DeltaCheapest$368Average$628FlexibilityNo cancel feeOn-timeN/A

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