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Midway

$102+ 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 5/20. Fares are subject to change and may not be available on all flights or dates of travel.
CHS — MDW
May 23 — May 301
Sat 5/23
Sat 5/30
1 adult, Economy
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Cheap 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 April 23, 2026.

This Southwest deal was found by Cheapflights users on 4/21. 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.
Thu 6/44:45 pm
CHS
-
MDW
1 stop3h 50m
Southwest
Sat 6/66:10 pm
MDW
-
CHS
Nonstop2h 05m
Southwest
Deal found 4/21$272
This Southwest deal was found by Cheapflights users on 4/20. 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.
Wed 6/101:50 pm
CHS
-
MDW
1 stop6h 15m
Southwest
Sat 6/136:10 pm
MDW
-
CHS
Nonstop2h 05m
Southwest
Deal found 4/20$273
This Southwest deal was found by Cheapflights users on 4/21. 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.
Wed 9/235:10 pm
CHS
-
MDW
1 stop4h 35m
Southwest
Fri 9/258:05 am
MDW
-
CHS
Nonstop2h 20m
Southwest
Deal found 4/21$275
This Southwest deal was found by Cheapflights users on 4/21. 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.
Thu 6/48:00 am
CHS
-
MDW
Nonstop2h 15m
Southwest
Mon 6/87:45 pm
MDW
-
CHS
Nonstop2h 05m
Southwest
Deal found 4/21$276
This Southwest deal was found by Cheapflights users on 4/21. 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.
Wed 5/207:15 am
CHS
-
MDW
Nonstop2h 15m
Southwest
Mon 5/256:50 pm
MDW
-
CHS
Nonstop2h 05m
Southwest
Deal found 4/21$280
This Southwest deal was found by Cheapflights users on 4/22. 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 6/107:00 am
CHS
-
MDW
Nonstop2h 10m
Southwest
Mon 6/158:05 am
MDW
-
CHS
Nonstop2h 20m
Southwest
Deal found 4/22$281
This Southwest deal was found by Cheapflights users on 4/22. 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.
Mon 6/13:50 pm
CHS
-
MDW
1 stop9h 05m
Southwest
Thu 6/47:45 pm
MDW
-
CHS
Nonstop2h 05m
Southwest
Deal found 4/22$285

Find 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 April 23, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$272
(Southwest)

One-way from

$102
(Southwest)

Popular in

May

Cheapest in

October

Average price

$302

Good round-trip deal

$389 or less

Good one-way deal

$193 or less
Provider with most accurate pricing for Charleston-Chicago Midway flight deals.
Search Deals
Provider most trusted by Cheapflights users for Charleston-Chicago Midway flights.
Search Deals
From Charleston to Chicago Midway
Search Deals
One-way flight from Charleston to Chicago Midway
Search Deals
Highest demand for flights based on searches. 4% potential increase in price ($21 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($17 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 2026
Search Deals
Price to beat on a round-trip flight from Charleston to Chicago Midway.
Search Deals
Price to beat on a one-way flight from Charleston to Chicago Midway.
Search Deals

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 April 23, 2026.
Use the filters below to find and compare flights from Charleston to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

CharlestonChicago

CHS - MDW

CHSMDW

Charleston

Fri 6/5

4:45 pm-7:35 pm

1 stop3h 50m

Chicago Midway

Mon 6/8

7:45 pm-10:50 pm

Nonstop2h 05m

$310

CharlestonChicago

CHS - MDW

CHSMDW

Charleston

Fri 8/21

7:10 am-12:30 pm

1 stop6h 20m

Chicago Midway

Mon 8/24

10:35 am-4:54 pm

1 stop5h 19m

$319

CharlestonChicago

CHS - MDW

CHSMDW

Charleston

Sun 8/16

5:55 pm-9:46 pm

1 stop4h 51m

Chicago Midway

Mon 8/17

1:00 pm-5:58 pm

1 stop3h 58m

$336

CharlestonChicago

CHS - MDW

CHSMDW

Charleston

Wed 7/29

6:15 am-10:03 am

1 stop4h 48m

Chicago Midway

Sat 8/1

6:05 am-11:54 am

1 stop4h 49m

$341

CharlestonChicago

CHS - MDW

CHSMDW

Charleston

Wed 7/22

11:18 am-4:15 pm

1 stop5h 57m

Chicago Midway

Sat 7/25

10:55 am-3:53 pm

1 stop3h 58m

$341

CharlestonChicago

CHS - MDW

CHSMDW

Charleston

Sat 5/30

4:55 pm-9:09 pm

1 stop5h 14m

Chicago Midway

Sun 5/31

6:23 am-12:10 pm

1 stop4h 47m

$348

CharlestonChicago

CHS - MDW

CHSMDW

Charleston

Wed 8/5

6:45 am-3:25 pm

2 stops9h 40m

Chicago Midway

Sun 8/9

6:05 pm-9:15 pm

Nonstop2h 10m

$354
Quickest round-trip

CharlestonChicago

CHS - MDW

CHSMDW

Charleston

Fri 8/7

6:30 pm-7:40 pm

Nonstop2h 10m

Chicago Midway

Sun 8/9

6:05 pm-9:15 pm

Nonstop2h 10m

$357

CharlestonChicago

CHS - MDW

CHSMDW

Charleston

Mon 7/27

1:05 pm-4:15 pm

1 stop4h 10m

Chicago Midway

Wed 7/29

5:10 pm-12:26 am

1 stop6h 16m

$359

CharlestonChicago

CHS - MDW

CHSMDW

Charleston

Fri 5/29

5:45 pm-11:55 pm

1 stop7h 10m

Chicago Midway

Sun 5/31

5:15 am-1:25 pm

1 stop7h 10m

$361

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/20

Showing 1-10 of 24 resultsSorted by cheapest first
1
2
3

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 April.
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 Charleston-Chicago Midway Airport flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Charleston-Chicago Midway Airport flight deals on Cheapflights vs. FlightHub >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 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 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 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 April 23, 2026.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Charleston to Chicago Midway Airport as you normally would.

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

The best insider tips for Charleston to Chicago Midway Airport 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 Charleston to Chicago Midway Airport 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 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 April 23, 2026.
See what other customers who have flown with Southwest 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
4,327 reviews

Entertainment

7.5

Comfort

8.0

Boarding

8.1

Food

7.0

Crew

8.6

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Southwest
8.0
Very good
4,327 reviews
Southwest
8.0
Very good
4,327 reviews

Entertainment

7.5

Comfort

8.0

Boarding

8.1

Food

7.0

Crew

8.6

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

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 0 outbound flights to Chicago Midway per day. You should also have plenty of airline options to choose from since 1 airline has 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 and Delta can get you from Charleston to Chicago Midway Airport in just under 3h 50m. Your travel time can differ by up to 2h 30m. Charleston and Chicago Midway Airport are separated by a distance of 745 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What is the cheapest airline to fly 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. You may be able to fly from Charleston to Chicago Midway Airport for 53% less than the average price by searching for this airline.

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

    On average you can expect to pay $354 for a flight from Charleston to Chicago Midway Airport. The cheapest flight overall is $118 while the most popular route, (Charleston - Chicago Midway) is currently priced at $227.

  • 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.

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
Benton Harbor
Lansing
Merrillville
Hammond
Porter

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Top airline flying from Charleston to Midway

Discover the top airline 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 April 23, 2026.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$190Average$337FlexibilityNo cancel feeOn-time63%

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