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Midway

$69+ 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 3/18. Fares are subject to change and may not be available on all flights or dates of travel.
CHS — MDW
Feb 25 — Mar 41
Wed 2/25
Wed 3/4
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 January 26, 2026.

This Kiwi.com deal was found by Cheapflights users on 1/25. 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 3/235:02 pm
CHS
-
MDW
1 stop21h 00m
Multiple Airlines
Thu 3/267:30 am
MDW
-
CHS
1 stop7h 30m
Multiple Airlines
Deal found 1/25$273
This Southwest deal was found by Cheapflights users on 1/25. 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 2/216:00 am
CHS
-
MDW
Nonstop2h 15m
Southwest
Mon 2/232:45 pm
MDW
-
CHS
Nonstop2h 00m
Southwest
Deal found 1/25$279
This Kiwi.com deal was found by Cheapflights users on 1/24. 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 5/43:35 pm
CHS
-
MDW
1 stop22h 25m
Multiple Airlines
Fri 5/84:09 pm
MDW
-
CHS
2 stops15h 39m
Multiple Airlines
Deal found 1/24$283
This Kiwi.com deal was found by Cheapflights users on 1/24. 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 3/123:11 pm
CHS
-
MDW
2 stops33h 40m
Multiple Airlines
Mon 3/169:51 pm
MDW
-
CHS
1 stop9h 47m
Multiple Airlines
Deal found 1/24$284
This Southwest deal was found by Cheapflights users on 1/25. 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 5/57:15 am
CHS
-
MDW
Nonstop2h 15m
Southwest
Sat 5/93:30 pm
MDW
-
CHS
Nonstop2h 05m
Southwest
Deal found 1/25$285
This Kiwi.com deal was found by Cheapflights users on 1/23. 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 3/133:21 pm
CHS
-
MDW
1 stop9h 30m
Multiple Airlines
Mon 3/169:51 pm
MDW
-
CHS
1 stop9h 47m
Multiple Airlines
Deal found 1/23$293
This Southwest deal was found by Cheapflights users on 1/25. 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 5/137:15 am
CHS
-
MDW
Nonstop2h 15m
Southwest
Sat 5/233:30 pm
MDW
-
CHS
Nonstop2h 05m
Southwest
Deal found 1/25$307

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 January 26, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

Expedia
3 stars

Round-trip from

$273
(Kiwi.com)

One-way from

$69
(Kiwi.com)

Popular in

April

Cheapest in

October

Average price

$426

Good round-trip deal

$339 or less

Good one-way deal

$185 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. 16% potential increase in price ($79 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 January 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 January 26, 2026.
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

Sat 2/21

6:00 am-7:15 am

Nonstop2h 15m

Chicago Midway

Mon 2/23

2:45 pm-5:45 pm

Nonstop2h 00m

$279

CharlestonChicago

CHS - MDW

CHSMDW

Charleston

Mon 3/23

8:07 am-10:19 pm

2 stops15h 12m

Chicago Midway

Thu 3/26

7:30 am-4:00 pm

1 stop7h 30m

$285

CharlestonChicago

CHS - MDW

CHSMDW

Charleston

Tue 2/24

7:30 am-11:59 am

1 stop5h 29m

Chicago Midway

Tue 3/3

12:45 pm-7:56 pm

1 stop6h 11m

$317

CharlestonChicago

CHS - MDW

CHSMDW

Charleston

Tue 3/3

1:45 pm-9:50 pm

1 stop9h 05m

Chicago Midway

Wed 3/4

9:50 am-3:50 pm

1 stop5h 00m

$317

CharlestonChicago

CHS - MDW

CHSMDW

Charleston

Wed 3/18

4:35 pm-5:55 pm

Nonstop2h 20m

Chicago Midway

Sat 3/21

4:35 pm-9:40 pm

1 stop4h 05m

$319

CharlestonChicago

CHS - MDW

CHSMDW

Charleston

Mon 3/23

5:45 pm-7:05 pm

Nonstop2h 20m

Chicago Midway

Thu 3/26

2:20 pm-12:15 am

1 stop8h 55m

$323

CharlestonChicago

CHS - MDW

CHSMDW

Charleston

Thu 2/19

8:30 am-11:59 am

1 stop4h 29m

Chicago Midway

Sat 2/21

9:34 am-5:38 pm

1 stop7h 04m

$325

CharlestonChicago

CHS - MDW

CHSMDW

Charleston

Fri 3/13

5:45 pm-7:05 pm

Nonstop2h 20m

Chicago Midway

Mon 3/16

4:05 pm-9:40 pm

1 stop4h 35m

$326

CharlestonChicago

CHS - MDW

CHSMDW

Charleston

Thu 3/12

5:45 pm-7:05 pm

Nonstop2h 20m

Chicago Midway

Mon 3/16

11:15 am-7:20 pm

2 stops7h 05m

$328

CharlestonChicago

CHS - MDW

CHSMDW

Charleston

Tue 2/24

11:40 am-6:35 pm

2 stops7h 55m

Chicago Midway

Tue 3/3

9:55 am-8:00 pm

2 stops9h 05m

$328

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/24

Showing 1-10 of 16 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 January.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*1 star
ExpediaPrice Accuracy2 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 Expedia the most. Expedia 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 $396). 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.

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 January 26, 2026.
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
4,268 reviews

Boarding

8.1

Food

7.0

Entertainment

7.5

Comfort

8.0

Overall

8.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Southwest
8.0
Very good
4,268 reviews
Southwest
8.0
Very good
4,268 reviews

Boarding

8.1

Food

7.0

Entertainment

7.5

Comfort

8.0

Overall

8.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Delta
7.9
Good
8,111 reviews
Southwest
8.0
Very good
4,268 reviews

Boarding

8.1

Food

7.0

Entertainment

7.5

Comfort

8.0

Overall

8.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

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 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 $333 for a flight from Charleston to Chicago Midway Airport. The cheapest flight overall is $169 while the most popular route, (Charleston - Chicago Midway) is currently priced at $247.

  • 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 $396). 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
Lansing
Merrillville
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 January 26, 2026.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$190Average$364FlexibilityNo cancel feeOn-time63%
DeltaCheapest$368Average$628FlexibilityNo cancel feeOn-timeN/A

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