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$91+ 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 9/30. Fares are subject to change and may not be available on all flights or dates of travel.
CHS — MDW
Jul 5 — Jul 121
Sat 7/5
Sat 7/12
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 June 30, 2025.

Round-trip from

$238
(Southwest)

One-way from

$91
(Southwest)

Popular in

April

Cheapest in

September

Average price

$389

Good round-trip deal

$310 or less

Good one-way deal

$139 or less
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. 13% potential increase in price ($66 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($17 potential savings vs. average RT price).
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Average for round-trip flights in June 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 June 30, 2025.

This Southwest deal was found by Cheapflights users on 6/29. 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.
Fri 11/147:15 pmCHS - MDW
Nonstop2h 15mSouthwest
Mon 11/175:35 amMDW - CHS
1 stop5h 50mSouthwest
Deal found 6/29$238
This Delta deal was found by Cheapflights users on 6/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/134:44 pmCHS - MDW
1 stop6h 00mDelta
Sun 8/176:04 amMDW - CHS
1 stop4h 46mDelta
Deal found 6/28$270
This CheapOair deal was found by Cheapflights users on 6/28. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/43:26 pmCHS - MDW
1 stop16h 50mFrontier
Sun 9/78:15 amMDW - CHS
1 stop5h 16mFrontier
Deal found 6/28$293

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 June 30, 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

7:15 pm-8:30 pm

Nonstop2h 15m

Chicago Midway

Mon 11/17

5:35 am-12:25 pm

1 stop5h 50m

$238

CharlestonChicago

CHS - MDW

CHSMDW

Charleston

Wed 8/13

5:15 am-9:36 am

1 stop5h 21m

Chicago Midway

Sun 8/17

6:04 am-11:50 am

1 stop4h 46m

$270

CharlestonChicago

CHS - MDW

CHSMDW

Charleston

Thu 9/4

3:26 pm-7:16 am

1 stop16h 50m

Chicago Midway

Sun 9/7

8:15 am-2:31 pm

1 stop5h 16m

$293

CharlestonChicago

CHS - MDW

CHSMDW

Charleston

Tue 9/30

6:35 am-7:40 am

Nonstop2h 05m

$91

CharlestonChicago

CHS - MDW

CHSMDW

Charleston

Thu 9/25

8:10 pm-4:43 pm

2 stops21h 33m

$140

CharlestonChicago

CHS - MDW

CHSMDW

Charleston

Fri 8/8

9:05 am-11:51 pm

1 stop15h 46m

$151

CharlestonChicago

CHS - MDW

CHSMDW

Charleston

Wed 7/30

6:25 am-9:45 am

1 stop4h 20m

$160

CharlestonChicago

CHS - MDW

CHSMDW

Charleston

Sun 8/3

3:26 pm-8:22 am

2 stops17h 56m

$198

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/30

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

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 $160). Flying from Charleston to Chicago Midway Airport in November is currently the most expensive (average of $249). 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 June 30, 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 at noon could potentially save you up to 16% on airfare.

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 June 30, 2025.
See what other customers who have flown with Southwest, Delta, and Allegiant Air 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
4,278 reviews

Food

7.0

Crew

8.6

Entertainment

7.6

Overall

8.0

Boarding

8.2

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Southwest
8.0
Very good
4,278 reviews
Southwest
8.0
Very good
4,278 reviews

Food

7.0

Crew

8.6

Entertainment

7.6

Overall

8.0

Boarding

8.2

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Delta
8.0
Very good
7,973 reviews
Southwest
8.0
Very good
4,278 reviews

Food

7.0

Crew

8.6

Entertainment

7.6

Overall

8.0

Boarding

8.2

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Allegiant Air
7.2
Good
711 reviews
Southwest
8.0
Very good
4,278 reviews

Food

7.0

Crew

8.6

Entertainment

7.6

Overall

8.0

Boarding

8.2

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Frontier
5.9
Fair
3,290 reviews
Southwest
8.0
Very good
4,278 reviews

Food

7.0

Crew

8.6

Entertainment

7.6

Overall

8.0

Boarding

8.2

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

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 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.

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

    Currently priced at $238, 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. Search Cheapflights for deals from Delta and Frontier - these airlines can fly you to your destination from $270 and $293, respectively. You may be able to fly from Charleston to Chicago Midway Airport for 43% less than the average price by searching for these airlines.

  • What are the cheapest airlines to fly from Charleston to Chicago Midway Airport one-way?

    The cheapest airline one-way is Southwest, with whom users have recently found tickets for as low as $91. However, be on the lookout for offers from Frontier and Delta, as they are both options that can get you from Charleston to Chicago Midway Airport for a low price.

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

    On average you can expect to pay $278 for a flight from Charleston to Chicago Midway Airport. The cheapest flight overall is $88 while the most popular route, (Charleston - Chicago Midway) is currently priced at $181.

  • 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 $160). Flying from Charleston to Chicago Midway Airport in November is currently the most expensive (average of $249). 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
Merrillville
Lansing
Benton Harbor
Porter
Hammond
Valparaiso
Chesterton

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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 June 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$279Average$407FlexibilityNo cancel feeOn-time63%

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