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$67+ 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 11/8. Fares are subject to change and may not be available on all flights or dates of travel.
CHS — MDW
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
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 September 11, 2025.

Round-trip from

$208
(Kiwi.com)

One-way from

$67
(Southwest)

Popular in

April

Cheapest in

July

Average price

$400

Good round-trip deal

$306 or less

Good one-way deal

$209 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 ($65 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($17 potential savings vs. average RT price).
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Average for round-trip flights in September 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 September 11, 2025.

This Kiwi.com deal was found by Cheapflights users on 9/10. 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 10/212:08 pmCHS - MDW
2 stops12h 33mMultiple Airlines
Sun 10/56:21 amMDW - CHS
1 stop7h 07mMultiple Airlines
Deal found 9/10$208
This Southwest deal was found by Cheapflights users on 9/9. 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 11/137:15 pmCHS - MDW
Nonstop2h 15mSouthwest
Fri 11/149:35 amMDW - CHS
1 stop8h 55mSouthwest
Deal found 9/9$236
This Southwest deal was found by Cheapflights users on 9/10. 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 11/37:20 pmCHS - MDW
1 stop4h 15mSouthwest
Tue 11/412:55 pmMDW - CHS
1 stop6h 00mSouthwest
Deal found 9/10$238
This Southwest deal was found by Cheapflights users on 9/10. 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 10/26:15 pmCHS - MDW
Nonstop2h 10mSouthwest
Sat 10/412:15 pmMDW - CHS
1 stop8h 00mSouthwest
Deal found 9/10$244
This Kiwi.com deal was found by Cheapflights users on 9/10. 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 10/310:10 amCHS - MDW
2 stops14h 31mMultiple Airlines
Sun 10/56:21 amMDW - CHS
1 stop7h 07mMultiple Airlines
Deal found 9/10$245
This Southwest deal was found by Cheapflights users on 9/9. 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 10/213:25 pmCHS - MDW
2 stops8h 00mSouthwest
Sat 10/258:20 amMDW - CHS
2 stops7h 35mSouthwest
Deal found 9/9$256
This Southwest deal was found by Cheapflights users on 9/9. 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 10/85:35 amCHS - MDW
Nonstop2h 10mSouthwest
Sun 10/129:05 pmMDW - CHS
Nonstop2h 05mSouthwest
Deal found 9/9$265
This Southwest deal was found by Cheapflights users on 9/10. 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 11/268:00 pmCHS - MDW
Nonstop2h 15mSouthwest
Thu 11/276:20 amMDW - CHS
1 stop7h 35mSouthwest
Deal found 9/10$269

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 September 11, 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

Mon 11/3

7:20 pm-10:35 pm

1 stop4h 15m

Chicago Midway

Tue 11/4

12:55 pm-7:55 pm

1 stop6h 00m

$238

CharlestonChicago

CHS - MDW

CHSMDW

Charleston

Tue 10/21

3:25 pm-10:25 pm

2 stops8h 00m

Chicago Midway

Sat 10/25

8:20 am-4:55 pm

2 stops7h 35m

$256

CharlestonChicago

CHS - MDW

CHSMDW

Charleston

Thu 1/22

4:50 pm-10:05 pm

1 stop6h 15m

Chicago Midway

Mon 1/26

10:00 am-8:50 pm

2 stops9h 50m

$265

CharlestonChicago

CHS - MDW

CHSMDW

Charleston

Wed 10/8

5:35 am-6:45 am

Nonstop2h 10m

Chicago Midway

Sun 10/12

9:05 pm-12:10 am

Nonstop2h 05m

$265

CharlestonChicago

CHS - MDW

CHSMDW

Charleston

Thu 11/13

7:15 pm-8:30 pm

Nonstop2h 15m

Chicago Midway

Fri 11/14

1:40 pm-4:40 pm

Nonstop2h 00m

$275

CharlestonChicago

CHS - MDW

CHSMDW

Charleston

Wed 11/26

5:10 am-2:05 pm

2 stops9h 55m

Chicago Midway

Thu 11/27

6:20 am-2:55 pm

1 stop7h 35m

$284

CharlestonChicago

CHS - MDW

CHSMDW

Charleston

Sat 11/8

6:10 am-7:25 am

Nonstop2h 15m

Chicago Midway

Sun 11/9

5:05 am-2:10 pm

1 stop8h 05m

$285

CharlestonChicago

CHS - MDW

CHSMDW

Charleston

Sat 10/25

8:05 am-11:40 am

1 stop4h 35m

Chicago Midway

Sun 10/26

9:05 pm-12:10 am

Nonstop2h 05m

$292

CharlestonChicago

CHS - MDW

CHSMDW

Charleston

Thu 12/11

5:25 am-9:54 am

1 stop5h 29m

Chicago Midway

Sat 12/13

9:59 am-4:38 pm

1 stop5h 39m

$293

CharlestonChicago

CHS - MDW

CHSMDW

Charleston

Wed 12/10

7:20 pm-10:35 pm

1 stop4h 15m

$77

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/11

Showing 1-10 of 20 results
1
2

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 September 11, 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 evening tend to be the most expensive. A flight at noon could potentially save you up to 20% 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 September 11, 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
4,248 reviews

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Crew

8.6

Overall

8.0

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
4,248 reviews
Southwest
8.0
Very good
4,248 reviews

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Crew

8.6

Overall

8.0

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
8.0
Very good
7,960 reviews
Southwest
8.0
Very good
4,248 reviews

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Crew

8.6

Overall

8.0

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 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 4h 15m. Your travel time can differ by up to . Charleston and Chicago Midway Airport are separated by a distance of 745 mi.

  • 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 54% 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 $360 for a flight from Charleston to Chicago Midway Airport. The cheapest flight overall is $124 while the most popular route, (Charleston - Chicago Midway) is currently priced at $149.

  • 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 Chicago Midway Airport?

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

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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 September 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$190Average$388FlexibilityNo cancel feeOn-time63%
DeltaCheapest$368Average$628FlexibilityNo cancel feeOn-timeN/A

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