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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 5/12. Fares are subject to change and may not be available on all flights or dates of travel.
CHS — MDW
Feb 11 — Feb 181
Tue 2/11
Tue 2/18
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 February 6, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$322
(Southwest)

One-way from

$91
(Trip.com)

Popular in

May

Cheapest in

September

Average price

$356

Good round-trip deal

$349 or less

Good one-way deal

$191 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
Search Deals
Highest demand for flights based on searches. 11% potential increase in price ($53 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease ($23 potential savings vs. average RT price).
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Average for round-trip flights in February 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 February 6, 2025.

This Southwest deal was found by Cheapflights users on 2/6. 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 3/149:30 pmCHS - MDW
1 stop3h 50mSouthwest
Tue 3/181:50 pmMDW - CHS
1 stop6h 50mSouthwest
Deal found 2/6$322
This Delta deal was found by Cheapflights users on 2/5. 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.
Mon 3/105:35 amCHS - MDW
1 stop4h 34mDelta
Mon 3/174:59 pmMDW - CHS
1 stop5h 58mDelta
Deal found 2/5$329
This Mytrip deal was found by Cheapflights users on 2/6. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/267:00 amCHS - MDW
2 stops25h 15mMultiple Airlines
Mon 6/308:05 amMDW - CHS
3 stops32h 58mMultiple Airlines
Deal found 2/6$927

Find flights from Charleston to Midway within your budget

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 February 6, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

CharlestonChicago

CHS - MDW

CHSMDW

Charleston

Fri 3/14

9:30 pm-12:20 am

1 stop3h 50m

Chicago Midway

Tue 3/18

1:50 pm-9:40 pm

1 stop6h 50m

$322

CharlestonChicago

CHS - MDW

CHSMDW

Charleston

Mon 3/10

5:35 am-9:09 am

1 stop4h 34m

Chicago Midway

Mon 3/17

4:59 pm-11:57 pm

1 stop5h 58m

$329

CharlestonChicago

CHS - MDW

CHSMDW

Charleston

Thu 6/26

7:00 am-7:15 am

2 stops25h 15m

Chicago Midway

Mon 6/30

8:05 am-6:03 pm

3 stops32h 58m

$927

CharlestonChicago

CHS - MDW

CHSMDW

Charleston

Mon 5/12

10:01 am-5:28 pm

1 stop8h 27m

$91

CharlestonChicago

CHS - MDW

CHSMDW

Charleston

Tue 2/18

8:10 am-9:30 am

Nonstop2h 20m

$140

CharlestonChicago

CHS - MDW

CHSMDW

Charleston

Thu 3/6

10:28 am-4:20 pm

1 stop6h 52m

$150

CharlestonChicago

CHS - MDW

CHSMDW

Charleston

Sun 3/9

7:05 am-7:50 am

2 stops25h 45m

$167

CharlestonChicago

CHS - MDW

CHSMDW

Charleston

Sun 5/11

3:56 pm-7:45 am

2 stops16h 49m

$238

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/5

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 February.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 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 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.

Travel insights for flights from Charleston to Midway

Get recent, data-driven insights about flights from Charleston to Midway including ideal travel times, pricing trends, and more.

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 February 6, 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 30% on airfare.

Rainfall in Midway by month

Plan your trip to Midway by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago Midway Airport ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago Midway Airport when rainfall is around 1.7 in.

Temperature in Midway by month

Plan your trip to Midway by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago Midway Airport, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 February 6, 2025.
To help decide which airline to fly from Charleston to Chicago, see what other customers have to say about Southwest, Delta and Allegiant Air. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,549 reviews

Entertainment

7.7

Overall

8.1

Boarding

8.2

Comfort

8.1

Crew

8.7

Food

7.1

Reviews

1 / 20

6.0
Good

Lauren,Dec 2024

MCI - DCA

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Southwest
8.1
Very good
4,549 reviews
Southwest
8.1
Very good
4,549 reviews

Entertainment

7.7

Overall

8.1

Boarding

8.2

Comfort

8.1

Crew

8.7

Food

7.1

Reviews

1 / 20

6.0
Good

Lauren,Dec 2024

MCI - DCA

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Delta
8.0
Very good
8,388 reviews
Southwest
8.1
Very good
4,549 reviews

Entertainment

7.7

Overall

8.1

Boarding

8.2

Comfort

8.1

Crew

8.7

Food

7.1

Reviews

1 / 20

6.0
Good

Lauren,Dec 2024

MCI - DCA

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Allegiant Air
7.3
Good
782 reviews
Southwest
8.1
Very good
4,549 reviews

Entertainment

7.7

Overall

8.1

Boarding

8.2

Comfort

8.1

Crew

8.7

Food

7.1

Reviews

1 / 20

6.0
Good

Lauren,Dec 2024

MCI - DCA

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Frontier
6.0
Okay
3,410 reviews
Southwest
8.1
Very good
4,549 reviews

Entertainment

7.7

Overall

8.1

Boarding

8.2

Comfort

8.1

Crew

8.7

Food

7.1

Reviews

1 / 20

6.0
Good

Lauren,Dec 2024

MCI - DCA

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

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.

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

    Currently priced at $322, 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 $345. You may be able to fly from Charleston to Chicago Midway Airport for 24% 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 Frontier, with whom users have recently found tickets for as low as $91. However, be on the lookout for offers from Southwest 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 $290 for a flight from Charleston to Chicago Midway Airport. The cheapest flight overall is $179 while the most popular route, (Charleston - Chicago Midway) is currently priced at $279.

  • 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
New Buffalo
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
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 February 6, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$256Average$432FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$308Average$440FlexibilityNo cancel feeOn-time63%
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