$116 Cheap Flights from Chicago (MDW) to Charleston (CHS)

View $116 flight on Fri, Oct 31, 2025Opens in a new window

Popular airlines from Chicago Midway Airport (MDW) to Charleston Intl. Airport (CHS)

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Cheap Flights from Chicago to Charleston (MDW-CHS)

Prices were available within the past 7 days and start at $116 for one-way flights and $233 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Southwest Airlines
Tue, Oct 21 - Wed, Oct 22
MDW
Chicago
CHS
Charleston
$233 Roundtrip, found 4 days ago
$233
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Tue, Oct 21 from Chicago to Charleston, returning Wed, Oct 22, priced at $233 found 4 days ago
Southwest Airlines
Mon, Oct 27 - Tue, Oct 28
MDW
Chicago
CHS
Charleston
$248 Roundtrip, found 2 days ago
$248
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Mon, Oct 27 from Chicago to Charleston, returning Tue, Oct 28, priced at $248 found 2 days ago
Southwest Airlines
Mon, Oct 27 - Wed, Oct 29
MDW
Chicago
CHS
Charleston
$250 Roundtrip, found 5 days ago
$250
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Mon, Oct 27 from Chicago to Charleston, returning Wed, Oct 29, priced at $250 found 5 days ago
Delta
Mon, Nov 24 - Thu, Nov 27
MDW
Chicago
CHS
Charleston
$251 Roundtrip, found 3 hours ago
$251
Roundtrip
found 3 hours ago
Select Delta flight, departing Mon, Nov 24 from Chicago to Charleston, returning Thu, Nov 27, priced at $251 found 3 hours ago
Southwest Airlines
Wed, Nov 12 - Tue, Nov 18
MDW
Chicago
CHS
Charleston
$253 Roundtrip, found 3 days ago
$253
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Wed, Nov 12 from Chicago to Charleston, returning Tue, Nov 18, priced at $253 found 3 days ago
Southwest Airlines
Wed, Nov 12 - Tue, Nov 18
MDW
Chicago
CHS
Charleston
$258 Roundtrip, found 3 days ago
$258
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Wed, Nov 12 from Chicago to Charleston, returning Tue, Nov 18, priced at $258 found 3 days ago
Southwest Airlines
Fri, Oct 31 - Thu, Nov 6
MDW
Chicago
CHS
Charleston
$262 Roundtrip, found 9 hours ago
$262
Roundtrip
found 9 hours ago
Select Southwest Airlines flight, departing Fri, Oct 31 from Chicago to Charleston, returning Thu, Nov 6, priced at $262 found 9 hours ago
Southwest Airlines
Mon, Nov 17 - Wed, Nov 19
MDW
Chicago
CHS
Charleston
$263 Roundtrip, found 1 day ago
$263
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Mon, Nov 17 from Chicago to Charleston, returning Wed, Nov 19, priced at $263 found 1 day ago
Southwest Airlines
Fri, Oct 31 - Tue, Nov 4
MDW
Chicago
CHS
Charleston
$264 Roundtrip, found 3 days ago
$264
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Fri, Oct 31 from Chicago to Charleston, returning Tue, Nov 4, priced at $264 found 3 days ago
Frontier Airlines
Mon, Nov 17 - Tue, Nov 25
MDW
Chicago
CHS
Charleston
$274 Roundtrip, found 1 day ago
$274
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Mon, Nov 17 from Chicago to Charleston, returning Tue, Nov 25, priced at $274 found 1 day ago

Find the cheapest month to fly from Chicago (MDW) to Charleston (CHS)

September is typically the cheapest month to fly

From $121 - $597 per traveler.

Alternative airports near Charleston

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to Charleston Intl. CHS. Cheapest and Closest option available. Average driving time to city center is 16 minutes. Flights from $439
CHS
Charleston Intl.
CheapestClosest
Average driving time to city center16 min
Flights from $439
Flights from Chicago (MDW) to Charleston (CHS)
Origin airport
Midway Intl.
Destination airport
Charleston Intl.
Airlines serving
Delta, Frontier Airlines, Southwest Airlines
Roundtrip price
$233
Distance
745 mi
Average flight time
3 hours 1 min

Chicago to Charleston Flights

The cheapest times to fly from Chicago to Charleston

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Chicago to Charleston are during the month of October. You can find some of the cheapest flights from Chicago to Charleston with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Chicago to Charleston

Sunday is one of the best days to book for cheap flights from Chicago to Charleston: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Chicago to Charleston

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Chicago to Charleston in 2025. You can also book with separate airlines for your outbound and return journeys, from $116 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Chicago to Charleston flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Chicago to Charleston airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Frequently asked questions

How much does a flight from Midway Intl. Airport (MDW) to Charleston Intl. Airport (CHS) cost?
Grab a cheap one-way flight from $116 or cheap return flight from $233 from Midway Intl. Airport (MDW) to Charleston Intl. Airport (CHS) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight offers on this route.
What is the cheapest month to fly from Midway Intl. Airport (MDW) to Charleston Intl. Airport (CHS)?
October is the most affordable month to fly from MDW to CHS. Traveling outside of peak seasons is often the key to scoring lower fares.
Which airlines fly direct from Midway Intl. Airport (MDW) to Charleston Intl. Airport (CHS)?
Board a nonstop flight with Southwest Airlines and go straight from Midway Intl. Airport (MDW) to Charleston Intl. Airport (CHS).
What is the cheapest airline that flies from Midway Intl. Airport (MDW) to Charleston Intl. Airport (CHS)?
To find the cheapest airline that'll fly you from MDW to CHS, use Expedia's filter tool. Customize your search based on your travel style, such as preferred carriers and ideal departure window. You can then sort your results by "Price (lowest to highest)" to discover the cheapest flight right away.
How many flights per day from Midway Intl. Airport (MDW) to Charleston Intl. Airport (CHS)?
On average, Midway Intl. Airport (MDW) has 3 nonstop flights to Charleston Intl. Airport (CHS) weekly. If you want more options, take advantage of Expedia's filters to look for flights with layovers. Squeeze in a quick visit to another location or simply break up your trip.
What are the most popular departure times for flights from Midway Intl. Airport (MDW) to Charleston Intl. Airport (CHS)?
More people fly between MDW and CHS at 3 PM than at any other time of day. Rather go when it's quieter? Pick a flight outside the busiest times and you're likely to save on your ticket as well.
What day of the week has the most flights from MDW to CHS?
Friday has the most flights from Midway Intl. Airport (MDW) to Charleston Intl. Airport (CHS). Consider traveling on this day and you'll have a greater chance of finding a departure that fits your itinerary.
What is the earliest flight from Midway Intl. Airport (MDW) to Charleston Intl. Airport (CHS)?
The first flight of the day leaving from Midway Intl. Airport (MDW) is at around 3:00PM UTC-6. Board this flight and you'll reach Charleston Intl. Airport (CHS) at approximately 6:00PM UTC-5. The total time in the air is 2h.
How long does it take to fly from Midway Intl. Airport (MDW) to Charleston Intl. Airport (CHS)?
Flights from MDW to CHS have an average travel time of 2 hours. The distance between the two is 750 mi.
What is the best time to fly from Midway Intl. Airport (MDW) to Charleston Intl. Airport (CHS)?
To avoid possible delays on the Midway Intl. Airport (MDW) to Charleston Intl. Airport (CHS) route, aim to travel before 3 PM. Departures after this hour are 22% more likely to be canceled.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
What airports do you fly into for Charleston from Midway Intl. Airport (MDW)?
Charleston Intl. Airport (CHS) is the only airport in Charleston with direct flights from Midway Intl. Airport (MDW). Consider the available options and discover affordable fares on Expedia.
Is it cheaper to buy a plane ticket from Midway Intl. Airport (MDW) to Charleston Intl. Airport (CHS) last-minute?
Holding off until just before your trip to book a ticket from MDW to CHS generally means paying more. While it's possible to find some last-minute deals, they're not always guaranteed. Be flexible with your itinerary for the best chance of landing a bargain.
Is it cheaper to book a MDW to CHS flight and hotel package?
You'll generally save money by securing a MDW to CHS flight and hotel package compared to booking separately. In fact, travelers could save hundreds of dollars by bundling with Expedia. And it's simple to manage everything in one place. After selecting your ideal flights and accommodations, consider adding extras like activities, car rentals and tours.
Can I cancel or change the date of my flight from Midway Intl. Airport (MDW) to Charleston Intl. Airport (CHS)?
In most cases, you're able to cancel or reschedule your MDW to CHS flight. However, there may be additional charges, especially if your booking was made over 24 hours ago. Check your itinerary for the airline's fees and policies on flight changes, or if you'd like further details, head to our Customer Service portal.

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*Available to One Key members.