$91 Cheap Flights from Chicago (MDW) to Charleston (CHS)

View $91 flight on Thu, Sep 25, 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 $91 for one-way flights and $181 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Southwest Airlines
Thu, Aug 7 - Mon, Aug 11
MDW
Chicago
CHS
Charleston
$181 Roundtrip, found 3 hours ago
$181
Roundtrip
found 3 hours ago
Select Southwest Airlines flight, departing Thu, Aug 7 from Chicago to Charleston, returning Mon, Aug 11, priced at $181 found 3 hours ago
Southwest Airlines
Sat, Oct 11 - Wed, Oct 15
MDW
Chicago
CHS
Charleston
$187 Roundtrip, found 2 days ago
$187
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Sat, Oct 11 from Chicago to Charleston, returning Wed, Oct 15, priced at $187 found 2 days ago
Southwest Airlines
Wed, Oct 15 - Sat, Oct 18
MDW
Chicago
CHS
Charleston
$190 Roundtrip, found 1 day ago
$190
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Wed, Oct 15 from Chicago to Charleston, returning Sat, Oct 18, priced at $190 found 1 day ago
Southwest Airlines
Thu, Sep 25 - Mon, Sep 29
MDW
Chicago
CHS
Charleston
$191 Roundtrip, found 3 hours ago
$191
Roundtrip
found 3 hours ago
Select Southwest Airlines flight, departing Thu, Sep 25 from Chicago to Charleston, returning Mon, Sep 29, priced at $191 found 3 hours ago
Delta
Thu, Aug 7 - Mon, Aug 11
MDW
Chicago
CHS
Charleston
$192 Roundtrip, found 3 hours ago
$192
Roundtrip
found 3 hours ago
Select Delta flight, departing Thu, Aug 7 from Chicago to Charleston, returning Mon, Aug 11, priced at $192 found 3 hours ago
Southwest Airlines
Fri, Sep 12 - Mon, Sep 15
MDW
Chicago
CHS
Charleston
$193 Roundtrip, found 3 hours ago
$193
Roundtrip
found 3 hours ago
Select Southwest Airlines flight, departing Fri, Sep 12 from Chicago to Charleston, returning Mon, Sep 15, priced at $193 found 3 hours ago
Southwest Airlines
Thu, Aug 7 - Mon, Aug 11
MDW
Chicago
CHS
Charleston
$196 Roundtrip, found 3 hours ago
$196
Roundtrip
found 3 hours ago
Select Southwest Airlines flight, departing Thu, Aug 7 from Chicago to Charleston, returning Mon, Aug 11, priced at $196 found 3 hours ago
Southwest Airlines
Thu, Oct 2 - Mon, Oct 6
MDW
Chicago
CHS
Charleston
$197 Roundtrip, found 5 days ago
$197
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Thu, Oct 2 from Chicago to Charleston, returning Mon, Oct 6, priced at $197 found 5 days ago
Southwest Airlines
Thu, Sep 18 - Mon, Sep 22
MDW
Chicago
CHS
Charleston
$199 Roundtrip, found 1 day ago
$199
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Thu, Sep 18 from Chicago to Charleston, returning Mon, Sep 22, priced at $199 found 1 day ago
Frontier Airlines
Mon, Oct 20 - Sat, Oct 25
MDW
Chicago
CHS
Charleston
$227 Roundtrip, found 3 days ago
$227
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Mon, Oct 20 from Chicago to Charleston, returning Sat, Oct 25, priced at $227 found 3 days ago

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

September is typically the cheapest month to fly

From $175 - $576 per traveler.

Graph displaying average flight prices per month

Flights from Chicago (MDW) to Charleston (CHS)
Origin airport
Midway Intl.
Destination airport
Charleston Intl.
Airlines serving
Delta, Frontier Airlines, Southwest Airlines
Roundtrip price
$181
Distance
745 mi
Average flight time
3 hours 5 mins

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 August. 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 $91 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 cheap return tickets starting from $181 from Midway Intl. Airport (MDW) to Charleston Intl. Airport (CHS). This information is based on the cheapest price found on Expedia for this return journey departing within the next three months. This airfare is for a Southwest Airlines flight leaving MDW on July 26 2025 and touching down at CHS. The price was last updated on July 1 2025 and has not changed since.
What is the cheapest month to fly from MDW to CHS?
Fly straight from MDW to CHS in September to land cheaper fares. You can find a one-way Southwest Airlines flight for $91 leaving on September 23 2025. This price is based on the cheapest direct flight found on Expedia for this route in the next 330 days. The price was last updated on July 1 2025 and remains unchanged.
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 MDW to CHS?
Fly from MDW to CHS with Southwest Airlines. This carrier currently has the cheapest one-way ticket on this route, starting at $91. This fare is based on the lowest price found on Expedia departing within the next three months. The flight takes off from MDW on September 23 2025. Prices were last updated on July 1 2025 and have not changed since.
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.