$127 Cheap Flights from Charleston (CHS) to Chicago (MDW)

View $127 flight on Wed, May 28, 2025Opens in a new window

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Cheap Flights from Charleston to Chicago (CHS-MDW)

Prices were available within the past 7 days and start at $127 for one-way flights and $263 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Southwest Airlines
Tue, May 20 - Wed, May 28
CHS
Charleston
MDW
Chicago
$263 Roundtrip, found 3 days ago
$263
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Tue, May 20 from Charleston to Chicago, returning Wed, May 28, priced at $263 found 3 days ago
Southwest Airlines
Wed, May 28 - Tue, Jun 3
CHS
Charleston
MDW
Chicago
$266 Roundtrip, found 3 hours ago
$266
Roundtrip
found 3 hours ago
Select Southwest Airlines flight, departing Wed, May 28 from Charleston to Chicago, returning Tue, Jun 3, priced at $266 found 3 hours ago
Southwest Airlines
Wed, May 28 - Thu, Jun 5
CHS
Charleston
MDW
Chicago
$269 Roundtrip, just found
$269
Roundtrip
just found
Select Southwest Airlines flight, departing Wed, May 28 from Charleston to Chicago, returning Thu, Jun 5, priced at $269 just found
Southwest Airlines
Tue, May 20 - Wed, May 28
CHS
Charleston
MDW
Chicago
$273 Roundtrip, found 3 days ago
$273
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Tue, May 20 from Charleston to Chicago, returning Wed, May 28, priced at $273 found 3 days ago
Delta
Tue, May 20 - Wed, May 28
CHS
Charleston
MDW
Chicago
$273 Roundtrip, found 1 day ago
$273
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, May 20 from Charleston to Chicago, returning Wed, May 28, priced at $273 found 1 day ago
Southwest Airlines
Wed, May 28 - Tue, Jun 3
CHS
Charleston
MDW
Chicago
$276 Roundtrip, found 3 hours ago
$276
Roundtrip
found 3 hours ago
Select Southwest Airlines flight, departing Wed, May 28 from Charleston to Chicago, returning Tue, Jun 3, priced at $276 found 3 hours ago
Southwest Airlines
Wed, May 28 - Tue, Jun 3
CHS
Charleston
MDW
Chicago
$278 Roundtrip, found 3 hours ago
$278
Roundtrip
found 3 hours ago
Select Southwest Airlines flight, departing Wed, May 28 from Charleston to Chicago, returning Tue, Jun 3, priced at $278 found 3 hours ago
Southwest Airlines
Wed, May 28 - Thu, Jun 5
CHS
Charleston
MDW
Chicago
$279 Roundtrip, just found
$279
Roundtrip
just found
Select Southwest Airlines flight, departing Wed, May 28 from Charleston to Chicago, returning Thu, Jun 5, priced at $279 just found
Southwest Airlines
Wed, May 28 - Tue, Jun 3
CHS
Charleston
MDW
Chicago
$281 Roundtrip, found 3 hours ago
$281
Roundtrip
found 3 hours ago
Select Southwest Airlines flight, departing Wed, May 28 from Charleston to Chicago, returning Tue, Jun 3, priced at $281 found 3 hours ago
Southwest Airlines
Wed, Jun 18 - Thu, Jun 19
CHS
Charleston
MDW
Chicago
$282 Roundtrip, found 2 hours ago
$282
Roundtrip
found 2 hours ago
Select Southwest Airlines flight, departing Wed, Jun 18 from Charleston to Chicago, returning Thu, Jun 19, priced at $282 found 2 hours ago
Flights from Charleston (CHS) to Chicago (MDW)
Origin airport
Charleston Intl.
Destination airport
Midway Intl.
Airlines serving
Delta, Southwest Airlines
Roundtrip price
$263
Distance
745 mi

Charleston to Chicago Flights

The cheapest times to fly from Charleston to Chicago

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 Charleston to Chicago are during the month of May. You can find some of the cheapest flights from Charleston to Chicago with Expedia's search tool and vast selection of airlines.

The best time to book a flight from Charleston to Chicago

Sunday is one of the best days to book for cheap flights from Charleston to Chicago: 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 Charleston to Chicago

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 Charleston to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from $127 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 Charleston to Chicago 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 Charleston to Chicago 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 Charleston Intl. Airport (CHS) to Midway Intl. Airport (MDW) cost?
Pick up cheap return tickets starting at $253 from Charleston Intl. Airport (CHS) to Midway Intl. Airport (MDW). 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 and American Airlines flight leaving CHS on May 20 2025 and touching down at MDW. The price was last updated on April 23 2025 and has not changed since.
What is the cheapest month to fly from CHS to MDW?
The cheapest flights from CHS to MDW are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
Which airlines fly direct from Charleston Intl. Airport (CHS) to Midway Intl. Airport (MDW)?
Hop on a direct flight with Southwest Airlines and travel straight from Charleston Intl. Airport (CHS) to Midway Intl. Airport (MDW).
What is the cheapest airline that flies from CHS to MDW?
Book a flight from CHS to MDW with Southwest Airlines. This carrier currently offers the cheapest one-way ticket for this route, starting from $127. This fare is based on the lowest price found on Expedia departing within the next three months. The flight takes off from CHS on June 3 2025. Prices were last updated on April 23 2025 and have not changed since.
How many flights per day from Charleston Intl. Airport (CHS) to Midway Intl. Airport (MDW)?
On average, you can take your pick of 3 nonstop flights taking off from Charleston Intl. Airport (CHS) to Midway Intl. Airport (MDW) per week. If you can’t see one that fits your schedule, consider catching a flight that has a layover. Filter your search on Expedia to include one or two stops and select the best alternative.
What are the most popular departure times for flights from Charleston Intl. Airport (CHS) to Midway Intl. Airport (MDW)?
More passengers fly between CHS and MDW at 8 AM than at any other time. Looking to skip the crowds? Try choosing a quieter departure window and it’s possible you’ll save on your fare as well.
What day of the week has the most flights from CHS to MDW?
Friday has the most flights from Charleston Intl. Airport (CHS) to Midway Intl. Airport (MDW). 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 Charleston Intl. Airport (CHS) to Midway Intl. Airport (MDW)?
Charleston Intl. Airport (CHS)’s first flight to Midway Intl. Airport (MDW) departs at approximately 8:10AM UTC-5. With a total journey time of 2h 20m, you’ll touch down at around 9:30AM UTC-6.
How long does it take to fly from Charleston Intl. Airport (CHS) to Midway Intl. Airport (MDW)?
Flights from CHS to MDW have an average travel time of 2 hours and 20 minutes. The distance between the two is 750 mi.
What is the best time to fly from Charleston Intl. Airport (CHS) to Midway Intl. Airport (MDW)?
To avoid potential delays on the Charleston Intl. Airport (CHS) to Midway Intl. Airport (MDW) route, aim to travel before 3 PM. Departures after this time have a 22% higher chance of being 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 Chicago from Charleston Intl. Airport (CHS)?
Hop on a direct flight from Charleston Intl. Airport (CHS) to Chicago and land at O’Hare Intl. Airport (ORD). An alternative point of entry into the city is Midway Intl. Airport (MDW).
Is it cheaper to buy a plane ticket from Charleston Intl. Airport (CHS) to Midway Intl. Airport (MDW) last-minute?
Holding off until just before your departure to book your flight from CHS to MDW often results in higher prices. While you may find some last-minute offers, they’re not always guaranteed. Keep your travel plans flexible for the best chance of snagging a bargain.
Is it cheaper to book a CHS to MDW flight and hotel package?
Compared with arranging flights and hotels separately, booking a CHS to MDW flight and hotel package with Expedia could lead to significant savings. What’s more, having it all in one place will take the hassle out of planning your trip. Simply secure your flights and select from our wide range of hotels, then customize your trip with extras like tours, activities and car rentals.
Can I cancel or change the date of my flight from Charleston Intl. Airport (CHS) to Midway Intl. Airport (MDW)?
In most cases, you can cancel or reschedule your CHS to MDW flight. However, there may be additional charges, especially if your booking was made more than 24 hours ago. Double-check your itinerary for the airline’s fees and rules 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.