$131 Cheap Flights from Charleston (CHS) to Chicago (MDW)

View $131 flight on Thu, Feb 19, 2026Opens in a new window

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

Cheap Flights from Charleston to Chicago (CHS-MDW)

Prices were available within the past 7 days and start at $131 for one-way flights and $173 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frontier Airlines
Sun, Nov 9 - Mon, Nov 17
CHS
Charleston
MDW
Chicago
$173 Roundtrip, found 3 days ago
$173
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Sun, Nov 9 from Charleston to Chicago, returning Mon, Nov 17, priced at $173 found 3 days ago
Frontier Airlines
Sun, Nov 9 - Mon, Nov 17
CHS
Charleston
MDW
Chicago
$179 Roundtrip, found 5 days ago
$179
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Sun, Nov 9 from Charleston to Chicago, returning Mon, Nov 17, priced at $179 found 5 days ago
Frontier Airlines
Sun, Nov 9 - Sun, Nov 16
CHS
Charleston
MDW
Chicago
$206 Roundtrip, found 3 days ago
$206
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Sun, Nov 9 from Charleston to Chicago, returning Sun, Nov 16, priced at $206 found 3 days ago
Frontier Airlines
Sun, Nov 9 - Fri, Nov 14
CHS
Charleston
MDW
Chicago
$212 Roundtrip, found 4 days ago
$212
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Sun, Nov 9 from Charleston to Chicago, returning Fri, Nov 14, priced at $212 found 4 days ago
Frontier Airlines
Sun, Nov 9 - Sat, Nov 22
CHS
Charleston
MDW
Chicago
$253 Roundtrip, found 3 days ago
$253
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Sun, Nov 9 from Charleston to Chicago, returning Sat, Nov 22, priced at $253 found 3 days ago
Frontier Airlines
Sun, Nov 9 - Sat, Nov 22
CHS
Charleston
MDW
Chicago
$259 Roundtrip, found 5 days ago
$259
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Sun, Nov 9 from Charleston to Chicago, returning Sat, Nov 22, priced at $259 found 5 days ago
Southwest Airlines
Thu, Feb 12 - Sat, Feb 14
CHS
Charleston
MDW
Chicago
$260 Roundtrip, found 5 days ago
$260
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Thu, Feb 12 from Charleston to Chicago, returning Sat, Feb 14, priced at $260 found 5 days ago
Southwest Airlines
Thu, Feb 12 - Sat, Feb 14
CHS
Charleston
MDW
Chicago
$266 Roundtrip, found 5 days ago
$266
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Thu, Feb 12 from Charleston to Chicago, returning Sat, Feb 14, priced at $266 found 5 days ago
Southwest Airlines
Wed, Dec 31 - Thu, Jan 1
CHS
Charleston
MDW
Chicago
$266 Roundtrip, found 6 days ago
$266
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Wed, Dec 31 from Charleston to Chicago, returning Thu, Jan 1, priced at $266 found 6 days ago
Delta
Mon, Nov 24 - Thu, Nov 27
CHS
Charleston
MDW
Chicago
$299 Roundtrip, just found
$299
Roundtrip
just found
Select Delta flight, departing Mon, Nov 24 from Charleston to Chicago, returning Thu, Nov 27, priced at $299 just found

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

August is typically the cheapest month to fly

From $135 - $524 per traveler.

Alternative airports near Chicago

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

Select flight to O'Hare Intl. ORD. Cheapest option available. Average driving time to city center is 23 minutes. Flights from $172
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from $172

Frequently asked questions

How much does a flight from Charleston Intl. Airport (CHS) to Midway Intl. Airport (MDW) cost?
Snag a cheap one-way flight from $131 or cheap return flight from $173 from Charleston Intl. Airport (CHS) to Midway Intl. Airport (MDW) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to see our cheapest flight deals on this route.
What is the cheapest month to fly from Charleston Intl. Airport (CHS) to Midway Intl. Airport (MDW)?
Flying in November is a great way to save, as it's the cheapest month for flights between CHS and MDW. You'll usually find the lowest prices during the off-season.
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 Charleston Intl. Airport (CHS) to Midway Intl. Airport (MDW)?
To find the cheapest airline flying from CHS to MDW, use Expedia's filter tool. Customize your search based on your travel needs, such as preferred carriers and ideal departure window. You can then sort your results by "Price (lowest to highest)" to list the most affordable options first.
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.

Travel information

Origin airport
Charleston Intl.
Destination airport
Midway Intl.
Airlines serving
Delta, Frontier Airlines, Southwest Airlines
Roundtrip price
$173
Distance
745 mi
Average flight time
3 hours 6 mins

Book with confidence

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 November. 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 $131 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.

 

Charleston to Chicago Flights

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*Available to One Key members.