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Cheap flights from Charleston to Chicago from $68

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Charleston to Chicago departing on 1/15. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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0 bags

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Find the cheapest flights from Charleston to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
11:40 am - 6:35 pm
CHS
-
MDW
7h 55m2 stops
Southwest Logo
3:10 pm - 6:10 pm
MDW
-
CHS
2h 00mnonstop
$289Southwest
Tue, Feb 10 - Sat, Feb 14
Delta Logo
12:53 pm - 4:29 pm
CHS
-
MDW
4h 36m1 stop
Delta Logo
5:31 pm - 11:55 pm
MDW
-
CHS
5h 24m1 stop
$294Delta
Wed, Jan 14 - Sat, Jan 17
Southwest Logo
6:55 am - 2:20 pm
CHS
-
MDW
8h 25m2 stops
Southwest Logo
2:10 pm - 8:55 pm
MDW
-
CHS
5h 45m1 stop
$299Southwest
Tue, Feb 10 - Sat, Feb 14
Southwest Logo
2:00 pm - 5:20 pm
CHS
-
MDW
4h 20m1 stop
Southwest Logo
2:55 pm - 6:00 pm
MDW
-
CHS
2h 05mnonstop
$302Southwest
Sat, Jan 17 - Mon, Jan 19
Southwest Logo
6:55 am - 2:20 pm
CHS
-
MDW
8h 25m2 stops
Southwest Logo
2:10 pm - 8:55 pm
MDW
-
CHS
5h 45m2 stops
$304Southwest
Tue, Feb 10 - Sat, Feb 14
Southwest Logo
11:05 am - 6:40 pm
CHS
-
MDW
8h 35m2 stops
Southwest Logo
2:55 pm - 6:00 pm
MDW
-
CHS
2h 05mnonstop
$307Southwest
Sat, Jan 17 - Mon, Jan 19
Delta Logo
5:30 pm - 10:22 pm
CHS
-
MDW
5h 52m1 stop
Delta Logo
6:14 pm - 11:55 pm
MDW
-
CHS
4h 41m1 stop
$312Delta
Tue, Jan 20 - Thu, Jan 22
Southwest Logo
11:05 am - 4:55 pm
CHS
-
MDW
6h 50m1 stop
Southwest Logo
12:30 pm - 9:40 pm
MDW
-
CHS
8h 10m2 stops
$317Southwest
Sat, Jan 17 - Mon, Jan 19
Delta Logo
5:43 pm - 10:22 pm
CHS
-
MDW
5h 39m1 stop
Delta Logo
6:25 am - 2:06 pm
MDW
-
CHS
6h 41m1 stop
$319Delta
Sat, Jan 24 - Sat, Jan 31
Southwest Logo
11:05 am - 6:40 pm
CHS
-
MDW
8h 35m2 stops
Southwest Logo
12:30 pm - 9:40 pm
MDW
-
CHS
8h 10m2 stops
$322Southwest
Sat, Jan 17 - Mon, Jan 19

Southwest flights from Charleston to Chicago Midway Airport

Our best Southwest deals on Charleston to Chicago Midway Airport flight tickets
Southwest
Feb 10
CHS11:40 amCharleston
7h 55m
2 stops
MDW6:35 pmChicago Midway
Feb 14
MDW3:10 pmChicago Midway
2h 00m
CHS6:10 pmCharleston
$289
Find similar
Southwest
Feb 10
CHS6:55 amCharleston
8h 25m
2 stops
MDW2:20 pmChicago Midway
Feb 14
MDW2:10 pmChicago Midway
5h 45m
1 stop
CHS8:55 pmCharleston
$299
Find similar
Southwest
Jan 17
CHS2:00 pmCharleston
4h 20m
1 stop
MDW5:20 pmChicago Midway
Jan 19
MDW2:55 pmChicago Midway
2h 05m
CHS6:00 pmCharleston
$302
Find similar

Delta flights from Charleston to Chicago Midway Airport

Our best Delta deals on Charleston to Chicago Midway Airport flight tickets
Delta
Jan 14
CHS12:53 pmCharleston
4h 36m
1 stop
MDW4:29 pmChicago Midway
Jan 17
MDW5:31 pmChicago Midway
5h 24m
1 stop
CHS11:55 pmCharleston
$294
Find similar
Delta
Jan 20
CHS5:30 pmCharleston
5h 52m
1 stop
MDW10:22 pmChicago Midway
Jan 22
MDW6:14 pmChicago Midway
4h 41m
1 stop
CHS11:55 pmCharleston
$312
Find similar
Delta
Jan 24
CHS5:43 pmCharleston
5h 39m
1 stop
MDW10:22 pmChicago Midway
Jan 31
MDW6:25 amChicago Midway
6h 41m
1 stop
CHS2:06 pmCharleston
$319
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Charleston to Chicago Midway Airport 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, momondo users made 832,500 searches. Data last updated December 11, 2025.
Use the filters below to find and compare flights from Charleston to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

CharlestonChicago

CHS - MDW

CHSMDW

Charleston

Tue 2/10

11:40 am-6:35 pm

2 stops7h 55m

Chicago Midway

Sat 2/14

3:10 pm-6:10 pm

Nonstop2h 00m

$289

CharlestonChicago

CHS - MDW

CHSMDW

Charleston

Wed 1/14

12:53 pm-4:29 pm

1 stop4h 36m

Chicago Midway

Sat 1/17

5:31 pm-11:55 pm

1 stop5h 24m

$294

CharlestonChicago

CHS - MDW

CHSMDW

Charleston

Tue 2/10

6:55 am-2:20 pm

2 stops8h 25m

Chicago Midway

Sat 2/14

2:10 pm-8:55 pm

1 stop5h 45m

$299

CharlestonChicago

CHS - MDW

CHSMDW

Charleston

Sat 1/17

2:00 pm-5:20 pm

1 stop4h 20m

Chicago Midway

Mon 1/19

2:55 pm-6:00 pm

Nonstop2h 05m

$302

CharlestonChicago

CHS - MDW

CHSMDW

Charleston

Tue 2/10

6:55 am-2:20 pm

2 stops8h 25m

Chicago Midway

Sat 2/14

2:10 pm-8:55 pm

2 stops5h 45m

$304

CharlestonChicago

CHS - MDW

CHSMDW

Charleston

Sat 1/17

11:05 am-6:40 pm

2 stops8h 35m

Chicago Midway

Mon 1/19

2:55 pm-6:00 pm

Nonstop2h 05m

$307

CharlestonChicago

CHS - MDW

CHSMDW

Charleston

Tue 1/20

5:30 pm-10:22 pm

1 stop5h 52m

Chicago Midway

Thu 1/22

6:14 pm-11:55 pm

1 stop4h 41m

$312

CharlestonChicago

CHS - MDW

CHSMDW

Charleston

Sat 1/17

11:05 am-4:55 pm

1 stop6h 50m

Chicago Midway

Mon 1/19

12:30 pm-9:40 pm

2 stops8h 10m

$317

CharlestonChicago

CHS - MDW

CHSMDW

Charleston

Sat 1/24

5:43 pm-10:22 pm

1 stop5h 39m

Chicago Midway

Sat 1/31

6:25 am-2:06 pm

1 stop6h 41m

$319

CharlestonChicago

CHS - MDW

CHSMDW

Charleston

Sat 1/17

11:05 am-6:40 pm

2 stops8h 35m

Chicago Midway

Mon 1/19

12:30 pm-9:40 pm

2 stops8h 10m

$322

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Chicago from

How to get the cheapest flight ticket from Charleston to Chicago Midway Airport

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest day to depart on your flight to Chicago Midway Airport?

According to our data, Wednesday is the cheapest day to fly to Chicago Midway Airport from Charleston. The lowest ticket price found for a Wednesday departure recently was $316. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Sunday is the most expensive day to depart from Charleston because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $496.

What is the cheapest time of day to depart on your flight to Chicago Midway Airport?

Flying to Chicago Midway Airport from Charleston in the afternoon is the least expensive time of day to depart. momondo users have found prices as low as $304 when looking at flights departing in the afternoon. Try not to purchase tickets in the evening because they tend to be around $423. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest Charleston to Chicago Midway flight route?

Fly from Charleston to Chicago Midway for the best Charleston - Chicago Midway flight prices

What cabin class options are available on Charleston to Chicago Midway flights?

There is only 1 cabin class available to choose from on Charleston to Chicago Midway flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Charleston to Chicago Midway Airport flights?

You could potentially save up to 39% on your flight if you consider stops on a Charleston to Chicago Midway Airport flight.

When to book flights from Charleston to Chicago Midway Airport

Are you open to changing your travel dates? Check out the ideal times to fly from Charleston to Chicago Midway Airport according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Charleston to Chicago Midway Airport (CHS to MDW) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Charleston to Chicago Midway Airport

Best Price Found

$194

Fastest flight time

2h 15m

Direct flights

Mon, Tue, Thu, Fri, Sat and Sun
The best one-way flight to Chicago Midway Airport from Charleston in the past 72 hours is $194. The best round-trip flight deal from Charleston to Chicago Midway Airport found on momondo in the last 72 hours is $422.
The fastest flight from Charleston to Chicago Midway Airport takes 2h 15m
Direct flights go from Charleston to Chicago Midway Airport on Monday, Tuesday, Thursday, Friday, Saturday and Sunday. There are no airlines offering direct flights.
Search flight deals

  • How far is Charleston to Chicago Midway by plane?

    There are 755.1 mi between Charleston and Chicago Midway. 2h 15m is a normal flight duration for this route.

  • When did momondo last update prices for flights from Charleston Airport to Chicago Midway Airport?

    Prices for flights from Charleston Airport to Chicago Midway Airport are updated daily.

  • How many operators does momondo search for flights from Charleston Airport to Chicago Midway Airport?

  • How old do you have to be to fly from Charleston Airport to Chicago Midway Airport?

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Charleston Airport to Chicago Midway Airport.

  • What documentation or ID do you need to fly to Chicago Midway Airport?

    The required travel and health documents for your Chicago Midway Airport trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago Midway Airport. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

  • What is the most popular plane model from Charleston to Chicago Midway Airport?

  • What is the most popular airline from Charleston to Chicago Midway Airport?

Best airlines flying from Charleston to Chicago Midway Airport

Compare and see reviews for airlines that fly from Charleston to Chicago Midway Airport with momondo
Airline
Rating
Free Cancellation
Price
SouthwestPriceFrom $190Free CancellationRating
7.9
4,253 reviews
Search Southwest flights
DeltaPriceFrom $368Free CancellationRating
7.9
8,008 reviews
Search Delta flights

  • Southwest Flights From Charleston to Chicago Midway Airport

    Southwest is one of the most popular airlines flying from Charleston to Chicago Midway Airport, operating 4 flights/week on average for this route. A good Southwest flight deal for Charleston to Chicago Midway Airport starts from $190 round-trip, up to an average price of $363. Our users have rated Southwest at 7.9/10.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
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Saint John

Why use momondo?

Why should I use momondo to find a flight deal from Charleston to Chicago?

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Charleston to Chicago for you.

Can I find flights from Charleston to Chicago with flexible booking policies on momondo?

momondo does allow users to show only those flights to Chicago from Charleston which offer a flexible booking policy as well as other useful filters and features.

How can momondo help me find flights from Charleston to Chicago?

Once all potential Charleston to Chicago flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

I’m not ready to book a flight from Charleston to Chicago right now. Can momondo alert me if prices change?

Yes. momondo can track prices for Charleston to Chicago flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.

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