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Cheap flights from Charleston to Chicago from $119

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 8/22. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
1 adult, Economy, 0 bags

Find the cheapest flights from Charleston to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
11:30 am - 7:30 pm
CHS
-
MDW
9h 00m
2 stops
Southwest Logo
5:30 am - 3:25 pm
MDW
-
CHS
8h 55m
2 stops
$283Southwest
Thu, Sep 10 - Mon, Sep 14
Southwest Logo
8:10 am - 4:50 pm
CHS
-
MDW
9h 40m
2 stops
Southwest Logo
3:05 pm - 6:10 pm
MDW
-
CHS
2h 05mnonstop
$284Southwest
Wed, Aug 12 - Sat, Aug 15
Southwest Logo
6:30 pm - 7:40 pm
CHS
-
MDW
2h 10mnonstop
Southwest Logo
6:15 pm - 9:25 pm
MDW
-
CHS
2h 10mnonstop
$288Southwest
Thu, Aug 20 - Fri, Aug 21
Delta Logo
5:06 pm - 10:36 pm
CHS
-
MDW
6h 30m
1 stop
Delta Logo
6:05 am - 1:27 pm
MDW
-
CHS
6h 22m
1 stop
$289Delta
Wed, Sep 2 - Tue, Sep 8
Southwest Logo
8:10 am - 4:50 pm
CHS
-
MDW
9h 40m
2 stops
Southwest Logo
9:55 am - 4:40 pm
MDW
-
CHS
5h 45m
1 stop
$294Southwest
Wed, Aug 12 - Sat, Aug 15
Southwest Logo
7:35 am - 8:45 am
CHS
-
MDW
2h 10mnonstop
Southwest Logo
3:05 pm - 6:10 pm
MDW
-
CHS
2h 05mnonstop
$297Southwest
Tue, Sep 8 - Sat, Sep 12
Southwest Logo
6:30 pm - 7:40 pm
CHS
-
MDW
2h 10mnonstop
Southwest Logo
9:00 am - 3:25 pm
MDW
-
CHS
5h 25m
1 stop
$298Southwest
Thu, Aug 20 - Fri, Aug 21
Southwest Logo
8:10 am - 4:50 pm
CHS
-
MDW
9h 40m
2 stops
Southwest Logo
11:45 am - 7:20 pm
MDW
-
CHS
6h 35m
2 stops
$299Southwest
Wed, Aug 12 - Sat, Aug 15
Southwest Logo
6:30 pm - 7:40 pm
CHS
-
MDW
2h 10mnonstop
Southwest Logo
7:25 am - 4:40 pm
MDW
-
CHS
8h 15m
2 stops
$303Southwest
Thu, Aug 20 - Fri, Aug 21
Delta Logo
6:45 pm - 10:36 pm
CHS
-
MDW
4h 51m
1 stop
Delta Logo
12:46 pm - 6:52 pm
MDW
-
CHS
5h 06m
1 stop
$308Delta
Wed, Aug 12 - Mon, Aug 17

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Southwest flights from Charleston to Chicago Midway Airport

Our best Southwest deals on Charleston to Chicago Midway Airport flight tickets
Southwest
Sep 10
CHS11:30 amCharleston
9h 00m
2 stops
MDW7:30 pmChicago Midway
Sep 14
MDW5:30 amChicago Midway
8h 55m
2 stops
CHS3:25 pmCharleston
$283
Southwest
Aug 12
CHS8:10 amCharleston
9h 40m
2 stops
MDW4:50 pmChicago Midway
Aug 15
MDW3:05 pmChicago Midway
2h 05m
CHS6:10 pmCharleston
$284
Southwest
Aug 20
CHS6:30 pmCharleston
2h 10m
MDW7:40 pmChicago Midway
Aug 21
MDW6:15 pmChicago Midway
2h 10m
CHS9:25 pmCharleston
$288

Delta flights from Charleston to Chicago Midway Airport

Our best Delta deals on Charleston to Chicago Midway Airport flight tickets
Delta
Sep 2
CHS5:06 pmCharleston
6h 30m
1 stop
MDW10:36 pmChicago Midway
Sep 8
MDW6:05 amChicago Midway
6h 22m
1 stop
CHS1:27 pmCharleston
$289
Delta
Aug 12
CHS6:45 pmCharleston
4h 51m
1 stop
MDW10:36 pmChicago Midway
Aug 17
MDW12:46 pmChicago Midway
5h 06m
1 stop
CHS6:52 pmCharleston
$308
Delta
Aug 20
CHS12:59 pmCharleston
6h 34m
1 stop
MDW6:33 pmChicago Midway
Sep 1
MDW4:39 pmChicago Midway
4h 03m
1 stop
CHS9:42 pmCharleston
$318

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 July 25, 2026.
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

Cheapest round-trip

CharlestonChicago

CHS - MDW

CHSMDW

Charleston

Thu 9/10

11:30 am-7:30 pm

2 stops9h 00m

Chicago Midway

Mon 9/14

5:30 am-3:25 pm

2 stops8h 55m

$283

CharlestonChicago

CHS - MDW

CHSMDW

Charleston

Wed 8/12

8:10 am-4:50 pm

2 stops9h 40m

Chicago Midway

Sat 8/15

3:05 pm-6:10 pm

Nonstop2h 05m

$284

CharlestonChicago

CHS - MDW

CHSMDW

Charleston

Thu 8/20

6:30 pm-7:40 pm

Nonstop2h 10m

Chicago Midway

Fri 8/21

6:15 pm-9:25 pm

Nonstop2h 10m

$288

CharlestonChicago

CHS - MDW

CHSMDW

Charleston

Wed 9/2

5:06 pm-10:36 pm

1 stop6h 30m

Chicago Midway

Tue 9/8

6:05 am-1:27 pm

1 stop6h 22m

$289

CharlestonChicago

CHS - MDW

CHSMDW

Charleston

Wed 8/12

8:10 am-4:50 pm

2 stops9h 40m

Chicago Midway

Sat 8/15

9:55 am-4:40 pm

1 stop5h 45m

$294
Quickest round-trip

CharlestonChicago

CHS - MDW

CHSMDW

Charleston

Tue 9/8

7:35 am-8:45 am

Nonstop2h 10m

Chicago Midway

Sat 9/12

3:05 pm-6:10 pm

Nonstop2h 05m

$297

CharlestonChicago

CHS - MDW

CHSMDW

Charleston

Thu 8/20

6:30 pm-7:40 pm

Nonstop2h 10m

Chicago Midway

Fri 8/21

9:00 am-3:25 pm

1 stop5h 25m

$298

CharlestonChicago

CHS - MDW

CHSMDW

Charleston

Wed 8/12

8:10 am-4:50 pm

2 stops9h 40m

Chicago Midway

Sat 8/15

11:45 am-7:20 pm

2 stops6h 35m

$299

CharlestonChicago

CHS - MDW

CHSMDW

Charleston

Thu 8/20

6:30 pm-7:40 pm

Nonstop2h 10m

Chicago Midway

Fri 8/21

7:25 am-4:40 pm

2 stops8h 15m

$303

CharlestonChicago

CHS - MDW

CHSMDW

Charleston

Wed 8/12

6:45 pm-10:36 pm

1 stop4h 51m

Chicago Midway

Mon 8/17

12:46 pm-6:52 pm

1 stop5h 06m

$308

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 typical price of a round-trip flight between Charleston and Chicago Midway Airport?

Prices are currently low for flights on this route.

Typical prices usually range from $292 to $396.
The lowest price recently found on this route was $283.

What is the cheapest month to fly to Chicago Midway Airport?

The month of March is, on average, the cheapest month to fly to Chicago Midway Airport from Charleston, with most prices found around $0. If you are unable to visit Chicago Midway Airport during the month of March, then departing from Charleston during the month October is also very affordable. Most momondo users find prices during this month for around $190.

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 $396. 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 $477.

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 $384 when looking at flights departing in the afternoon. Try not to purchase tickets in the evening because they tend to be around $449. 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 Airport flights?

There is only 1 cabin class available to choose from on Charleston to Chicago Midway Airport 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?

No. A direct flight is the cheapest option for a flight between Charleston to Chicago Midway Airport.

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

$222

Fastest flight time

2h 10m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from Charleston in the past 72 hours is $222. The best round-trip flight deal from Charleston to Chicago Midway Airport found on momondo in the last 72 hours is $389.
The fastest flight from Charleston to Chicago Midway Airport takes 2h 10m
Direct flights go from Charleston to Chicago Midway Airport every day.
Search flight deals

Frequently asked questions about flying from Charleston to Chicago Midway Airport

  • How far is Charleston to Chicago Midway by plane?

    There are 755.1 mi between Charleston and Chicago Midway. 2h 10m 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
8.0
4,233 reviews
Search Southwest 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 8 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 $308. Our users have rated Southwest at 8.0/10.

Traveling to a place near Chicago?

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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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