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Cheap flights from Charleston to Chicago from $65

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 4/21. 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
0 bags

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Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
3:26 pm - 1:00 pm
CHS
-
MDW
22h 34m
1 stop
Multiple Airlines Logo
7:30 am - 2:31 pm
MDW
-
CHS
6h 01m
1 stop
$135Multiple Airlines
Tue, May 5 - Sat, May 9
Multiple Airlines Logo
9:35 am - 1:00 pm
CHS
-
MDW
28h 25m
1 stop
Multiple Airlines Logo
7:30 am - 2:31 pm
MDW
-
CHS
6h 01m
1 stop
$160Multiple Airlines
Mon, Apr 27 - Wed, Apr 29
Multiple Airlines Logo
5:00 pm - 12:02 pm
CHS
-
MDW
20h 02m
1 stop
Multiple Airlines Logo
9:51 pm - 8:38 am
MDW
-
CHS
9h 47m
1 stop
$169Multiple Airlines
Sat, Mar 7 - Mon, Mar 9
Multiple Airlines Logo
5:00 pm - 12:02 pm
CHS
-
MDW
20h 02m
1 stop
Multiple Airlines Logo
9:51 pm - 8:38 am
MDW
-
CHS
9h 47m
1 stop
$172Multiple Airlines
Sat, Mar 7 - Mon, Mar 9
Multiple Airlines Logo
3:26 pm - 1:00 pm
CHS
-
MDW
22h 34m
1 stop
Multiple Airlines Logo
7:30 am - 2:31 pm
MDW
-
CHS
6h 01m
1 stop
$173Multiple Airlines
Tue, May 5 - Sat, May 9
Multiple Airlines Logo
3:26 pm - 1:00 pm
CHS
-
MDW
22h 34m
1 stop
Multiple Airlines Logo
7:30 am - 2:31 pm
MDW
-
CHS
6h 01m
1 stop
$180Multiple Airlines
Tue, May 5 - Sat, May 9
Multiple Airlines Logo
3:21 pm - 4:13 pm
CHS
-
MDW
25h 52m
1 stop
Multiple Airlines Logo
7:30 am - 2:31 pm
MDW
-
CHS
6h 01m
1 stop
$181Multiple Airlines
Fri, Apr 24 - Mon, Apr 27
Multiple Airlines Logo
5:00 pm - 12:02 pm
CHS
-
MDW
20h 02m
1 stop
Multiple Airlines Logo
9:51 pm - 4:05 pm
MDW
-
CHS
17h 14m
2 stops
$187Multiple Airlines
Sat, Mar 7 - Mon, Mar 9
Multiple Airlines Logo
3:26 pm - 1:00 pm
CHS
-
MDW
22h 34m
1 stop
Multiple Airlines Logo
7:30 am - 2:31 pm
MDW
-
CHS
6h 01m
1 stop
$200Multiple Airlines
Wed, May 6 - Fri, May 8
Multiple Airlines Logo
12:04 pm - 1:02 pm
CHS
-
MDW
25h 58m
1 stop
Multiple Airlines Logo
9:51 pm - 8:38 am
MDW
-
CHS
9h 47m
1 stop
$210Multiple Airlines
Mon, Mar 16 - Mon, Mar 23

Southwest flights from Charleston to Chicago Midway Airport

Our best Southwest deals on Charleston to Chicago Midway Airport flight tickets
Southwest
May 5
CHS7:15 amCharleston
2h 15m
MDW8:30 amChicago Midway
May 9
MDW12:45 pmChicago Midway
6h 30m
1 stop
CHS8:15 pmCharleston
$290
Southwest
Mar 17
CHS4:35 pmCharleston
2h 20m
MDW5:55 pmChicago Midway
Mar 18
MDW3:35 pmChicago Midway
4h 35m
1 stop
CHS9:10 pmCharleston
$295
Southwest
May 5
CHS7:15 amCharleston
2h 15m
MDW8:30 amChicago Midway
May 9
MDW3:30 pmChicago Midway
2h 05m
CHS6:35 pmCharleston
$297

Delta flights from Charleston to Chicago Midway Airport

Our best Delta deals on Charleston to Chicago Midway Airport flight tickets
Delta
May 5
CHS4:35 pmCharleston
6h 53m
1 stop
MDW10:28 pmChicago Midway
May 9
MDW4:30 pmChicago Midway
4h 09m
1 stop
CHS9:39 pmCharleston
$317
Delta
Feb 28
CHS5:31 pmCharleston
6h 00m
1 stop
MDW10:31 pmChicago Midway
Mar 3
MDW10:49 amChicago Midway
4h 10m
1 stop
CHS3:59 pmCharleston
$392
Delta
Feb 28
CHS5:31 pmCharleston
6h 00m
1 stop
MDW10:31 pmChicago Midway
Mar 4
MDW10:49 amChicago Midway
6h 05m
1 stop
CHS5:54 pmCharleston
$449

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 February 16, 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

CharlestonChicago

CHS - MDW

CHSMDW

Charleston

Tue 5/5

3:26 pm-1:00 pm

1 stop22h 34m

Chicago Midway

Sat 5/9

7:30 am-2:31 pm

1 stop6h 01m

$135

CharlestonChicago

CHS - MDW

CHSMDW

Charleston

Mon 4/27

9:35 am-1:00 pm

1 stop28h 25m

Chicago Midway

Wed 4/29

7:30 am-2:31 pm

1 stop6h 01m

$160

CharlestonChicago

CHS - MDW

CHSMDW

Charleston

Sat 3/7

5:00 pm-12:02 pm

1 stop20h 02m

Chicago Midway

Mon 3/9

9:51 pm-8:38 am

1 stop9h 47m

$169

CharlestonChicago

CHS - MDW

CHSMDW

Charleston

Sat 3/7

5:00 pm-12:02 pm

1 stop20h 02m

Chicago Midway

Mon 3/9

9:51 pm-8:38 am

1 stop9h 47m

$172

CharlestonChicago

CHS - MDW

CHSMDW

Charleston

Tue 5/5

3:26 pm-1:00 pm

1 stop22h 34m

Chicago Midway

Sat 5/9

7:30 am-2:31 pm

1 stop6h 01m

$173

CharlestonChicago

CHS - MDW

CHSMDW

Charleston

Tue 5/5

3:26 pm-1:00 pm

1 stop22h 34m

Chicago Midway

Sat 5/9

7:30 am-2:31 pm

1 stop6h 01m

$180

CharlestonChicago

CHS - MDW

CHSMDW

Charleston

Fri 4/24

3:21 pm-4:13 pm

1 stop25h 52m

Chicago Midway

Mon 4/27

7:30 am-2:31 pm

1 stop6h 01m

$181

CharlestonChicago

CHS - MDW

CHSMDW

Charleston

Sat 3/7

5:00 pm-12:02 pm

1 stop20h 02m

Chicago Midway

Mon 3/9

9:51 pm-4:05 pm

2 stops17h 14m

$187

CharlestonChicago

CHS - MDW

CHSMDW

Charleston

Wed 5/6

3:26 pm-1:00 pm

1 stop22h 34m

Chicago Midway

Fri 5/8

7:30 am-2:31 pm

1 stop6h 01m

$200

CharlestonChicago

CHS - MDW

CHSMDW

Charleston

Mon 3/16

12:04 pm-1:02 pm

1 stop25h 58m

Chicago Midway

Mon 3/23

9:51 pm-8:38 am

1 stop9h 47m

$210

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 month to fly to Chicago Midway Airport?

The month of October is, on average, the cheapest month to fly to Chicago Midway Airport from Charleston, with most prices found around $229. If you are unable to visit Chicago Midway Airport during the month of October, then departing from Charleston during the month July is also very affordable. Most momondo users find prices during this month for around $285.

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 $536.

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 $319 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 23% 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

$232

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 $232. The best round-trip flight deal from Charleston to Chicago Midway Airport found on momondo in the last 72 hours is $316.
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

  • 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
4,289 reviews
Search Southwest flights
DeltaPriceFrom $233Free CancellationRating
7.9
8,205 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 6 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 $349. Our users have rated Southwest at 8.0/10.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Saint Joseph
Portage
Lansing
Schererville
Valparaiso
Munster
Crown Point
Chesterton
Monticello
Porter
Griffith
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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