Latest deals
Insights
When to book
FAQs
Reviews
Price Alerts

Cheap flights from Charleston to Chicago from $69

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 12/3. 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

Discover deals from 900+ travel sites with momondo.

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

Find the cheapest flights from Charleston to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
6:13 pm - 11:42 amCHS-MDW
18h 29m1 stop
Multiple Airlines Logo
6:20 am - 10:05 pmMDW-CHS
14h 45m2 stops
$216Multiple Airlines
Find Deal
Mon, Nov 24 - Thu, Nov 27
Multiple Airlines Logo
6:15 pm - 11:42 amCHS-MDW
18h 27m1 stop
Multiple Airlines Logo
5:47 pm - 8:37 amMDW-CHS
13h 50m1 stop
$219Multiple Airlines
Find Deal
Sat, Nov 22 - Mon, Nov 24
Multiple Airlines Logo
11:55 am - 1:01 pmCHS-MDW
26h 06m1 stop
Multiple Airlines Logo
3:52 pm - 8:37 amMDW-CHS
15h 45m2 stops
$230Multiple Airlines
Find Deal
Sat, Dec 13 - Mon, Dec 15
Frontier Logo
10:32 am - 7:31 pmCHS-MDW
9h 59m1 stop
Frontier Logo
8:04 pm - 8:27 amMDW-CHS
11h 23m1 stop
$232Frontier
Find Deal
Fri, Nov 21 - Sun, Nov 23
Multiple Airlines Logo
6:15 pm - 11:42 amCHS-MDW
18h 27m1 stop
Multiple Airlines Logo
5:47 pm - 8:37 amMDW-CHS
13h 50m1 stop
$234Multiple Airlines
Find Deal
Sat, Nov 22 - Mon, Nov 24
Frontier Logo
1:13 pm - 12:13 amCHS-MDW
12h 00m1 stop
Frontier Logo
8:29 pm - 8:27 amMDW-CHS
10h 58m1 stop
$238Frontier
Find Deal
Tue, Nov 25 - Sat, Nov 29
Delta Logo
5:27 am - 9:58 amCHS-MDW
5h 31m1 stop
Delta Logo
12:46 pm - 7:58 pmMDW-CHS
6h 12m1 stop
$267Delta
Find Deal
Tue, Mar 3 - Wed, Mar 4
Delta Logo
6:30 am - 10:34 amCHS-MDW
5h 04m1 stop
Delta Logo
9:34 am - 5:43 pmMDW-CHS
7h 09m1 stop
$289Delta
Find Deal
Tue, Jan 13 - Mon, Jan 26
Southwest Logo
10:35 am - 1:45 pmCHS-MDW
4h 10m1 stop
Southwest Logo
1:40 pm - 4:40 pmMDW-CHS
2h 00mnonstop
$323Southwest
Find Deal
Tue, Dec 16 - Thu, Dec 18
Southwest Logo
7:30 pm - 8:45 pmCHS-MDW
2h 15mnonstop
Southwest Logo
2:45 pm - 5:45 pmMDW-CHS
2h 00mnonstop
$324Southwest
Find Deal
Fri, Feb 13 - Sun, Feb 15

Frontier flights from Charleston to Chicago Midway Airport

Our best Frontier deals on Charleston to Chicago Midway Airport flight tickets
Frontier
Nov 21
CHS10:32 amCharleston
9h 59m
1 stop
MDW7:31 pmChicago Midway
Nov 23
MDW8:04 pmChicago Midway
11h 23m
1 stop
CHS8:27 amCharleston
$232
Find similar
Frontier
Nov 25
CHS1:13 pmCharleston
12h 00m
1 stop
MDW12:13 amChicago Midway
Nov 29
MDW8:29 pmChicago Midway
10h 58m
1 stop
CHS8:27 amCharleston
$238
Find similar
Frontier
Nov 21
CHS10:32 amCharleston
9h 59m
1 stop
MDW7:31 pmChicago Midway
Nov 23
MDW8:04 pmChicago Midway
11h 23m
1 stop
CHS8:27 amCharleston
$302
Find similar

Delta flights from Charleston to Chicago Midway Airport

Our best Delta deals on Charleston to Chicago Midway Airport flight tickets
Delta
Mar 3
CHS5:27 amCharleston
5h 31m
1 stop
MDW9:58 amChicago Midway
Mar 4
MDW12:46 pmChicago Midway
6h 12m
1 stop
CHS7:58 pmCharleston
$267
Find similar
Delta
Jan 13
CHS6:30 amCharleston
5h 04m
1 stop
MDW10:34 amChicago Midway
Jan 26
MDW9:34 amChicago Midway
7h 09m
1 stop
CHS5:43 pmCharleston
$289
Find similar
Delta
Nov 24
CHS10:40 amCharleston
6h 59m
1 stop
MDW4:39 pmChicago Midway
Nov 27
MDW10:47 amChicago Midway
5h 36m
1 stop
CHS5:23 pmCharleston
$299
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 November 9, 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

Mon 11/24

6:13 pm-11:42 am

1 stop18h 29m

Chicago Midway

Thu 11/27

6:20 am-10:05 pm

2 stops14h 45m

$216

CharlestonChicago

CHS - MDW

CHSMDW

Charleston

Sat 11/22

6:15 pm-11:42 am

1 stop18h 27m

Chicago Midway

Mon 11/24

5:47 pm-8:37 am

1 stop13h 50m

$219

CharlestonChicago

CHS - MDW

CHSMDW

Charleston

Sat 12/13

11:55 am-1:01 pm

1 stop26h 06m

Chicago Midway

Mon 12/15

3:52 pm-8:37 am

2 stops15h 45m

$230

CharlestonChicago

CHS - MDW

CHSMDW

Charleston

Fri 11/21

10:32 am-7:31 pm

1 stop9h 59m

Chicago Midway

Sun 11/23

8:04 pm-8:27 am

1 stop11h 23m

$232

CharlestonChicago

CHS - MDW

CHSMDW

Charleston

Sat 11/22

6:15 pm-11:42 am

1 stop18h 27m

Chicago Midway

Mon 11/24

5:47 pm-8:37 am

1 stop13h 50m

$234

CharlestonChicago

CHS - MDW

CHSMDW

Charleston

Tue 11/25

1:13 pm-12:13 am

1 stop12h 00m

Chicago Midway

Sat 11/29

8:29 pm-8:27 am

1 stop10h 58m

$238

CharlestonChicago

CHS - MDW

CHSMDW

Charleston

Tue 3/3

5:27 am-9:58 am

1 stop5h 31m

Chicago Midway

Wed 3/4

12:46 pm-7:58 pm

1 stop6h 12m

$267

CharlestonChicago

CHS - MDW

CHSMDW

Charleston

Tue 1/13

6:30 am-10:34 am

1 stop5h 04m

Chicago Midway

Mon 1/26

9:34 am-5:43 pm

1 stop7h 09m

$289

CharlestonChicago

CHS - MDW

CHSMDW

Charleston

Tue 12/16

10:35 am-1:45 pm

1 stop4h 10m

Chicago Midway

Thu 12/18

1:40 pm-4:40 pm

Nonstop2h 00m

$323

CharlestonChicago

CHS - MDW

CHSMDW

Charleston

Fri 2/13

7:30 pm-8:45 pm

Nonstop2h 15m

Chicago Midway

Sun 2/15

2:45 pm-5:45 pm

Nonstop2h 00m

$324

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

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 $321. 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 $522.

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 $446. 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 77% 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

$188

Fastest flight time

2h 15m

Direct flights

Mon, Tue, Wed, Fri, Sat and Sun
The best one-way flight to Chicago Midway Airport from Charleston in the past 72 hours is $188. The best round-trip flight deal from Charleston to Chicago Midway Airport found on momondo in the last 72 hours is $322.
The fastest flight from Charleston to Chicago Midway Airport takes 2h 15m
Direct flights go from Charleston to Chicago Midway Airport on Monday, Tuesday, Wednesday, 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
8.0
4,240 reviews
Search Southwest flights
DeltaPriceFrom $368Free CancellationRating
7.9
8,002 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 9 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 $361. 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
Crown Point
Munster
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.

An easier way to manage your Chicago Midway Airport trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Tue 12/9
Tue 12/16
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Chicago