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Cheap flights from Chicago Midway Airport to Charleston 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 Chicago Midway Airport to Charleston departing on 11/11. 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 Chicago Midway Airport to Charleston

Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
5:56 pm - 11:00 amMDW-CHS
16h 04m1 stop
Multiple Airlines Logo
11:55 am - 11:25 pmCHS-MDW
12h 30m1 stop
$278Multiple Airlines
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Thu, Dec 11 - Sun, Dec 14
Multiple Airlines Logo
1:37 pm - 7:56 amMDW-CHS
17h 19m2 stops
Multiple Airlines Logo
6:11 pm - 11:55 pmCHS-MDW
6h 44m1 stop
$282Multiple Airlines
Find Deal
Fri, Nov 14 - Sun, Nov 16
Multiple Airlines Logo
6:20 am - 5:03 pmMDW-CHS
9h 43m1 stop
Multiple Airlines Logo
6:15 pm - 11:25 pmCHS-MDW
6h 10m1 stop
$285Multiple Airlines
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Thu, Nov 20 - Tue, Dec 2
Southwest Logo
12:45 pm - 3:45 pmMDW-CHS
2h 00mnonstop
Southwest Logo
10:35 am - 1:45 pmCHS-MDW
4h 10m1 stop
$286Southwest
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Fri, Oct 31 - Mon, Nov 3
Southwest Logo
5:35 am - 12:25 pmMDW-CHS
5h 50m1 stop
Southwest Logo
6:10 am - 7:25 amCHS-MDW
2h 15mnonstop
$289Southwest
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Wed, Nov 12 - Sat, Nov 15
Southwest Logo
10:50 am - 8:35 pmMDW-CHS
8h 45m1 stop
Southwest Logo
10:35 am - 1:45 pmCHS-MDW
4h 10m1 stop
$294Southwest
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Tue, Nov 4 - Wed, Nov 5
Multiple Airlines Logo
6:26 pm - 7:56 amMDW-CHS
12h 30m1 stop
Multiple Airlines Logo
9:13 pm - 6:39 pmCHS-MDW
22h 26m2 stops
$295Multiple Airlines
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Thu, Nov 6 - Sun, Nov 9
Delta Logo
10:35 am - 3:38 pmMDW-CHS
4h 03m1 stop
Delta Logo
5:30 am - 9:56 amCHS-MDW
5h 26m1 stop
$299Delta
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Tue, Jan 6 - Sat, Jan 10
Delta Logo
6:00 am - 11:46 amMDW-CHS
4h 46m1 stop
Delta Logo
6:30 am - 9:52 amCHS-MDW
4h 22m1 stop
$306Delta
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Mon, Nov 24 - Fri, Nov 28
Frontier Logo
12:14 pm - 6:52 pmMDW-CHS
5h 38m1 stop
Frontier Logo
10:31 am - 5:11 pmCHS-MDW
7h 40m1 stop
$348Frontier
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Fri, Nov 7 - Sun, Nov 9

Delta flights from Chicago Midway Airport to Charleston

Our best Delta deals on Chicago Midway Airport to Charleston flight tickets
Delta
Jan 6
MDW10:35 amChicago Midway
4h 03m
1 stop
CHS3:38 pmCharleston
Jan 10
CHS5:30 amCharleston
5h 26m
1 stop
MDW9:56 amChicago Midway
$299
Find similar
Delta
Nov 24
MDW6:00 amChicago Midway
4h 46m
1 stop
CHS11:46 amCharleston
Nov 28
CHS6:30 amCharleston
4h 22m
1 stop
MDW9:52 amChicago Midway
$306
Find similar
Delta
Jan 1
MDW9:50 amChicago Midway
4h 20m
1 stop
CHS3:10 pmCharleston
Jan 4
CHS5:25 amCharleston
4h 40m
1 stop
MDW9:05 amChicago Midway
$320
Find similar

Southwest flights from Chicago Midway Airport to Charleston

Our best Southwest deals on Chicago Midway Airport to Charleston flight tickets
Southwest
Oct 31
MDW12:45 pmChicago Midway
2h 00m
CHS3:45 pmCharleston
Nov 3
CHS10:35 amCharleston
4h 10m
1 stop
MDW1:45 pmChicago Midway
$286
Find similar
Southwest
Nov 12
MDW5:35 amChicago Midway
5h 50m
1 stop
CHS12:25 pmCharleston
Nov 15
CHS6:10 amCharleston
2h 15m
MDW7:25 amChicago Midway
$289
Find similar
Southwest
Nov 4
MDW10:50 amChicago Midway
8h 45m
1 stop
CHS8:35 pmCharleston
Nov 5
CHS10:35 amCharleston
4h 10m
1 stop
MDW1:45 pmChicago Midway
$294
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago Midway Airport to Charleston 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 October 14, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Charleston that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoCharleston

MDW - CHS

MDWCHS

Chicago Midway

Thu 12/11

5:56 pm-11:00 am

1 stop16h 04m

Charleston

Sun 12/14

11:55 am-11:25 pm

1 stop12h 30m

$278

ChicagoCharleston

MDW - CHS

MDWCHS

Chicago Midway

Fri 11/14

1:37 pm-7:56 am

2 stops17h 19m

Charleston

Sun 11/16

6:11 pm-11:55 pm

1 stop6h 44m

$282

ChicagoCharleston

MDW - CHS

MDWCHS

Chicago Midway

Thu 11/20

6:20 am-5:03 pm

1 stop9h 43m

Charleston

Tue 12/2

6:15 pm-11:25 pm

1 stop6h 10m

$285

ChicagoCharleston

MDW - CHS

MDWCHS

Chicago Midway

Fri 10/31

12:45 pm-3:45 pm

Nonstop2h 00m

Charleston

Mon 11/3

10:35 am-1:45 pm

1 stop4h 10m

$286

ChicagoCharleston

MDW - CHS

MDWCHS

Chicago Midway

Wed 11/12

5:35 am-12:25 pm

1 stop5h 50m

Charleston

Sat 11/15

6:10 am-7:25 am

Nonstop2h 15m

$289

ChicagoCharleston

MDW - CHS

MDWCHS

Chicago Midway

Tue 11/4

10:50 am-8:35 pm

1 stop8h 45m

Charleston

Wed 11/5

10:35 am-1:45 pm

1 stop4h 10m

$294

ChicagoCharleston

MDW - CHS

MDWCHS

Chicago Midway

Thu 11/6

6:26 pm-7:56 am

1 stop12h 30m

Charleston

Sun 11/9

9:13 pm-6:39 pm

2 stops22h 26m

$295

ChicagoCharleston

MDW - CHS

MDWCHS

Chicago Midway

Tue 1/6

10:35 am-3:38 pm

1 stop4h 03m

Charleston

Sat 1/10

5:30 am-9:56 am

1 stop5h 26m

$299

ChicagoCharleston

MDW - CHS

MDWCHS

Chicago Midway

Mon 11/24

6:00 am-11:46 am

1 stop4h 46m

Charleston

Fri 11/28

6:30 am-9:52 am

1 stop4h 22m

$306

ChicagoCharleston

MDW - CHS

MDWCHS

Chicago Midway

Fri 11/7

12:14 pm-6:52 pm

1 stop5h 38m

Charleston

Sun 11/9

10:31 am-5:11 pm

1 stop7h 40m

$348

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 Charleston from

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

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 Charleston?

The cheapest month to fly to Charleston from Chicago Midway Airport is in May. Flight prices, which tend to average around $302, are often lower during this time because this is during the off-season. The month of August is another great option to travel to Charleston, with average flight prices from Chicago Midway Airport averaging around $307.

What is the cheapest day to depart on your flight to Charleston?

The cheapest day to depart from Chicago Midway Airport to Charleston is on a Tuesday. Travelers who choose to depart for Charleston on a Tuesday will often find tickets for as low as $360. The most expensive day to fly to Charleston is Sunday, with ticket prices averaging around $418.

What is the cheapest time of day to depart on your flight to Charleston?

The cheapest time of day to fly to Charleston is at noon when flights can be purchased for as low as $354. In the afternoon is when there is more demand to fly to Charleston, so prices are often more expensive at around $398 per ticket.

What is the cheapest Chicago Midway to Charleston flight route?

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

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

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

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

When to book flights from Chicago Midway Airport to Charleston

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

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

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

Best Price Found

$329

Fastest flight time

2h 00m

Direct flights

Every day

Airports in Charleston

1 airport
The best one-way flight to Charleston from Chicago Midway Airport in the past 72 hours is $329. The best round-trip flight deal from Chicago Midway Airport to Charleston found on momondo in the last 72 hours is $429.
The fastest flight from Chicago Midway Airport to Charleston takes 2h 00m
Direct flights go from Chicago Midway Airport to Charleston every day.
There is 1 airport near Charleston: Charleston (CHS)
Search flight deals

  • How far is Chicago Midway to Charleston by plane?

    Charleston is 755.1 mi away from Chicago Midway. In terms of flight time, this usually takes a little over 2h 00m.

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

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

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

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

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Chicago Midway Airport to Charleston Airport.

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

    The required travel and health documents for your Charleston 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 Charleston 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 Chicago Midway Airport to Charleston?

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

Best airlines flying from Chicago Midway Airport to Charleston

Compare and see reviews for airlines that fly from Chicago Midway Airport to Charleston with momondo
Airline
Rating
Free Cancellation
Price
SouthwestPriceFrom $257Free CancellationRating
8.0
4,238 reviews
Search Southwest flights

  • Southwest Flights From Chicago Midway Airport to Charleston

    Southwest is one of the most popular airlines flying from Chicago Midway Airport to Charleston, operating 5 flights/week on average for this route. A good Southwest flight deal for Chicago Midway Airport to Charleston starts from $257 round-trip, up to an average price of $359. Our users have rated Southwest at 8.0/10.

Traveling to a place near Charleston?

Book flights to Charleston if you plan to visit one of these locations
Folly Beach
Isle of Palms
North Charleston
Kiawah Island
Summerville
Mount Pleasant
Edisto Island
Santee
Walterboro
Goose Creek
Edisto Beach
Seabrook Island

Why use momondo?

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

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Charleston from Chicago.

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

Yes. momondo enables you to select and highlight flights to Charleston from Chicago with this policy.

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

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Chicago to Charleston.

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

Yes. momondo can track prices for Chicago to Charleston 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 Charleston trip

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