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Cheap flights from Chicago Midway Airport to Charleston from $103

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 5/26. 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.
Southwest Logo
12:50 pm - 8:25 pm
MDW
-
CHS
6h 35m
2 stops
Southwest Logo
4:45 pm - 7:35 pm
CHS
-
MDW
3h 50m
1 stop
$265Southwest
Wed, Jun 3 - Mon, Jun 8
Southwest Logo
3:30 pm - 6:35 pm
MDW
-
CHS
2h 05mnonstop
Southwest Logo
7:15 am - 8:30 am
CHS
-
MDW
2h 15mnonstop
$266Southwest
Sat, May 16 - Wed, May 20
Southwest Logo
6:00 pm - 9:05 pm
MDW
-
CHS
2h 05mnonstop
Southwest Logo
5:55 pm - 7:10 pm
CHS
-
MDW
2h 15mnonstop
$268Southwest
Wed, Jun 3 - Mon, Jun 8
Southwest Logo
6:50 pm - 9:55 pm
MDW
-
CHS
2h 05mnonstop
Southwest Logo
3:40 pm - 9:50 pm
CHS
-
MDW
7h 10m
1 stop
$270Southwest
Mon, May 11 - Wed, May 13
Southwest Logo
6:10 pm - 9:15 pm
MDW
-
CHS
2h 05mnonstop
Southwest Logo
4:45 pm - 7:35 pm
CHS
-
MDW
3h 50m
1 stop
$272Southwest
Sat, Jun 6 - Mon, Jun 8
Southwest Logo
6:20 pm - 9:25 pm
MDW
-
CHS
2h 05mnonstop
Southwest Logo
2:10 pm - 5:05 pm
CHS
-
MDW
3h 55m
1 stop
$273Southwest
Wed, Jun 10 - Tue, Jun 30
Southwest Logo
6:00 pm - 9:05 pm
MDW
-
CHS
2h 05mnonstop
Southwest Logo
7:15 am - 8:30 am
CHS
-
MDW
2h 15mnonstop
$274Southwest
Tue, May 19 - Tue, May 26
Southwest Logo
3:00 pm - 8:00 pm
MDW
-
CHS
4h 00m
1 stop
Southwest Logo
7:40 am - 8:55 am
CHS
-
MDW
2h 15mnonstop
$275Southwest
Tue, May 26 - Fri, May 29
Southwest Logo
7:45 pm - 10:50 pm
MDW
-
CHS
2h 05mnonstop
Southwest Logo
5:55 pm - 7:10 pm
CHS
-
MDW
2h 15mnonstop
$276Southwest
Thu, Jun 4 - Mon, Jun 8
Southwest Logo
7:20 am - 3:55 pm
MDW
-
CHS
7h 35m
2 stops
Southwest Logo
7:00 am - 8:10 am
CHS
-
MDW
2h 10mnonstop
$277Southwest
Sat, Aug 22 - Mon, Aug 24

Southwest flights from Chicago Midway Airport to Charleston

Our best Southwest deals on Chicago Midway Airport to Charleston flight tickets
Southwest
Jun 3
MDW12:50 pmChicago Midway
6h 35m
2 stops
CHS8:25 pmCharleston
Jun 8
CHS4:45 pmCharleston
3h 50m
1 stop
MDW7:35 pmChicago Midway
$265
Southwest
May 16
MDW3:30 pmChicago Midway
2h 05m
CHS6:35 pmCharleston
May 20
CHS7:15 amCharleston
2h 15m
MDW8:30 amChicago Midway
$266
Southwest
Jun 3
MDW6:00 pmChicago Midway
2h 05m
CHS9:05 pmCharleston
Jun 8
CHS5:55 pmCharleston
2h 15m
MDW7:10 pmChicago Midway
$268

Delta flights from Chicago Midway Airport to Charleston

Our best Delta deals on Chicago Midway Airport to Charleston flight tickets
Delta
May 27
MDW10:59 amChicago Midway
3h 50m
1 stop
CHS3:49 pmCharleston
Jun 3
CHS6:15 amCharleston
4h 45m
1 stop
MDW10:00 amChicago Midway
$285
Delta
May 28
MDW6:23 amChicago Midway
6h 40m
1 stop
CHS2:03 pmCharleston
Jun 3
CHS6:15 amCharleston
4h 45m
1 stop
MDW10:00 amChicago Midway
$294
Delta
May 11
MDW5:10 pmChicago Midway
4h 46m
1 stop
CHS10:56 pmCharleston
May 14
CHS6:15 amCharleston
4h 45m
1 stop
MDW10:00 amChicago Midway
$295

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 April 24, 2026.
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

Cheapest round-trip

ChicagoCharleston

MDW - CHS

MDWCHS

Chicago Midway

Wed 6/3

12:50 pm-8:25 pm

2 stops6h 35m

Charleston

Mon 6/8

4:45 pm-7:35 pm

1 stop3h 50m

$265
Quickest round-trip

ChicagoCharleston

MDW - CHS

MDWCHS

Chicago Midway

Sat 5/16

3:30 pm-6:35 pm

Nonstop2h 05m

Charleston

Wed 5/20

7:15 am-8:30 am

Nonstop2h 15m

$266

ChicagoCharleston

MDW - CHS

MDWCHS

Chicago Midway

Wed 6/3

6:00 pm-9:05 pm

Nonstop2h 05m

Charleston

Mon 6/8

5:55 pm-7:10 pm

Nonstop2h 15m

$268

ChicagoCharleston

MDW - CHS

MDWCHS

Chicago Midway

Mon 5/11

6:50 pm-9:55 pm

Nonstop2h 05m

Charleston

Wed 5/13

3:40 pm-9:50 pm

1 stop7h 10m

$270

ChicagoCharleston

MDW - CHS

MDWCHS

Chicago Midway

Sat 6/6

6:10 pm-9:15 pm

Nonstop2h 05m

Charleston

Mon 6/8

4:45 pm-7:35 pm

1 stop3h 50m

$272

ChicagoCharleston

MDW - CHS

MDWCHS

Chicago Midway

Wed 6/10

6:20 pm-9:25 pm

Nonstop2h 05m

Charleston

Tue 6/30

2:10 pm-5:05 pm

1 stop3h 55m

$273

ChicagoCharleston

MDW - CHS

MDWCHS

Chicago Midway

Tue 5/19

6:00 pm-9:05 pm

Nonstop2h 05m

Charleston

Tue 5/26

7:15 am-8:30 am

Nonstop2h 15m

$274

ChicagoCharleston

MDW - CHS

MDWCHS

Chicago Midway

Tue 5/26

3:00 pm-8:00 pm

1 stop4h 00m

Charleston

Fri 5/29

7:40 am-8:55 am

Nonstop2h 15m

$275

ChicagoCharleston

MDW - CHS

MDWCHS

Chicago Midway

Thu 6/4

7:45 pm-10:50 pm

Nonstop2h 05m

Charleston

Mon 6/8

5:55 pm-7:10 pm

Nonstop2h 15m

$276

ChicagoCharleston

MDW - CHS

MDWCHS

Chicago Midway

Sat 8/22

7:20 am-3:55 pm

2 stops7h 35m

Charleston

Mon 8/24

7:00 am-8:10 am

Nonstop2h 10m

$277

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

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 $338. The most expensive day to fly to Charleston is Sunday, with ticket prices averaging around $396.

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

The cheapest time of day to fly to Charleston is in the evening when flights can be purchased for as low as $366. In the morning is when there is more demand to fly to Charleston, so prices are often more expensive at around $378 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 Airport to Charleston flights?

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

$194

Fastest flight time

2h 05m

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 $194. The best round-trip flight deal from Chicago Midway Airport to Charleston found on momondo in the last 72 hours is $377.
The fastest flight from Chicago Midway Airport to Charleston takes 2h 05m
Direct flights go from Chicago Midway Airport to Charleston every day.
There is 1 airport in Charleston. From Chicago Midway Airport there are direct flights to Charleston (CHS).
Search flight deals

Frequently asked questions about flying from Chicago Midway Airport to Charleston

  • 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 05m.

  • 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 $153Free CancellationRating
8.0
4,334 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 8 flights/week on average for this route. A good Southwest flight deal for Chicago Midway Airport to Charleston starts from $153 round-trip, up to an average price of $377. 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
Summerville
Kiawah Island
North Charleston
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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