MDW - CHS

$76 Find Cheap Flights from Chicago Midway Airport to Charleston

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Midway to Charleston departing on 4/14. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Charleston

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Charleston, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Charleston, as well as popular online travel agencies
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

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Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Everything you should know

Cheapest round-trip
$284
Southwest
Sat 4/4Tue 4/14
MDW - CHS • 2 stops
Cheapest non-stop
$293
Southwest
Fri 5/8Mon 5/11
MDW - CHS • Non-stop
Advice from real travelers
AI-powered summary based on content written by travel experts. AI can make mistakes.
Midway's compact terminal offers easy navigation.
Use rideshare for a cost-effective trip from CHS.
Expert advice
Expert advice
Expert advice
Expert advice
Top airlines
Southwest
Cheapest • from $284 (round-trip)
Southwest
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
Every day
You can fly direct with Southwest. Average duration is 2h 05m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Top layover airports
Fort Lauderdale (FLL)
Cheapest • Avg $374 (round-trip)
Atlanta (ATL)
Shortest trip • 4h 25m (one-way)
Insights
Insights
Insights
Insights
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KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Charleston!
Flight Deals
Booking Insights
Expert advice
Flight Deals

Cheap Flights from Midway to Charleston (MDW-CHS)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Midway to Charleston that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Midway to Charleston

Sat, Apr 4 - Tue, Apr 14
Southwest Logo
12:35 pm - 12:10 am
MDW
-
CHS
10h 35m
2 stops
Southwest Logo
7:40 am - 2:20 pm
CHS
-
MDW
7h 40m
2 stops
$284Southwest
Mon, Jun 1 - Thu, Jun 4
Southwest Logo
7:30 am - 2:15 pm
MDW
-
CHS
5h 45m
1 stop
Southwest Logo
7:15 am - 1:45 pm
CHS
-
MDW
7h 30m
2 stops
$290Southwest
Fri, May 1 - Tue, May 5
Southwest Logo
6:50 pm - 9:55 pm
MDW
-
CHS
2h 05mnonstop
Southwest Logo
12:00 pm - 7:45 pm
CHS
-
MDW
8h 45m
2 stops
$291Southwest
Fri, May 8 - Mon, May 11
Southwest Logo
6:50 pm - 9:55 pm
MDW
-
CHS
2h 05mnonstop
Southwest Logo
7:40 am - 8:55 am
CHS
-
MDW
2h 15mnonstop
$293Southwest
Wed, Apr 29 - Sun, May 3
Multiple Airlines Logo
2:15 pm - 4:25 pm
MDW
-
CHS
25h 10m
2 stops
Multiple Airlines Logo
10:48 pm - 7:46 am
CHS
-
MDW
9h 58m
1 stop
$295Multiple Airlines
Sat, Apr 4 - Mon, Apr 6
Southwest Logo
12:35 pm - 12:10 am
MDW
-
CHS
10h 35m
2 stops
Southwest Logo
8:55 pm - 12:05 am
CHS
-
MDW
4h 10m
1 stop
$296Southwest
Sat, Apr 4 - Tue, Apr 14
Southwest Logo
12:45 pm - 3:50 pm
MDW
-
CHS
2h 05mnonstop
Southwest Logo
7:15 am - 8:30 am
CHS
-
MDW
2h 15mnonstop
$299Southwest
Fri, May 1 - Tue, May 5
Southwest Logo
7:30 am - 5:05 pm
MDW
-
CHS
8h 35m
1 stop
Southwest Logo
7:40 am - 2:05 pm
CHS
-
MDW
7h 25m
2 stops
$301Southwest
Fri, May 8 - Mon, May 11
Southwest Logo
8:55 am - 5:05 pm
MDW
-
CHS
7h 10m
1 stop
Southwest Logo
7:40 am - 8:55 am
CHS
-
MDW
2h 15mnonstop
$303Southwest
Wed, Apr 29 - Wed, May 6
Southwest Logo
6:00 pm - 9:05 pm
MDW
-
CHS
2h 05mnonstop
Southwest Logo
7:15 am - 8:30 am
CHS
-
MDW
2h 15mnonstop
$306Southwest
Booking Insights

KAYAK's insights & trends for Midway to Charleston flights

Get data-powered insights and trends into flights from Midway to Charleston to help you find the cheapest flights, the best time to fly and much more.

What’s the cheapest day of the week to fly from Chicago Midway Airport to Charleston?

The average price of all round-trip flights from Chicago Midway Airport to Charleston clicked on KAYAK for each day over the last 12 months.

When flying from Chicago Midway Airport to Charleston, you should consider leaving on a Tuesday and avoid Thursdays if you are looking for the best rates. For your return to Chicago Midway Airport, you’ll find the best rates on Thursdays and the most expensive ones on Sundays.

Can I save money by flying with a layover from Chicago Midway Airport to Charleston?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 1 stop layover the cheapest option at $548 on average.

Find deals
Expert advice

Expert advice for your flight from Midway to Charleston

 
AI-powered summary based on content written by travel experts. AI can make mistakes.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Our travel experts
Stefanie Waldek

Stefanie Waldek

Expert on MDW

Stefanie Waldek is a freelance space, travel, and design writer based in Saratoga Springs, NY. Her words have appeared in Space.com, Travel + Leisure, Condé Nast Traveler, Architectural Digest, and House Beautiful, among other publications. An expert in aviation and expedition cruising, Stefanie is frequently up in the air or on the sea, likely en route to Antarctica or the Arctic.

Read more
Brandon Schultz

Brandon Schultz

Expert on CHS

Brandon Schultz is an award-winning food and travel writer based in New York City. His work has appeared in Forbes, AAA, Thrillist, Travel + Leisure, and The Daily Meal, among many others, and he is the author of 6 books, including 3 cookbooks.

Read more

Good to know

Low seasonOctober
Cheapest flight$76
Best time to beat the crowds with an average 34% drop in price.
Most popular time to fly and prices are also 15% lower on average.
Flight from Chicago Midway Airport to Charleston

When to book flights from Midway to Charleston

Are your dates flexible? Find out the best times to travel from Midway to Charleston based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Chicago Midway Airport to Charleston flights

  • What is the cheapest flight from Chicago Midway Airport to Charleston?

    In the last 3 days, the lowest price for a flight from Chicago Midway Airport to Charleston was $76 for a one-way ticket and $284 for a round-trip.

  • Do I need a passport to fly between Chicago Midway Airport and Charleston?

    A passport is not required to fly from Chicago Midway Airport to Charleston.

  • Which airports will I be using when flying from Chicago Midway Airport to Charleston?

    Chicago Midway Airport airport is called Chicago Midway and the only airport in Charleston is Charleston.

  • Which airlines offer Wi-Fi service onboard planes from Chicago Midway Airport to Charleston?

    Only American Airlines offers inflight Wi-Fi service on the Chicago Midway Airport to Charleston flight route.

  • Which aircraft models fly most regularly from Chicago Midway Airport to Charleston?

    The Airbus A319 is the aircraft model that flies most regularly on the Chicago Midway Airport to Charleston flight route.

  • On which days can I fly direct from Chicago Midway Airport to Charleston?

    There are nonstop flights from Chicago Midway Airport to Charleston on a daily basis.

  • How does KAYAK find such low prices on flights from Chicago Midway Airport to Charleston?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago Midway Airport to Charleston.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago Midway Airport to Charleston?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Charleston from Chicago Midway Airport is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago Midway Airport to Charleston?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Charleston with an airline and back to Chicago Midway Airport with another airline. Booking your flights between Chicago Midway Airport and CHS can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago Midway Airport to Charleston?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Charleston from Chicago Midway Airport up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

KAYAK’s top tips for finding a cheap flight from Chicago Midway Airport to Charleston

  • Looking for a cheap flight? 25% of our users found flights on this route for $369 or less round-trip.

Prefer to fly direct from Chicago Midway Airport to Charleston?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Chicago Midway to Charleston.
Find which airlines fly direct from Chicago Midway Airport to Charleston Airport, which days they fly and book direct flights.

Direct departures

Chicago Midway to Charleston

Monday

Southwest

Southwest

Tuesday

Southwest

Southwest

Wednesday

Southwest

Southwest

Thursday

Southwest

Southwest

Friday

Southwest

Southwest

Saturday

Southwest

Southwest

Sunday

Southwest

Southwest

See more direct flights

Direct returns

Charleston to Chicago Midway

Monday

Southwest

Southwest

Tuesday

Southwest

Southwest

Wednesday

Southwest

Southwest

Thursday

Southwest

Southwest

Friday

Southwest

Southwest

Saturday

Southwest

Southwest

Sunday

Southwest

Southwest

See more direct flights

Reviews of the top airline flying from Midway to Charleston

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Charleston. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Midway to Charleston? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
SouthwestOverall score based on 4318 reviews
8.1Boarding
8.6Crew
7.5Entertainment
8.0Comfort
7.0Food
Airline reviews

Long layover between flights to Long Island from BWI - need better coordination between flights

4.0 OkayKenny, Mar 2026
TPA - BWI
Read more Southwest reviews

Long layover between flights to Long Island from BWI - need better coordination between flights

I elected to pay for the upgrades and found very little difference

The new seating arrangement is so over priced for what you get.

The problem with the seat assignments is that there were a lot of rows in the front that were empty but my row at the back was full. Just not so pleasant.

No food or entertainment, just a quick 40 minute flight. A little bumpy due to Santa Ana winds but pilot has no control over that. Good flight and landing!

Good but I prefer choose your own seat. With the new assigned seats they should board from the back I see no advantage to this new boarding. Just like every other airline

I realize they are still working out kinks with the new boarding process, but by the time I boarded in group 5, most of the bins were full. All airlines should better enforce small bags and jackets going under the seats until everyone has boarded.

WiFi was not working and didn’t have a beverage service

Snacks are always pretzels. Why can't you also offer peanuts ?

Flight boarded late after announcing on time boarding. Flight arrived only a little late despite late departure. Had trouble connecting to WiFi

Everything you need to know for your flight from Midway to Charleston

Information on your arrival and departure airports

Chicago Midway Airport (MDW)
Charleston (CHS)