MDW - CHS

$119 Find Cheap Flights from Chicago Midway Airport to Charleston - Compare and Save

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 7/28. 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

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Everything you should know

Cheapest round-trip
$269
Typical prices: $294-$508
Southwest
Thu 8/27Mon 8/31
MDW - CHS • Non-stop
Cheapest one-way
$119
Southwest
Tue 7/28
MDW - CHS • Non-stop
Top airlines
Southwest
Cheapest • from $268 (round-trip)
Southwest
Best reviews • 7.9 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 10m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Top layover airports
Atlanta (ATL)
Cheapest • Avg $338 (round-trip)
Atlanta (ATL)
Shortest trip • 4h 19m (one-way)
Insights
Insights
Insights
Insights
When to travel
January
Cheapest • 100% price drop
May
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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Flight Deals
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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

Thu, Aug 27 - Mon, Aug 31
Southwest Logo
7:35 am - 10:55 am
MDW
-
CHS
2h 20mnonstop
Southwest Logo
6:30 pm - 7:40 pm
CHS
-
MDW
2h 10mnonstop
$269Southwest
Wed, Sep 16 - Mon, Sep 21
Delta Logo
6:05 am - 1:05 pm
MDW
-
CHS
6h 00m
1 stop
Delta Logo
5:33 pm - 10:45 pm
CHS
-
MDW
6h 12m
1 stop
$273Delta
Mon, Aug 17 - Sat, Aug 22
Southwest Logo
10:30 am - 7:10 pm
MDW
-
CHS
7h 40m
2 stops
Southwest Logo
1:20 pm - 7:10 pm
CHS
-
MDW
6h 50m
1 stop
$278Southwest
Thu, Aug 13 - Thu, Aug 20
Southwest Logo
6:15 pm - 9:25 pm
MDW
-
CHS
2h 10mnonstop
Southwest Logo
7:15 pm - 10:20 pm
CHS
-
MDW
4h 05m
1 stop
$279Southwest
Wed, Sep 30 - Mon, Oct 5
Southwest Logo
6:00 pm - 9:10 pm
MDW
-
CHS
2h 10mnonstop
Southwest Logo
7:25 pm - 8:35 pm
CHS
-
MDW
2h 10mnonstop
$281Southwest
Sat, Aug 8 - Mon, Aug 10
Southwest Logo
6:45 am - 6:50 pm
MDW
-
CHS
11h 05m
2 stops
Southwest Logo
6:35 am - 12:15 pm
CHS
-
MDW
6h 40m
2 stops
$283Southwest
Thu, Aug 13 - Thu, Aug 20
Southwest Logo
7:35 am - 10:55 am
MDW
-
CHS
2h 20mnonstop
Southwest Logo
11:30 am - 6:55 pm
CHS
-
MDW
8h 25m
2 stops
$284Southwest
Thu, Oct 15 - Sat, Oct 17
Southwest Logo
2:45 pm - 12:05 am
MDW
-
CHS
8h 20m
1 stop
Southwest Logo
8:30 am - 9:40 am
CHS
-
MDW
2h 10mnonstop
$287Southwest
Thu, Sep 24 - Mon, Sep 28
Delta Logo
10:48 am - 5:46 pm
MDW
-
CHS
5h 58m
1 stop
Delta Logo
5:25 am - 9:50 am
CHS
-
MDW
5h 25m
1 stop
$289Delta
Thu, Aug 13 - Thu, Aug 20
Southwest Logo
1:00 pm - 8:30 pm
MDW
-
CHS
6h 30m
1 stop
Southwest Logo
8:40 am - 2:55 pm
CHS
-
MDW
7h 15m
2 stops
$294Southwest
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 Wednesdays and the most expensive ones on Sundays.

What is the cheapest month to fly from Chicago Midway Airport to Charleston?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago Midway Airport to Charleston, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Chicago Midway Airport to Charleston is January, where tickets cost $0 (return) on average. On the other hand, the most expensive months are March and April, where the average cost of round-trip tickets is $585 and $570 respectively.

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.

No, with an average price for the route of $355, prices are generally cheapest when you fly direct.

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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$119
Best time to beat the crowds with an average 40% drop in price.
Most popular time to fly and prices are also 2% 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 5 days, the lowest price for a flight from Chicago Midway Airport to Charleston was $119 for a one-way ticket and $268 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 Boeing 737-800 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 $323 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.
7.9
SouthwestOverall score based on 4250 reviews
8.1Boarding
8.0Comfort
8.6Crew
7.0Food
7.5Entertainment
Airline reviews

OKay. I sat in the back of the plane and it was really loud between babies and little kids, and adults who.like to talk a lot and loudly most of the flight.

6.0 GoodAnonymous, Jun 2026
MDW - BDL
Read more Southwest reviews

OKay. I sat in the back of the plane and it was really loud between babies and little kids, and adults who.like to talk a lot and loudly most of the flight.

The first time I flew in the extra legroom section. It was difficult to notice a difference. I had bad luck with my neighbors. The crew was okay. Southwest has reduced the live TV options.

I flew twice this week on Southwest, was delayed over 2 hours both ways. From Pittsburgh to Chicago it was due to weather but the gate agents, pilot etc were great at updating everyone. Today from Midway to Pittsburgh the plane had come from an international location, kept getting delayed, no information was given until we were delayed for the third time. It was ridiculous, whoever scheduled that plane to fly to Pittsburgh after didn’t consider a lot of things.

The staff was very friendly, professional, and courteous. The overall flight was a great experience.

Check-in, Boarding and flight were smooth. All the employees and crew was very nice and funny. They gave the kids crayons and workbooks to keep them occupied which was a big win. I’ve flown Southwest many times and that’s the first time I’ve seen that and it is a great addition.

All was good. I just had a hard time getting connected to the WiFi/internet during the flight

after landing, we stay 2 hours on the taxi way before reaching the gate The airline and the crew were good though

I'm not a fan of Southwest's model. I don't like the herding style of boarding.

My flight to Chicago left and landed early. My return flight left two minutes late and arrived 2 minutes late. My seat selections were ideal! There were no snacks going to Chicago and no snacks on the return trip. There are no charging outlets on board.

Excellent experience. WiFi worked on this leg of My trip

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)