MDW - CHS

$109 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 9/1. 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
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41,299,237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$272
Typical prices: $461-$307
Southwest
Wed 7/15Tue 7/21
MDW - CHS • Non-stop
Cheapest non-stop
$278
Typical prices: $460-$245
Southwest
Wed 9/2Sat 9/5
MDW - CHS • Non-stop
Top airlines
Southwest
Cheapest • from $272 (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 09m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
When to travel
January
Cheapest • 100% price drop
June
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Start a new search
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

Wed, Jul 15 - Tue, Jul 21
Southwest Logo
6:20 pm - 9:30 pm
MDW
-
CHS
2h 10mnonstop
Southwest Logo
6:35 am - 1:35 pm
CHS
-
MDW
8h 00m
2 stops
$272Southwest
Wed, Jul 15 - Tue, Jul 21
Delta Logo
11:05 am - 5:16 pm
MDW
-
CHS
5h 11m
1 stop
Delta Logo
7:06 am - 12:38 pm
CHS
-
MDW
6h 32m
1 stop
$277Delta
Wed, Sep 2 - Sat, Sep 5
Southwest Logo
6:00 pm - 9:10 pm
MDW
-
CHS
2h 10mnonstop
Southwest Logo
7:35 am - 8:45 am
CHS
-
MDW
2h 10mnonstop
$278Southwest
Wed, Jul 15 - Tue, Jul 21
Southwest Logo
11:25 am - 6:15 pm
MDW
-
CHS
5h 50m
1 stop
Southwest Logo
3:00 pm - 10:40 pm
CHS
-
MDW
8h 40m
2 stops
$282Southwest
Wed, Jul 15 - Tue, Jul 21
Southwest Logo
11:25 am - 8:30 pm
MDW
-
CHS
8h 05m
2 stops
Southwest Logo
10:45 am - 6:15 pm
CHS
-
MDW
8h 30m
2 stops
$287Southwest
Wed, Sep 2 - Sat, Sep 5
Southwest Logo
6:40 am - 4:20 pm
MDW
-
CHS
8h 40m
1 stop
Southwest Logo
7:35 am - 8:45 am
CHS
-
MDW
2h 10mnonstop
$288Southwest
Wed, Jul 1 - Sat, Jul 4
Southwest Logo
6:20 pm - 9:25 pm
MDW
-
CHS
2h 05mnonstop
Southwest Logo
5:30 am - 6:40 am
CHS
-
MDW
2h 10mnonstop
$289Southwest
Wed, Sep 2 - Sat, Sep 5
Southwest Logo
10:10 am - 7:45 pm
MDW
-
CHS
8h 35m
2 stops
Southwest Logo
7:35 am - 8:45 am
CHS
-
MDW
2h 10mnonstop
$293Southwest
Sat, Sep 5 - Tue, Sep 8
Delta Logo
4:39 pm - 10:01 pm
MDW
-
CHS
4h 22m
1 stop
Delta Logo
4:30 pm - 9:46 pm
CHS
-
MDW
6h 16m
1 stop
$298Delta
Wed, Jul 1 - Sat, Jul 4
Southwest Logo
6:20 pm - 9:25 pm
MDW
-
CHS
2h 05mnonstop
Southwest Logo
12:05 pm - 6:55 pm
CHS
-
MDW
7h 50m
1 stop
$299Southwest
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.

How much is a round-trip flight from Chicago Midway Airport to Charleston?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Chicago Midway Airport to Charleston departing in July.

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 Wednesday 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 $422 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 $389, prices are generally cheapest when you fly direct.

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$109
Best time to beat the crowds with an average 35% drop in price.
Most popular time to fly with an average 2% increase in price.
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 $109 for a one-way ticket and $272 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 $172 or less one-way and $377 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 4254 reviews
8.1Boarding
8.0Comfort
7.5Entertainment
7.0Food
8.6Crew
Airline reviews

Flight coming out of Buffalo was delayed, so we had to be rescheduled on another flight from Baltimore to Phoenix which means we had a long layover and got home 3.5 hours late. Shuttle to parking stopped at 10pm, so we had to pay for an Uber to the parking lot and got charged an extra day of parking since it was after midnight. Not the best experience. Long day!

2.0 MediocreDawn, Jun 2026
BUF - BWI
Read more Southwest reviews

Flight coming out of Buffalo was delayed, so we had to be rescheduled on another flight from Baltimore to Phoenix which means we had a long layover and got home 3.5 hours late. Shuttle to parking stopped at 10pm, so we had to pay for an Uber to the parking lot and got charged an extra day of parking since it was after midnight. Not the best experience. Long day!

Was fine, delayed and feels like southwest is always late

I don't know why flying out of Sarasota requires two plane changes.

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.

The flight was smooth. The Southwest experience has degraded overall, but this one was okay.

No gluten free snacks. Seats felt worn or bare bones even though it was a new 737 MAX 8.

One major problem that was very unprofessional and uncalled for. Plane landed and we had to wait 20 minutes to get off the plane since they were waiting for someone to come to the gate to drive the jetway. Southwest couldn't have someone available and waiting for the plane to land? Is there only one person in Hobby airport who knows to drive the jetway? Was he at lunch? In the bar? Uncomfortable and uncalled for!

The checking experience in Orlando was terrible, almost missed the flight. Too many travelers and Southwest completely understaffed.

I'm glad it wasn't only 75% full because I could get a good seat

if I was good. Not happy that I have to pay extra money to get the seat I need for lake room, but I guess that’s a sign of the times.

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)