MDW - CHS

$102 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 10/20. 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

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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Booking Insights
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

Sun, Oct 5 - Sat, Oct 11
Multiple Airlines Logo
6:21 am - 2:28 pmMDW-CHS
7h 07m1 stop
Multiple Airlines Logo
8:10 pm - 11:44 amCHS-MDW
16h 34m1 stop
$257Multiple Airlines
Find Deal
Thu, Oct 16 - Mon, Oct 20
Multiple Airlines Logo
11:49 am - 8:57 amMDW-CHS
20h 08m1 stop
Multiple Airlines Logo
9:10 pm - 1:38 pmCHS-MDW
17h 28m2 stops
$260Multiple Airlines
Find Deal
Tue, Sep 30 - Fri, Oct 3
Multiple Airlines Logo
2:32 pm - 2:29 pmMDW-CHS
22h 57m2 stops
Multiple Airlines Logo
3:33 pm - 10:21 amCHS-MDW
19h 48m1 stop
$268Multiple Airlines
Find Deal
Tue, Oct 21 - Wed, Oct 29
Southwest Logo
1:25 pm - 4:25 pmMDW-CHS
2h 00mnonstop
Southwest Logo
5:35 am - 6:45 amCHS-MDW
2h 10mnonstop
$293Southwest
Find Deal
Tue, Oct 21 - Wed, Oct 29
Southwest Logo
1:25 pm - 4:25 pmMDW-CHS
2h 00mnonstop
Southwest Logo
3:25 pm - 6:30 pmCHS-MDW
4h 05m1 stop
$299Southwest
Find Deal
Sat, Oct 18 - Mon, Oct 20
Southwest Logo
9:45 am - 12:45 pmMDW-CHS
2h 00mnonstop
Southwest Logo
8:30 pm - 11:15 pmCHS-MDW
3h 45m1 stop
$303Southwest
Find Deal
Thu, Jan 1 - Wed, Jan 7
Delta Logo
9:54 am - 3:09 pmMDW-CHS
4h 15m1 stop
Delta Logo
12:15 pm - 4:25 pmCHS-MDW
5h 10m1 stop
$306Delta
Find Deal
Thu, Dec 4 - Sat, Dec 6
Southwest Logo
2:10 pm - 9:15 pmMDW-CHS
6h 05m2 stops
Southwest Logo
6:10 am - 7:25 amCHS-MDW
2h 15mnonstop
$308Southwest
Find Deal
Tue, Nov 11 - Tue, Nov 18
Delta Logo
10:35 am - 3:17 pmMDW-CHS
3h 42m1 stop
Delta Logo
6:30 am - 9:51 amCHS-MDW
4h 21m1 stop
$313Delta
Find Deal
Thu, Jan 8 - Sun, Jan 18
Delta Logo
6:00 am - 11:25 amMDW-CHS
4h 25m1 stop
Delta Logo
6:30 am - 9:56 amCHS-MDW
4h 26m1 stop
$331Delta
Find Deal

Everything you should know

Our travelers' advice
AI-generated summary based on content written by travel experts
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 $293 (round-trip)
Southwest
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
When to travel
May
Cheapest • 15% price drop
March
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Cheapest round-trip
$257
Overall average: $345
Multiple Airlines
Sun 10/5Sat 10/11
MDW - CHS • 1 stop
Cheapest non-stop
$293
Typical prices: $384-611
Southwest
Tue 10/21Wed 10/29
MDW - CHS • Non-stop
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!
Expert advice

Expert advice for your flight from Midway to Charleston

 
Snippets provided in this section are AI-generated based on a summarization of KAYAK-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Airports
MDW

Midway offers a compact and easy-to-navigate terminal with a variety of dining and shopping options, making it convenient for travelers.

Read more about MDWby Stefanie Waldek
CHS

For a quick and cost-effective ride to downtown Charleston, consider using rideshare services like Uber or Lyft from CHS.

Read more about CHSby Brandon Schultz
Our travel experts
Stefanie Waldek

Stefanie Waldek

Expert on MDW

Stefanie Waldek

Stefanie Waldek

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

Brandon Schultz

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
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 May, where tickets cost $302 (return) on average. On the other hand, the most expensive months are September and February, where the average cost of round-trip tickets is $460 and $448 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.

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 $290 on average.

Good to know

Low seasonJanuary
Cheapest flight$102
Best time to beat the crowds with an average 0% drop in price.
Most popular time to fly and prices are also 4% 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 $102 for a one-way ticket and $257 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 $184 or less one-way and $445 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 4242 reviews
7.0Food
7.5Entertainment
8.0Comfort
8.6Crew
8.1Boarding
Airline reviews

I wish they had movie screens in the headrests. The seats are much improved, more legroom and recently renovated. Bathroom was clean. Staff was outstanding!!

10.0 ExcellentG, Sep 2025LAS - ATL
Read more Southwest reviews

I wish they had movie screens in the headrests. The seats are much improved, more legroom and recently renovated. Bathroom was clean. Staff was outstanding!!

As always, the entire Southwest experience was wonderful, from online booking to flight to baggage retrieval. Very grateful.

The weather could have been better. There was a 40 minute ATC delay in SFO because of marine fog and a micro cell storm delayed landing and take-off at Nashville. The gate was changed 5 minutes from boarding from gate B3 to gate C23 at Nashville airport.

After being assaulted by a flight attendant I was then brushed off as oh well because he long braids didn’t mean to whip me in the eye. I have filed complaints and will see. But like any other issue I’ve had with kayak involved it’s been trash. Last time I’ll be using your app

AC sub par. WiFi not working correctly. Ac sucked. Seats very narrow.

Near 4 hour flight with only 1 service. Had to use call button to request water. Internet and power not working until into flight. Internet would stop working during flight.

Southwest's seats are the least comfortable I have ever sat in.

The cabin was quiet for the redeye flight. The area was clean. The staff was great. The 787 Max was in good condition. Drawbacks were that the seat widths were tight for some passengers. The seat padding was at best average and for a long flight uncomfortable.

Southwest like most American domestic airlines, is a mediocre airline. But it is among the cheapest. Oh well.

My flight was delayed 50 minutes and we were rushed to board to then sit for 15 minutes until the pilot arrived. Unacceptable since we could have waited to board. Also the delayed flight was updated AFTER we boarded to more than the 10 minutes as originally stated.

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

Information on your arrival and departure airports

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