CHS - MDW

$113 Find Cheap Flights from Charleston to Chicago Midway Airport - 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 Charleston to Midway departing on 8/4. 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 Chicago Midway Airport

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Charleston to Chicago, 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 Charleston to Chicago, as well as popular online travel agencies
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Everything you should know

Cheapest round-trip
$277
Typical prices: $295-$246
Delta
Sat 7/11Wed 7/15
CHS - MDW • 1 stop
Cheapest non-stop
$279
Southwest
Tue 7/14Wed 7/15
CHS - MDW • Non-stop
Top airlines
Cheapest • from $277 (round-trip)
Best reviews • 7.9 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
You can fly direct with Southwest. Average duration is 2h 13m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
When to travel
Cheapest • 100% price drop
Most popular
Good to know
Good to know
+1
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Good to know
Good to know
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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 Midway!
Flight Deals
Booking Insights
Expert advice
Flight Deals

Cheap Flights from Charleston to Midway (CHS-MDW)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Charleston to Midway 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 Charleston to Midway

Sat, Jul 11 - Wed, Jul 15
Delta Logo
6:24 pm - 10:15 pm
CHS
-
MDW
4h 51m
1 stop
Delta Logo
6:00 am - 12:00 pm
MDW
-
CHS
5h 00m
1 stop
$277Delta
Wed, Jul 8 - Tue, Jul 14
Delta Logo
6:28 pm - 10:15 pm
CHS
-
MDW
4h 47m
1 stop
Delta Logo
12:41 pm - 8:49 pm
MDW
-
CHS
7h 08m
1 stop
$278Delta
Thu, Aug 6 - Mon, Aug 10
Southwest Logo
4:05 pm - 11:45 pm
CHS
-
MDW
8h 40m
1 stop
Southwest Logo
6:15 pm - 9:25 pm
MDW
-
CHS
2h 10mnonstop
$279Southwest
Sat, Jul 25 - Wed, Jul 29
Southwest Logo
1:30 pm - 7:25 pm
CHS
-
MDW
6h 55m
1 stop
Southwest Logo
8:20 am - 4:10 pm
MDW
-
CHS
6h 50m
2 stops
$282Southwest
Thu, Aug 20 - Tue, Aug 25
Southwest Logo
11:30 am - 7:30 pm
CHS
-
MDW
9h 00m
2 stops
Southwest Logo
10:30 am - 6:20 pm
MDW
-
CHS
6h 50m
2 stops
$283Southwest
Thu, Aug 6 - Mon, Aug 10
Southwest Logo
6:30 pm - 7:40 pm
CHS
-
MDW
2h 10mnonstop
Southwest Logo
11:00 am - 4:40 pm
MDW
-
CHS
4h 40m
1 stop
$284Southwest
Sat, Oct 10 - Wed, Oct 14
Southwest Logo
6:40 am - 1:10 pm
CHS
-
MDW
7h 30m
2 stops
Southwest Logo
12:55 pm - 9:50 pm
MDW
-
CHS
7h 55m
1 stop
$288Southwest
Thu, Aug 6 - Mon, Aug 10
Delta Logo
12:59 pm - 6:33 pm
CHS
-
MDW
6h 34m
1 stop
Delta Logo
6:05 am - 1:11 pm
MDW
-
CHS
6h 06m
1 stop
$289Delta
Fri, Aug 7 - Mon, Aug 10
Delta Logo
12:59 pm - 6:33 pm
CHS
-
MDW
6h 34m
1 stop
Delta Logo
6:05 am - 1:11 pm
MDW
-
CHS
6h 06m
1 stop
$290Delta
Thu, Aug 6 - Tue, Aug 11
Southwest Logo
4:05 pm - 11:45 pm
CHS
-
MDW
8h 40m
1 stop
Southwest Logo
11:10 am - 7:45 pm
MDW
-
CHS
7h 35m
2 stops
$294Southwest
Booking Insights

KAYAK's insights & trends for Charleston to Midway flights

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

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

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

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

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

If you are looking for a flight deal from Charleston to Chicago Midway Airport, look for departures on Wednesdays and avoid leaving on a Sunday, as it's usually the priciest day. When flying back from Chicago Midway Airport, Wednesday is the cheapest day to fly and Thursday is the most expensive.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Charleston to Chicago Midway Airport, 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 Charleston to Chicago Midway Airport is March, where tickets cost $0 (return) on average. On the other hand, the most expensive months are December and February, where the average cost of round-trip tickets is $548 and $529 respectively.

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

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 $321 on average.

Expert advice

Expert advice for your flight from Charleston to Midway

 
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.

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.

Good to know

Low seasonOctober
Cheapest flight$113
Best time to beat the crowds with an average 50% drop in price.
Most popular time to fly and prices are also 20% lower on average.
Flight from Charleston to Chicago Midway Airport

When to book flights from Charleston to Midway

Are your dates flexible? Find out the best times to travel from Charleston to Midway 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 Charleston to Chicago Midway Airport flights

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

    In the last 5 days, the lowest price for a flight from Charleston to Chicago Midway Airport was $113 for a one-way ticket and $277 for a round-trip.

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

    Even though you are not required to have a passport, keep in mind that an official ID is needed to board the airplane.

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

    American Airlines, Delta, JetBlue, and Alaska Airlines offer inflight Wi-Fi service on the Charleston to Chicago Midway Airport flight route.

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

    The Boeing 737-800 is the aircraft model that flies most regularly on the Charleston to Chicago Midway Airport flight route.

  • Which airline alliances offer flights from Charleston to Chicago Midway Airport?

    SkyTeam is the only airline alliance operating flights between Charleston and Chicago Midway Airport.

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

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

  • Which is the best airline for flights from Charleston to Chicago, Southwest or Delta?

    The two airlines most popular with KAYAK users for flights from Charleston to Chicago are Southwest and Delta. With an average price for the route of $302 and an overall rating of 7.9, Southwest is the most popular choice. Delta is also a great choice for the route, with an average price of $478 and an overall rating of 7.9.

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

    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 Charleston to Chicago Midway Airport.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago Midway Airport from Charleston 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 Charleston to Chicago Midway Airport?

    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 Chicago Midway Airport with an airline and back to Charleston with another airline. Booking your flights between Charleston and MDW 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 Charleston to Chicago Midway Airport?

    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 Chicago Midway Airport from Charleston 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 Charleston to Chicago Midway Airport

  • Looking for a cheap flight? 25% of our users found flights on this route for $180 or less one-way and $361 or less round-trip.

Prefer to fly direct from Charleston to Chicago Midway Airport?

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

Direct departures

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

Direct returns

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

Reviews of the top airlines flying from Charleston to Midway

 
See real verified KAYAK customer reviews for airlines flying from Charleston to Chicago. 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 Charleston to Midway? 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 4235 reviews
8.6Crew
7.5Entertainment
7.0Food
8.1Boarding
8.0Comfort
Airline reviews

Flight was delayed over 3 hours. Planes were dirty. Staff indifferent. And they serve vegan pretzels as snacks.

2.0 MediocreMatthew, Jun 2026
CVG - MDW
Read more Southwest reviews

Flight was delayed over 3 hours. Planes were dirty. Staff indifferent. And they serve vegan pretzels as snacks.

It was great. The gate staff were very helpful in Portland when my son forgot his rolling bag and had to go back to get it just in time to make it on the plane. We really appreciate that. Great job!

Airline is not very senior friendly. Flights are late, forcing us to run to the connecting flight. Food is awful. Wish they would go back to pretzels and peanuts. During flight, pressurization isn’t quite right and all of our ears get plugged. Everything is nickel and dime, charging for boarding, seat selection and legroom. While a screen at the desk in the gate area says check your roll on bag now for free due to space limitation, the employee at the desk will not check the bag without a $100 fee. Insane.

Kayak could’ve posted the correct gate number. Almost missed my flight.

Slow boarding, limited food and drink portions. Bad delays and turbulence

there were two flight attendants that were up front...that were the best! They get KUDOs for making my trip only fantastic. Tell them Jeff said that!

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.

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.

I have Precheck. Flew HPN to DEN and return this past weekend. Delta didn't attach my Precheck number to this trip. So it was waiting in general line especially in Denver. Unavailable.

Original flight was delayed, then cancelled and the gate staff did not expedite rebooking. Also, no instructions were given that a ticket number was needed before being called to facilitate rebooking. This could have been much more organized.

Be on time? When not on time a circling for over an hour offer more than 1 bag of chips to the passengers? It was a 7 hour flight by the time we got done.

Five hour delays every hour, I wish it were all at once

Flight delayed four separate times. I’m now one hour hours late to landing.

worst flight ever from Delta, it got delayed and kept on delaying..

Should never have had to go to Detroit from Orlando back to Tennessee!

Got rerouted from a straight flight from Orlando to Atlanta to Knoxville to a flight from Orlando to Detroit to Knoxville! Seriously!! Flight delay out of Detroit! Long day for what should have been a pretty easy travel day!

Two delays on two separate planes with parts they could not easily find and replace.

Checkin was good, fllight ws good. Onlly complaint is lack of foot on 6 hour flight from Seattle to Boston. Snacks were flimsy - chips and cookies. could have offered something more substantial for such a long flight. I know you can buy food in airport but for the price you pay for a ticket, they should step up for the passengers.

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

Information on your arrival and departure airports