CHS - MDW

$73 Find Cheap Flights from Charleston to Chicago Midway Airport

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 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 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
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$274
Overall average: $571
Southwest
Mon 5/18Tue 5/19
CHS - MDW • 1 stop
Cheapest non-stop
$276
Southwest
Wed 4/15Fri 4/17
CHS - MDW • Non-stop
Advice from real travelers
AI-powered summary based on content written by travel experts. AI can make mistakes.
Arrive at CHS 90 minutes early for full flights.
Take the CTA Orange Line from MDW to downtown Chicago.
Expert advice
Expert advice
Expert advice
Expert advice
Top airlines
Cheapest • from $274 (round-trip)
Best reviews • 8.0 score
Airline reviews
Airline reviews
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Airline reviews
Airline reviews
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Nonstop flights
You can fly direct with Southwest. Average duration is 2h 19m
Direct flights
Direct flights
+1
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Direct flights
Direct flights
+1
When to travel
Cheapest • 47% price drop
Most popular
Good to know
Good to know
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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
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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

Mon, May 18 - Tue, May 19
Southwest Logo
5:45 pm - 11:55 pm
CHS
-
MDW
7h 10m
1 stop
Southwest Logo
8:15 am - 3:00 pm
MDW
-
CHS
5h 45m
1 stop
$274Southwest
Tue, May 5 - Sat, May 9
Southwest Logo
3:40 pm - 9:50 pm
CHS
-
MDW
7h 10m
1 stop
Southwest Logo
9:10 am - 8:15 pm
MDW
-
CHS
10h 05m
2 stops
$276Southwest
Thu, Apr 16 - Sun, Apr 19
Multiple Airlines Logo
3:01 pm - 7:59 am
CHS
-
MDW
17h 58m
1 stop
Multiple Airlines Logo
9:04 am - 8:43 am
MDW
-
CHS
22h 39m
1 stop
$277Multiple Airlines
Mon, May 18 - Wed, May 20
Southwest Logo
2:15 pm - 5:50 pm
CHS
-
MDW
4h 35m
1 stop
Southwest Logo
10:15 am - 8:00 pm
MDW
-
CHS
8h 45m
2 stops
$279Southwest
Thu, Apr 9 - Mon, Apr 13
Southwest Logo
4:45 pm - 10:20 pm
CHS
-
MDW
6h 35m
1 stop
Southwest Logo
6:50 pm - 9:55 pm
MDW
-
CHS
2h 05mnonstop
$281Southwest
Fri, Apr 17 - Fri, Apr 24
Southwest Logo
5:45 pm - 11:55 pm
CHS
-
MDW
7h 10m
1 stop
Southwest Logo
11:40 am - 9:30 pm
MDW
-
CHS
8h 50m
2 stops
$282Southwest
Mon, May 4 - Fri, May 8
Multiple Airlines Logo
8:28 pm - 10:02 pm
CHS
-
MDW
26h 34m
2 stops
Multiple Airlines Logo
4:52 pm - 8:48 am
MDW
-
CHS
14h 56m
1 stop
$283Multiple Airlines
Tue, May 5 - Sat, May 9
Southwest Logo
12:00 pm - 7:30 pm
CHS
-
MDW
8h 30m
2 stops
Southwest Logo
7:45 am - 7:10 pm
MDW
-
CHS
10h 25m
2 stops
$284Southwest
Thu, Apr 9 - Mon, Apr 13
Southwest Logo
7:40 am - 8:55 am
CHS
-
MDW
2h 15mnonstop
Southwest Logo
11:40 am - 9:30 pm
MDW
-
CHS
8h 50m
2 stops
$286Southwest
Fri, Apr 17 - Fri, Apr 24
Southwest Logo
1:15 pm - 8:35 pm
CHS
-
MDW
8h 20m
2 stops
Southwest Logo
11:40 am - 9:30 pm
MDW
-
CHS
8h 50m
2 stops
$287Southwest
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.

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, Tuesday 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 October, where tickets cost $229 (return) on average. On the other hand, the most expensive months are March and May, where the average cost of round-trip tickets is $719 and $571 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.

No, with an average price for the route of $369, prices are generally cheapest when you fly direct.

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 seasonJanuary
Cheapest flight$73
Best time to beat the crowds with an average 3% drop in price.
Most popular time to fly and prices are also 31% 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 3 days, the lowest price for a flight from Charleston to Chicago Midway Airport was $73 for a one-way ticket and $274 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, Alaska Airlines, JetBlue, and Delta 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 Embraer 175 (Enhanced Winglets) 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 $381 and an overall rating of 8.0, Southwest is the most popular choice. Delta is also a great choice for the route, with an average price of $548 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 $216 or less one-way and $423 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.
8.0
SouthwestOverall score based on 4318 reviews
8.0Comfort
8.1Boarding
7.5Entertainment
7.0Food
8.6Crew
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

We landed and sat on the tarmac for 45 minutes because they only have one gate at the airport and there was another plane running late so we had to wait

The WiFi was not working. That made for a long flight.

Absolutely no communication on why there's a delay and multiple flight time reschedules. I would have canceled the flight and drove back home if I known it was going to be rescheduled 3 or 4 times.

Another late night flight and MORE men belligerently drinking and yelling. I had to move from first to economy because they were so obnoxious and disruptive. Crazy to go from a cozy chair to cardboard when you were supposed to be in first. Delta allows was too much drinking which leads to belligerent behavior.

I was in first class and literally the men behind me were so aggressively loud I moved myself to economy. This has become so common on Delta - people using audio without headphones, and men on 12am / late night flights drinking and yelling to talk to each other which prevents anyone around them from resting. Pretty crazy to have to move from first to economy (poorer service, less comfort...). Wild wild. Looking into other airlines.

Love delta smaller commuter plane so no entertainment and paid wifi on MKE-LGA leg was extremely unreliable and slow

Stop changing gates. Stop cancelling flights Stop moving my seat.

Extremely disappointed with Delta. They canceled flight last minute and then I rebooked the other flights and with which were delayed as well

Could not get my connecting flight boarding pass until four hrs before departure! Ver annoying especially since the staff could not explain why!

The flight was flying with 30% capacity. The flight my seat from preferred seating to back of the seat. Even though i can understand that this was to balance the flight weight. The flight attendance decided to do the serving near my seat and in the middle , their noices woke me up from sleep , when i realized that the service has ended and when they were going back asked for a coffee, for which they answered they have completed teh service in my location. That really upset me as they woke me up and also rejected the coffee i asked. I ended up landing with a headache, thanks to the crew that screwed up my travel

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

Information on your arrival and departure airports