CHS - MDW

$69 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 3/18. 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
$179
Typical prices: $320-$626
Multiple Airlines
Tue 5/5Sat 5/9
CHS - MDW • 1 stop
Cheapest non-stop
$279
Southwest
Sat 2/21Mon 2/23
CHS - MDW • Non-stop
Our travelers' advice
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
Southwest
Cheapest • from $279 (round-trip)
Southwest
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
When to travel
October
Cheapest • 44% price drop
September
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 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

Tue, May 5 - Sat, May 9
Multiple Airlines Logo
3:35 pm - 1:00 pm
CHS
-
MDW
22h 25m
1 stop
Multiple Airlines Logo
7:30 am - 2:40 pm
MDW
-
CHS
6h 10m
1 stop
$179Multiple Airlines
Tue, May 5 - Sat, May 9
Multiple Airlines Logo
3:35 pm - 1:00 pm
CHS
-
MDW
22h 25m
1 stop
Multiple Airlines Logo
7:30 am - 2:40 pm
MDW
-
CHS
6h 10m
1 stop
$181Multiple Airlines
Mon, May 4 - Fri, May 8
Multiple Airlines Logo
3:35 pm - 1:00 pm
CHS
-
MDW
22h 25m
1 stop
Multiple Airlines Logo
7:30 am - 2:40 pm
MDW
-
CHS
6h 10m
1 stop
$188Multiple Airlines
Mon, May 4 - Fri, May 8
Multiple Airlines Logo
3:35 pm - 1:00 pm
CHS
-
MDW
22h 25m
1 stop
Multiple Airlines Logo
7:30 am - 2:40 pm
MDW
-
CHS
6h 10m
1 stop
$191Multiple Airlines
Sun, Feb 8 - Mon, Feb 9
Multiple Airlines Logo
5:05 pm - 11:45 am
CHS
-
MDW
19h 40m
2 stops
Multiple Airlines Logo
7:00 pm - 8:38 am
MDW
-
CHS
12h 38m
1 stop
$230Multiple Airlines
Sat, Feb 7 - Mon, Feb 9
Multiple Airlines Logo
6:35 pm - 11:45 am
CHS
-
MDW
18h 10m
2 stops
Multiple Airlines Logo
7:00 pm - 8:38 am
MDW
-
CHS
12h 38m
1 stop
$232Multiple Airlines
Tue, Apr 14 - Thu, Apr 16
Multiple Airlines Logo
5:02 pm - 1:00 pm
CHS
-
MDW
20h 58m
1 stop
Multiple Airlines Logo
7:30 am - 2:40 pm
MDW
-
CHS
6h 10m
1 stop
$255Multiple Airlines
Mon, Mar 23 - Thu, Mar 26
Multiple Airlines Logo
5:02 pm - 1:02 pm
CHS
-
MDW
21h 00m
1 stop
Multiple Airlines Logo
7:30 am - 4:00 pm
MDW
-
CHS
7h 30m
1 stop
$273Multiple Airlines
Sat, Feb 21 - Mon, Feb 23
Southwest Logo
6:00 am - 7:15 am
CHS
-
MDW
2h 15mnonstop
Southwest Logo
2:45 pm - 5:45 pm
MDW
-
CHS
2h 00mnonstop
$279Southwest
Mon, May 4 - Fri, May 8
Multiple Airlines Logo
3:35 pm - 1:00 pm
CHS
-
MDW
22h 25m
1 stop
Multiple Airlines Logo
4:09 pm - 8:48 am
MDW
-
CHS
15h 39m
2 stops
$283Multiple Airlines
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 May.

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, Monday 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 April and December, where the average cost of round-trip tickets is $587 and $548 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$69
Best time to beat the crowds but there is an average 4% increase in price.
Most popular time to fly and prices are also 13% 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 $69 for a one-way ticket and $179 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 Embraer 175 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?

    You can catch a nonstop flight from Charleston to Chicago Midway Airport on Monday, Tuesday, Thursday, Friday, Saturday, and Sunday.

  • 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 $364 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 $628 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 $185 or less one-way and $339 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 4268 reviews
8.6Crew
7.0Food
8.1Boarding
7.5Entertainment
8.0Comfort
Airline reviews

All good except once again bags took an hour at Midway Airport Happens all the time. Ridiculous

10.0 ExcellentAnonymous, Jan 2026
PHX - MDW
Read more Southwest reviews

All good except once again bags took an hour at Midway Airport Happens all the time. Ridiculous

Everything went smoothly and we even arrived a little bit early.

Great vacation. Can't wait till next year for another one.

Great flight but super high price. Glad it was a business trip and not personal

On time. Friendly staff. Took to long to pre bord all the specialty groups. Cramped small plane

The seats were comfortable, and the boarding process was pretty smooth.

3 hour delay. Had to change plans and was still delayed.

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

The crew canceled the complementary snack and drink in anticipation of turbulence that never materialized. I was counting on the drink (water) to take the the doses of medication - prescribed for my heart condition - that were due during the flight. Since no snack or meal was served on this flight, I cannot rate the food quality. Otherwise, this flight was excellent.

Departure was delayed more than 1/2 hour while we waited for luggage (only) transfer from another flight/plane. Once approved for takeoff, the flight was excellent.

The service from the flight attendants were of supreme quality. They greeted and treated everyone with a wide smile. This is totally absent nowadays. Kudos to them!!!!

Excellent flight and got us around tough weather. Only issue was seat TV did not work and crew tried to reboot.

Very large passenger too space from my own seat. Arm board couldn’t be lowered because of his size. It wads very uncomfortable trip, as the flight was full couldn’t move anywhere having back pain because of the position in which I was the entire flight.

was sitting in the jet bridge for 10 minutes in -20 degree weather waiting for my bag

Outdated equipment in disrepair, wifi inoperable. Broken seats, taped air vents, generally poor condition, the 717 showed its age and lack of upkeep.

My flight out of Baton Rouge to Atlanta was delayed by a half hour. This got us into Atlanta airport 30 minutes late. I ran through the airport to get to my connecting flight. As I approached the boarding gate, I saw the boarding door was still open and a passenger was being checked in. But when I got to the gate, the boarding agent told me they had already given away my seat and there were no empty seats on that flight. So I had to take a later flight. That has never happened to me before. Very frustrating.

Connection through Atlanta was difficult. Mechanical issue on plane caused a two hour delay. New gate was a mile away.

No WiFi. Comfort plus should have alcohol provided, crew only offered water or tea. Who the heck wants tea?

The flight was delayed and oversold. I volunteered to give up my seat for compensation. Thinking I could get a good night's sleep instead of arriving home at 2 am. It took over an hour to get the new reservation confirmed, three different gate attendants, and two red coats. It took even longer to confirm the overnight hotel, and when I arrived, the line was 45 minutes long, with two people checking in, and at least 15 people slowly, very slowly—no food except frozen convenience food, no coupon for food from airlines. Slept, headed back to the airport, and that flight had an equipment change and a gate change just as they were about to board. It took an additional hour to board as they cleaned the plane from storage.

There was no wifi available on this flight. And there were no screens, no onboard entertainment, no entertainment options at all. It was like travelling in the 1990s again, except without even a main screen for options. Seats, as usual, were tight and uncomfortable.

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

Information on your arrival and departure airports