CHS - MDW

$79 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 9/30. 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 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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Flights 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, Sep 8 - Mon, Sep 8
Southwest Logo
5:30 am - 6:35 amCHS-MDW
2h 05mnonstop
Southwest Logo
7:35 pm - 10:40 pmMDW-CHS
2h 05mnonstop
$157Southwest
Find Deal
Tue, Aug 26 - Wed, Sep 3
Southwest Logo
6:35 am - 7:40 amCHS-MDW
2h 05mnonstop
Southwest Logo
11:45 am - 5:00 pmMDW-CHS
4h 15m1 stop
$167Southwest
Find Deal
Tue, Aug 26 - Wed, Sep 3
Southwest Logo
6:35 am - 7:40 amCHS-MDW
2h 05mnonstop
Southwest Logo
6:25 am - 5:00 pmMDW-CHS
9h 35m2 stops
$172Southwest
Find Deal
Mon, Oct 27 - Tue, Oct 28
Southwest Logo
8:30 pm - 11:15 pmCHS-MDW
3h 45m1 stop
Southwest Logo
7:55 am - 1:15 pmMDW-CHS
4h 20m1 stop
$177Southwest
Find Deal
Sat, Nov 8 - Tue, Nov 11
Delta Logo
5:55 pm - 9:44 pmCHS-MDW
4h 49m1 stop
Delta Logo
6:00 am - 1:47 pmMDW-CHS
6h 47m1 stop
$208Delta
Find Deal
Fri, Sep 12 - Mon, Sep 15
Delta Logo
5:55 pm - 9:44 pmCHS-MDW
4h 49m1 stop
Delta Logo
1:05 pm - 8:41 pmMDW-CHS
6h 36m1 stop
$244Delta
Find Deal
Thu, Sep 18 - Sun, Sep 21
Frontier Logo
3:41 pm - 7:20 amCHS-MDW
16h 39m1 stop
Frontier Logo
8:15 am - 2:36 pmMDW-CHS
5h 21m1 stop
$311Frontier
Find Deal
Thu, Sep 11 - Sun, Sep 14
Frontier Logo
3:41 pm - 7:20 amCHS-MDW
16h 39m1 stop
Frontier Logo
8:15 am - 2:36 pmMDW-CHS
5h 21m1 stop
$312Frontier
Find Deal
Tue, Jun 24 - Fri, Jun 27
 Logo
7:03 am - 3:37 pmCHS-MDW
33h 34m2 stops
 Logo
10:34 am - 10:29 pmMDW-CHS
34h 55m2 stops
Thu, Jul 17 - Mon, Jul 21
 Logo
10:53 am - 2:04 pmCHS-MDW
28h 11m3 stops
 Logo
9:12 am - 10:23 pmMDW-CHS
36h 11m2 stops
Expert advice

Expert advice for your flight from Charleston to Midway

 
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
CHS

Arrive at CHS 90 minutes early. Security lines are usually short, but flights are often full, so missing one could mean days of waiting.

Read more about CHSby Brandon Schultz
MDW

Take the CTA Orange Line from MDW to downtown Chicago. It's a quick 25-30 minute ride, avoiding traffic delays.

Read more about MDWby Stefanie Waldek
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
Useful Info

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 Fridays 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 Sunday is the most expensive.

Good to know

Low seasonJuly
High seasonSeptember
Cheapest flight$79
Best time to beat the crowds with an average 15% drop in price.
Most popular time to fly and prices are also 14% 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 $79 for a one-way ticket and $157 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, and JetBlue 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 MAX 8 is the aircraft model that flies most regularly on the Charleston to Chicago Midway Airport flight route.

  • 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 $410 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 $432 and an overall rating of 8.0.

  • 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 $258 or less one-way and $310 or less round-trip.

Prefer to fly direct from Charleston to Chicago Midway Airport?

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
See more direct flights

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 4287 reviews
7.1Food
8.0Comfort
7.6Entertainment
8.2Boarding
8.6Crew
Airline reviews

Southwest is typically delayed, and it gets wearisome. It is no longer a discount airline and you get way less than you pay for when it comes to comfort and Ce.

6.0 GoodDavid, Jun 2025BWI - COS
Read more Southwest reviews

Southwest is typically delayed, and it gets wearisome. It is no longer a discount airline and you get way less than you pay for when it comes to comfort and Ce.

We sat on the plane on the tarmac for 4 hours.

I'm not a fan of Southwest's model. I don't like the herding style of boarding.

Flight crew and cabin crew were great. I had to rearrange flights because my original flight was 3hrs delayed for weather, the rub is the flight I moved to boarded on time then we sat at the gate for 2 hours because scheduling stole our first officer for another flight, TWICE. Then our actual FO was an hour delayed. To make it worse my original flight went from a 3 hour delay to departing 15min EARLY. Just poor scheduling operations all around.

Bring back peanuts Take our drink orders when were all seated, especially after you switch to assigned seating.

Staff was far less than helpful at all times. Departure and arrival times mean nothing to Southwest. Extremely disappointed, will never fly with them again, and I’ll be sure to share my experience with all.

It is southwest seat was ok. Not the most comfortable seat

I’ve always loved Southwest. No issues at all. I was flying standby and the gate agent was extremely friendly and helpful. Boarding was smooth and I was able to get a window seat in the emergency exit row. Crew was fantastic! They were very professional and accommodating. We had to divert from our destination due to weather but the flight crew kept everyone at ease and informed us of all pertinent information. Excellent flight

The price of the tickets isn't matching the flight experience. No matter how long the flight is, you're only getting pretzels. The flight attendants looked unkept and over it.

Plz don't take away free bags and free seating

Great service. Flight was delayed while we sat on the runway for a couple of hours. Weather related. Staff made is very bearable. The steward servicing the first class cabin was exceptional. Thank you! 💗

5 hours of delay that could've been much shorter if Delta had taken the 1 hour delay they imposed on the flight before boarding to run any of the plane checks required for flight to find the hydraulic issue that required nearly 3 hours to fix. $24 of meal credit buys a sandwich and a soft drink. Poor communication within the terminal about what gate we'd be re-boarding from and when we'd be re-boarding.

Amazing flight! I have never noticed the uniforms of the attendants before in twenty years of flying except today when one female had the most amazing dress on. It was beautifully designed and showed she was in charge. I never dreamed I would google who designed Delta uniforms . The ultimate compliment is when another woman admires your outfit. . I hope your designer puts it on the market

It would be nice if was given wires ear buds. Overall was a good experience was able to sleep on the plane

My flight was 6 pm 6/6. Every hour they delayed it again - air condition issues then no pilot then the crew had worked too many hours and cancelled the flight at 11 pm. Sent customers to NJ a 45 minutes uber ride to a hotel. Had to be back by 5 am for a 7 am flight and again no pilot etc with another three hours of delays.

The entertainment and wifi mostly didn't work on this flight.

Terrible entertainment system - kept freezing and audio kept cutting out. Snacks were mediocre at best for a 5 hour flight.

The check in and bag drop off for Sky Priority members is slow. The Clear security was also slow - a TSA issue.

I am still upset that my bag was lost on a recent trip to Rome ; we were inconvenienced and out €150 Euros ; delta has refused to reimburse us

I am very bothered by the events today. I can't believe the flight attendants allowed someone to take my seat and made me move. It was embarrassing. I was in the right. The lady just didn't want move. I can't believe delta would allow this to stand and disrespect my rights as a passenger. The lady complained about her leg and that she couldn't move. Firstly somehow she was able to make it to row 24. Not sure how much her leg could have hurt. Secondly, I'm in plenty of pain myself. I just finished chemotherapy a several weeks ago. My body is constantly sore. Yet deltas flight attendants didn't appropriately protect my rights. In the end they found me a seat on the plane but I want to understand how delta can operate this way. They in essence allowed a bully to get their way.

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

Information on your arrival and departure airports

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