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Cheap flights from Chicago Midway to Charleston

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Compare Chicago Midway to Charleston flight deals

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Flight deals from Chicago Midway to Charleston

Looking for a cheap last-minute deal or the best round-trip flight from Chicago Midway to Charleston? Find the lowest prices on one-way and round-trip tickets right here.
Charleston.C$234 per passenger.Departing Sat, Jul 19, returning Tue, Jul 22.Round-trip flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departing from Chicago Midway on Sat, Jul 19, arriving in Charleston.Inbound direct flight with Southwest Airlines departing from Charleston on Tue, Jul 22, arriving in Chicago Midway.Price includes taxes and charges.From C$234, select.
Charleston.C$247 per passenger.Departing Wed, Jun 18, returning Tue, Jun 24.Round-trip flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departing from Chicago Midway on Wed, Jun 18, arriving in Charleston.Inbound indirect flight with Southwest Airlines, departing from Charleston on Tue, Jun 24, arriving in Chicago Midway.Price includes taxes and charges.From C$247, select.
Charleston.C$262 per passenger.Departing Fri, Jun 6, returning Tue, Jun 10.Round-trip flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departing from Chicago Midway on Fri, Jun 6, arriving in Charleston.Inbound direct flight with Southwest Airlines departing from Charleston on Tue, Jun 10, arriving in Chicago Midway.Price includes taxes and charges.From C$262, select.
Charleston.C$271 per passenger.Departing Thu, Jun 26, returning Wed, Jul 2.Round-trip flight with Delta.Outbound indirect flight with Delta, departing from Chicago Midway on Thu, Jun 26, arriving in Charleston.Inbound indirect flight with Delta, departing from Charleston on Wed, Jul 2, arriving in Chicago Midway.Price includes taxes and charges.From C$271, select.
Charleston.C$271 per passenger.Departing Thu, Jul 31, returning Sun, Aug 3.Round-trip flight with Delta.Outbound indirect flight with Delta, departing from Chicago Midway on Thu, Jul 31, arriving in Charleston.Inbound indirect flight with Delta, departing from Charleston on Sun, Aug 3, arriving in Chicago Midway.Price includes taxes and charges.From C$271, select.
Charleston.C$271 per passenger.Departing Fri, May 30, returning Fri, Jun 6.Round-trip flight with Delta.Outbound indirect flight with Delta, departing from Chicago Midway on Fri, May 30, arriving in Charleston.Inbound indirect flight with Delta, departing from Charleston on Fri, Jun 6, arriving in Chicago Midway.Price includes taxes and charges.From C$271, select.
Charleston.C$271 per passenger.Departing Thu, Sep 4, returning Mon, Sep 8.Round-trip flight with Delta.Outbound indirect flight with Delta, departing from Chicago Midway on Thu, Sep 4, arriving in Charleston.Inbound indirect flight with Delta, departing from Charleston on Mon, Sep 8, arriving in Chicago Midway.Price includes taxes and charges.From C$271, select.
Charleston.C$271 per passenger.Departing Thu, Aug 7, returning Sun, Aug 10.Round-trip flight with Delta.Outbound indirect flight with Delta, departing from Chicago Midway on Thu, Aug 7, arriving in Charleston.Inbound indirect flight with Delta, departing from Charleston on Sun, Aug 10, arriving in Chicago Midway.Price includes taxes and charges.From C$271, select.

Find the cheapest month to fly from Chicago Midway to Charleston

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Chicago Midway to Charleston flights are currently cheapest in July.
May
from C$332
Jun
from C$247
Jul
from C$234
Aug
from C$271
Sep
from C$271
Oct
from C$403
Nov
from C$438
Dec
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Jan
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Feb
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Mar
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Apr
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Direct flights from Chicago Midway to Charleston

Chicago Midway to Charleston: Alternative routes

Compare routes from Chicago Midway to Charleston below. You may find an airport to fly into that's cheaper, faster, or easier than Charleston.

Chicago to Charleston: Flight information

The things to know before you go.
Cheapest flight foundC$234
Cheapest month to flyJuly
Average flight time2 hrs, 5 mins
Most popular airlineSouthwest Airlines
Average flights per week8

Finding cheap flights from Chicago Midway to Charleston: Frequently asked questions

The best price we found for a round-trip flight from Chicago Midway to Charleston is C$234. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.
2 hours and 5 minutes is the average flight time from Chicago Midway to Charleston.
Southwest Airlines flies direct from Chicago Midway to Charleston.
There are 8 flights per week flying from Chicago Midway to Charleston, as of May 2025.
The cheapest month to fly from Chicago Midway to Charleston is usually May 2025.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Chicago Midway Airport to Charleston Airport on Saturday, July 19, 2025.
Yes – the average flight time is 2 hours and 5 minutes.
We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to Charleston but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.
We crunched all the numbers in our flight calendar, and it looks like the cheapest time to book a flight to Charleston is around 40 days in advance, so don’t leave your flight to the last minute.
Currently, Southwest Airlines offers the cheapest flight tickets to Charleston.

Travelling from Chicago Midway International Airport (MDW) to Charleston International Airport (CHS): what you need to know

  • Around 2 hours is how long you'll be travelling on a direct flight from Chicago Midway International Airport to Charleston International Airport.

  • Charleston's timezone is UTC-4, making Charleston one hour ahead of Chicago.

  • You can choose from five weekly Chicago Midway International Airport to Charleston International Airport flights. The 08:30 departure with Southwest Airlines is the earliest flight available. Southwest Airlines operates the latest service of the day at 21:15.

  • To ensure you catch your MDW to CHS flight, leave enough time to check in and drop off your luggage. Arriving two hours before international departures and an hour before domestic flights is the standard rule.

  • During popular months like July, it's a good idea to get to the airport even earlier. Arrive two hours before a domestic departure and four hours ahead of an international flight whenever you're travelling during a high season in general.

  • Southwest Airlines offers direct flights from Chicago Midway International Airport to Charleston International Airport. Book with this popular airline, then get ready to discover the sights in Charleston — and maybe even more of United States if your schedule allows.

  • The majority of passengers choose to fly with Southwest Airlines on this route.

  • Southwest Airlines is the most punctual carrier operating MDW to CHS flights. A dependable 88.24% of its services on this route arrive without delay.

  • Think about adding a stopover when booking your ticket from Chicago Midway International Airport to Charleston International Airport. Simply deselect 'Direct flights only' to break up your journey, or maybe even explore a new city along the way. Here's where you can stop between MDW and CHS:

    • Nashville International Airport

    • Hartsfield-Jackson Atlanta International Airport

    • Detroit Metropolitan Wayne County Airport

How to find the cheapest flights from Chicago Midway International Airport (MDW) to Charleston International Airport (CHS)

  • The lowest price we've seen for a one-way Chicago Midway International Airport to Charleston International Airport flight is C$106. A round-trip ticket right now is C$234. Depending on the availability when you book, these fares may change.

  • To score cheap tickets from MDW to CHS, book your trip six months ahead of your planned departure.

  • The cheapest month for flights from Chicago Midway International Airport to Charleston International Airport is May. Use the 'Whole month' tool to see the lowest airfares if you have a flexible travel schedule.

  • Cut down on the time spent looking for cheap flights from MDW to CHS by setting up a Price Alert. You'll receive an email or push notification on the app when a lower fare becomes available.

  • Tailor your trip with filters. Select your ideal departure and arrival times, airlines and total journey duration. You can also sort the results by 'Best,' 'Cheapest' or 'Fastest' flights from Chicago Midway International Airport to Charleston International Airport.

Handy information about Chicago Midway International Airport (MDW)

  • You'll find MDW at 5700 South Cicero.

  • Of the flights that depart from Chicago Midway International Airport, 77.88% land on schedule at their destination.

  • To reach Chicago Midway International Airport from central Chicago, it takes around 20 minutes by car. Of course, this depends on traffic conditions. It's approximately 19 kilometres from the airport to the city centre.

  • Catching public transport? You can expect a journey time of around 45 minutes.

  • Get your break off to a hassle-free start by staying near MDW. Whether you have an early flight from Chicago Midway International Airport to Charleston International Airport or just don't like being rushed, these stays have you covered:

Arriving at Charleston International Airport (CHS)

Getting from Charleston International Airport (CHS) to central Charleston

  • Charleston International Airport to central Charleston has a drive time of about 30 minutes. It's approximately 21 kilometres away.

  • Travelling to the centre by public transport takes roughly 3 hours 35 minutes.

When to fly to Charleston International Airport (CHS)

  • July is the most popular month for flights from Chicago Midway International Airport to Charleston International Airport. To avoid the crowds, visit Charleston in April.

  • The warmest month in Charleston is July, with the temperature ranging between 24ºC (75ºF) and 32ºC (90ºF). Book your flights from Chicago Midway International Airport to Charleston International Airport in this month if this is the type of weather you like.

  • January has average temperatures of between 4ºC (39ºF) and 17ºC (63ºF). Look for cheap tickets from MDW to CHS sometime then if you like travelling in cooler conditions.

Explore more of United States

  • Charleston has plenty to offer, but there are so many other parts of United States you'll want to see. About 322 kilometres south-west of Charleston, a visit to Jacksonville will keep you on the go. Start with leading attractions like Jacksonville Zoo and Gardens, The Cummer Museum of Art & Gardens and Friendship Fountain.

  • Charlotte is another well-known destination in United States and is around 290 kilometres north of Charleston. No journey is complete without a visit to NASCAR Hall of Fame, Freedom Park and Carolinas Aviation Museum.

Plan the rest of your trip from Chicago to Charleston

Prices shown on this page are estimated lowest prices only. Found in the last 45 days.