Cheap Flights from Charleston to Chicago Midway

Compare Charleston to Chicago Midway flight deals

Find the cheapest month or even day of the year to fly to Chicago Midway

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Flight deals from Charleston to Chicago Midway

Looking for a cheap last-minute deal or the best return flight from Charleston Airport to Chicago Midway Airport? If you want to travel next month, return fares start from R 3,843. Find the lowest prices on one-way and return tickets right here.

Find the cheapest month to fly from Charleston to Chicago Midway

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Charleston to Chicago Midway flights are currently cheapest in August.

Direct flights from Charleston to Chicago Midway

Charleston to Chicago Midway: Alternative routes

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

Charleston to Chicago: Flight information

The things to know before you go.
Cheapest flight foundR 1,920
Cheapest month to flyAugust
Average flight time2 hrs, 13 mins
Most popular airlineSouthwest Airlines
Average flights per week7

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

The best price we found for a return flight from Charleston to Chicago Midway is R 3,843. 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 13 minutes is the average flight time from Charleston to Chicago Midway.
Southwest Airlines flies direct from Charleston to Chicago Midway.
As of July 2026, there are 7 flights per week flying from Charleston to Chicago Midway.
The cheapest month to fly from Charleston to Chicago Midway is usually August.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Charleston Airport to Chicago Midway Airport on Tuesday, 11 August 2026.
Yes – the average flight time is 2 hours and 13 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 Chicago Midway 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 Chicago 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 Chicago Midway.

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

  • The average duration of a direct flight from Charleston Airport to Chicago Midway Airport is 2 hours 10 minutes.

  • Chicago is one hour behind Charleston and is in the UTC-6 timezone.

  • Take your pick of six weekly Charleston Airport to Chicago Midway Airport flights. The 05:05 departure with Southwest Airlines is the earliest flight available. Southwest Airlines operates the last service of the day at 20:45.

  • To ensure you get on your CHS to MDW flight, leave enough time for things like check-in and baggage drop. Turning up two hours ahead of international departures and one hour before domestic flights is the standard rule.

  • During popular months like July, you'll want to get to the airport earlier. Arrive two hours before a domestic departure and four hours ahead for international flights when you fly during peak periods in general.

  • Getting to Chicago (and then exploring more of the United States!) is a breeze with Southwest Airlines. This popular airline offers direct flights from Charleston Airport to Chicago Midway Airport.

  • The majority of travellers choose to travel with Southwest Airlines on this route.

  • Southwest Airlines is the most punctual carrier that operates CHS to MDW flights. An exceptional 81.01% of its departures on this route arrive on time.

  • Think about adding a stopover when booking your ticket from Charleston Airport to Chicago Midway Airport. Simply uncheck 'Direct flights only' to break up your trip, or enjoy a detour to a new and interesting place. Here are some options between CHS and MDW:

    • Atlanta Hartsfield-Jackson Airport

    • Charlotte Douglas Airport

    • Cincinnati Northern Kentucky Airport

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

  • R 1,920 is the best price for a one-way Charleston Airport to Chicago Midway Airport flight. Return flights start from R 3,843. These prices may change depending on availability.

  • Don't wait until the last moment. You're more likely to find cheap tickets from CHS to MDW if you book in advance. Airlines often offer some fantastic early bird discounts.

  • May is the cheapest month for flights from Charleston Airport to Chicago Midway Airport. If you're looking to fly at a different time of year, the 'Whole month' tool will give you the lowest airfares for every month.

  • There's no need to check every day to find out if fares have dropped when you create a Price Alert. We'll let you know the moment there's a new deal on cheap flights from CHS to MDW.

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

Handy information about Charleston Airport (CHS)

  • Of the flights that depart from Charleston Airport, 79% touch down on time at their destination.

  • Charleston Airport is about 19 kilometres from central Charleston. If you're driving, catching a taxi or ride-sharing from the centre, it'll take 25 minutes or so to get there, depending on the traffic.

  • Planning to take public transport? Expect a journey time of around 50 minutes.

  • Catching an early flight from Charleston Airport to Chicago Midway Airport? Avoid rushing to the airport (and get some extra shut-eye) by picking one of these stays close to CHS:

Arriving at Chicago Midway Airport (MDW)

Getting from Chicago Midway Airport (MDW) to central Chicago

  • MDW is located at 5700 South Cicero.

  • Chicago Midway Airport is approximately 16 kilometres from the centre of Chicago. The drive time takes about 25 minutes.

  • It'll take around 30 minutes if you're using public transport.

When to fly to Chicago Midway Airport (MDW)

  • July is the most popular month for flights from Charleston Airport to Chicago Midway Airport. For a quieter experience, visit Chicago in December.

  • Before locking in your flight from Charleston Airport to Chicago Midway Airport, think about the kind of weather you enjoy. July is the warmest month in Chicago, with the temperature ranging from 16ºC (61ºF) to 28ºC (82ºF).

  • January sees average temperatures of between -12ºC (10ºF) and 3ºC (37ºF). Search for cheap tickets from CHS to MDW sometime then if you'd rather travel in cooler conditions.

Explore more of the United States

  • Chicago has its own special appeal, but there are so many other parts of the United States you should also see. About 451 kilometres south-east of Chicago, a trip to Columbus will keep you on the go. Don't miss top attractions like Franklin Park Conservatory and Botanical Gardens, Whetstone Park / Park of Roses and Ohio Theatre.

  • Indianapolis is another must-experience destination in the United States and is around 257 kilometres south-east of Chicago. No journey is complete without visiting Lucas Oil Stadium, Eiteljorg Museum and The Children's Museum of Indianapolis.

Prices shown on this page are estimated lowest prices only. Found in the last 12 days.