Cheap Flights from Charleston SC to Chicago Midway IL from $222

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Flight deals from Charleston Airport to Chicago Midway Airport

Looking for a cheap last-minute deal or the best round-trip flight from Charleston Airport to Chicago Midway Airport? If you want to travel next month, round-trip fares start from $222. Find the lowest prices on one-way and round-trip tickets right here.

Chicago.$222 per passenger.Departing Wed, Apr 8, returning Sat, Apr 11.Round-trip flight with Spirit Airlines and Frontier Airlines.Outbound indirect flight with Spirit Airlines, departing from Charleston on Wed, Apr 8, arriving in Chicago Midway.Inbound indirect flight with Frontier Airlines, departing from Chicago Midway on Sat, Apr 11, arriving in Charleston.Price includes taxes and charges.From $222, select.

Chicago.$236 per passenger.Departing Wed, May 13, returning Sun, May 17.Round-trip flight with Breeze Airways and Frontier Airlines.Outbound indirect flight with Breeze Airways, departing from Charleston on Wed, May 13, arriving in Chicago Midway.Inbound indirect flight with Frontier Airlines, departing from Chicago Midway on Sun, May 17, arriving in Charleston.Price includes taxes and charges.From $236, select.

Chicago.$239 per passenger.Departing Tue, Mar 10, returning Tue, Mar 17.Round-trip flight with Breeze Airways and Frontier Airlines.Outbound indirect flight with Breeze Airways, departing from Charleston on Tue, Mar 10, arriving in Chicago Midway.Inbound indirect flight with Frontier Airlines, departing from Chicago Midway on Tue, Mar 17, arriving in Charleston.Price includes taxes and charges.From $239, select.

Chicago.$254 per passenger.Departing Fri, Mar 27, returning Sat, Apr 4.Round-trip flight with Spirit Airlines and Frontier Airlines.Outbound indirect flight with Spirit Airlines, departing from Charleston on Fri, Mar 27, arriving in Chicago Midway.Inbound indirect flight with Frontier Airlines, departing from Chicago Midway on Sat, Apr 4, arriving in Charleston.Price includes taxes and charges.From $254, select.

Chicago.$265 per passenger.Departing Thu, Apr 30, returning Sun, May 3.Round-trip flight with Breeze Airways and Frontier Airlines.Outbound indirect flight with Breeze Airways, departing from Charleston on Thu, Apr 30, arriving in Chicago Midway.Inbound indirect flight with Frontier Airlines, departing from Chicago Midway on Sun, May 3, arriving in Charleston.Price includes taxes and charges.From $265, select.

Chicago.$271 per passenger.Departing Sat, Apr 25, returning Mon, Apr 27.Round-trip flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departing from Charleston on Sat, Apr 25, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departing from Chicago Midway on Mon, Apr 27, arriving in Charleston.Price includes taxes and charges.From $271, select.

Chicago.$293 per passenger.Departing Tue, May 26, returning Mon, Jun 1.Round-trip flight with Breeze Airways and Frontier Airlines.Outbound indirect flight with Breeze Airways, departing from Charleston on Tue, May 26, arriving in Chicago Midway.Inbound indirect flight with Frontier Airlines, departing from Chicago Midway on Mon, Jun 1, arriving in Charleston.Price includes taxes and charges.From $293, select.

Chicago.$324 per passenger.Departing Wed, May 13, returning Sun, May 17.Round-trip flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departing from Charleston on Wed, May 13, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departing from Chicago Midway on Sun, May 17, arriving in Charleston.Price includes taxes and charges.From $324, select.

Chicago.$365 per passenger.Departing Thu, Jul 9, returning Mon, Jul 13.Round-trip flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departing from Charleston on Thu, Jul 9, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departing from Chicago Midway on Mon, Jul 13, arriving in Charleston.Price includes taxes and charges.From $365, select.

Chicago.$365 per passenger.Departing Thu, Jun 4, returning Sun, Jun 7.Round-trip flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departing from Charleston on Thu, Jun 4, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departing from Chicago Midway on Sun, Jun 7, arriving in Charleston.Price includes taxes and charges.From $365, select.

Chicago.$369 per passenger.Departing Fri, Oct 2, returning Mon, Oct 5.Round-trip flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departing from Charleston on Fri, Oct 2, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departing from Chicago Midway on Mon, Oct 5, arriving in Charleston.Price includes taxes and charges.From $369, select.

Chicago.$389 per passenger.Departing Tue, May 26, returning Mon, Jun 1.Round-trip flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departing from Charleston on Tue, May 26, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departing from Chicago Midway on Mon, Jun 1, arriving in Charleston.Price includes taxes and charges.From $389, select.

Chicago.$418 per passenger.Departing Fri, Jul 31, returning Mon, Aug 3.Round-trip flight with Delta.Outbound indirect flight with Delta, departing from Charleston on Fri, Jul 31, arriving in Chicago Midway.Inbound indirect flight with Delta, departing from Chicago Midway on Mon, Aug 3, arriving in Charleston.Price includes taxes and charges.From $418, select.

Chicago.$470 per passenger.Departing Wed, Mar 18, returning Mon, Mar 23.Round-trip flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departing from Charleston on Wed, Mar 18, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departing from Chicago Midway on Mon, Mar 23, arriving in Charleston.Price includes taxes and charges.From $470, select.

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 April.

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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 found	$222
Cheapest month to fly	April
Average flight time	2 hrs, 14 mins
Most popular airline	Southwest Airlines
Average flights per week	10

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

How much are round-trip flights from Charleston to Chicago Midway?

The best price we found for a round-trip flight from Charleston to Chicago Midway is $222. 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.

How long does it take to fly from Charleston to Chicago Midway?

2 hours and 14 minutes is the average flight time from Charleston to Chicago Midway.

Which airlines fly direct from Charleston to Chicago Midway?

Southwest Airlines flies direct from Charleston to Chicago Midway.

How many flights are there a week from Charleston to Chicago Midway?

There are 10 flights per week flying from Charleston to Chicago Midway, as of March 2026.

When is the cheapest time to fly from Charleston to Chicago Midway?

The cheapest month to fly from Charleston to Chicago Midway is usually April.

Which upcoming date is cheapest to fly from Charleston Airport to Chicago Midway Airport on?

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 Wednesday, April 8, 2026.

Can I get a direct flight from Charleston Airport to Chicago Midway Airport?

Yes – the average flight time is 2 hours and 14 minutes.

How can I find the best flight deal to Chicago Midway?

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.

When is the best time to book flights to Chicago?

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.

Which is the cheapest airline to fly with from Charleston Airport to Chicago Midway?

Currently, Spirit Airlines and Southwest Airlines offer the cheapest flight tickets to Chicago Midway.

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

Hop on a direct flight from Charleston International Airport to Chicago Midway International Airport and you'll be in the air for an average of 2 hours 15 minutes.
Chicago's timezone is UTC-5, which makes Chicago one hour behind Charleston.
Every week, there are five Charleston International Airport to Chicago Midway International Airport flights. If you prefer to take off as soon as possible, select the 05:40 Southwest Airlines flight. If you'd rather make the most of your day before flying, the latest flight is at 20:40 with Southwest Airlines.
Arriving two hours before an international flight and one hour ahead of a domestic departure are golden rules for hassle-free flying. Make sure you're at the airport on time to catch your CHS to MDW flight.
Traveling during a peak month like July? Major public holidays and other popular seasons can lead to longer queues at check-in and security. Play things extra safe and get there up to four hours before international flights and two hours before a domestic departure.
Southwest Airlines is your gateway to discovering Chicago (and maybe even some other great corners of United States!). Browse the direct flights from Charleston International Airport to Chicago Midway International Airport offered by this popular carrier.
The majority of travelers choose to fly with Southwest Airlines on this route.
Southwest Airlines is the most punctual carrier that offers CHS to MDW flights. An impressive 94.12% of its departures on this route arrive as scheduled.
Consider adding a stopover when booking your ticket from Charleston International Airport to Chicago Midway International Airport. Simply deselect 'Direct flights only' to break up your journey, or even explore someplace new along the way. Here are some options between CHS and MDW:
- Hartsfield-Jackson Atlanta International Airport
- Cincinnati/Northern Kentucky Airport
- Charlotte Douglas International Airport

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

$64 is currently the best price for a one-way Charleston International Airport to Chicago Midway International Airport flight. A return flight starts from $222. These fares can change depending on demand and availability.
Get cheap tickets from CHS to MDW by booking at least six months ahead. According to our research, that's the sweet spot for bagging a bargain.
Plan your trip for May. That's the cheapest month for flights from Charleston International Airport to Chicago Midway International Airport. If you're flexible with your dates, try out the 'Whole month' tool to see the lowest airfare across each month.
Cut down on the time spent looking for cheap flights from CHS to MDW by creating a Price Alert. We'll send you an email or push notification on the app when fares go down.
Discover the perfect flight for you by using the filters. To see the 'Cheapest,' 'Best' or 'Fastest' flights from Charleston International Airport to Chicago Midway International Airport, use the 'Sort by' tool. You can also filter results by departure and arrival times, airline, and journey duration.

Handy information about Charleston International Airport (CHS)

Charleston International Airport has a strong on-time record, reducing your chances of a delayed flight. Departures from CHS arrive at their destination as scheduled 81.5% of the time.
To reach Charleston International Airport from central Charleston, it takes around 30 minutes if you're planning to drive. Of course, this depends on traffic conditions. It's approximately 21 kilometers from the airport to the city center.
Expect a trip time of about 3 hours 35 minutes when using public transport.
Need a convenient hotel near CHS? If you've booked an early flight from Charleston International Airport to Chicago Midway International Airport, these stays will have you sleeping moments from check-in:

Arriving at Chicago Midway International Airport (MDW)

The last thing you want is a long journey to your hotel if you're getting in late on a Charleston International Airport to Chicago Midway International Airport flight. Reserve one of these accommodation options near MDW instead:
Go wherever you want, whenever you want with a Chicago Midway International Airport rental car. Pick up a set of wheels from Dollar, Hertz or Budget and venture far and wide through Chicago and beyond.
Booking your ride from Chicago Midway International Airport around four weeks ahead can help you get the lowest rate.

Getting from Chicago Midway International Airport (MDW) to central Chicago

MDW is located at 5700 South Cicero.
From Chicago Midway International Airport, Chicago is approximately 19 kilometers away. It takes around 20 minutes to get to the center driving.
When traveling by public transport, expect a journey of roughly 45 minutes.

When to fly to Chicago Midway International Airport (MDW)

July is the busiest month for flights from Charleston International Airport to Chicago Midway International Airport. For smaller crowds, go to Chicago in May.
When booking your flight from Charleston International Airport to Chicago Midway International Airport, consider the type of weather you like. July is the warmest month in Chicago, with the temperature ranging from 15ºC (59ºF) to 29ºC (84ºF).
January has average temperatures of between -12ºC (10ºF) and 3ºC (37ºF). Search for cheap tickets from CHS to MDW around that time if you want to travel in cooler conditions.

Explore more of United States

You've seen Chicago, now it's time to discover other parts of United States. Journey around 451 kilometers south-east to Columbus to check off its leading sights. From Franklin Park Conservatory and Botanical Gardens to Ohio Statehouse and German Village, there's plenty to keep you busy.
Indianapolis is another sought-after destination in United States and is around 257 kilometers south-east of Chicago. No trip is complete without seeing The Children's Museum of Indianapolis, Indianapolis Museum of Art and Indianapolis Zoo.