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Cheap flight tickets from Charleston to Chicago

Compare Charleston to Chicago flight deals

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

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Flight deals from Charleston to Chicago

Looking for a cheap last-minute deal or the best return flight from Charleston Airport to Chicago? If you want to travel next month, return fares start from RM940. Find the lowest prices on one-way and return tickets right here.
Chicago.RM508 per passenger.Departing Wed, 24 Jun.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Charleston on Wed, 24 Jun, arriving in Chicago Midway.Price includes taxes and charges.From RM508, select.
Chicago.RM508 per passenger.Departing Wed, 18 Nov.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Charleston on Wed, 18 Nov, arriving in Chicago Midway.Price includes taxes and charges.From RM508, select.
Chicago.RM508 per passenger.Departing Wed, 14 Oct.One-way flight with American Airlines.Outbound direct flight with American Airlines departs from Charleston on Wed, 14 Oct, arriving in Chicago O'Hare International.Price includes taxes and charges.From RM508, select.
Chicago.RM509 per passenger.Departing Wed, 5 Aug.One-way flight with United.Outbound direct flight with United departs from Charleston on Wed, 5 Aug, arriving in Chicago O'Hare International.Price includes taxes and charges.From RM509, select.
Chicago.RM509 per passenger.Departing Tue, 1 Sep.One-way flight with United.Outbound direct flight with United departs from Charleston on Tue, 1 Sep, arriving in Chicago O'Hare International.Price includes taxes and charges.From RM509, select.
Chicago.RM510 per passenger.Departing Wed, 1 Jul.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Charleston on Wed, 1 Jul, arriving in Chicago Midway.Price includes taxes and charges.From RM510, select.
Chicago.RM634 per passenger.Departing Tue, 1 Dec.One-way flight with United.Outbound direct flight with United departs from Charleston on Tue, 1 Dec, arriving in Chicago O'Hare International.Price includes taxes and charges.From RM634, select.
Chicago.RM636 per passenger.Departing Thu, 28 May.One-way flight with United.Outbound direct flight with United departs from Charleston on Thu, 28 May, arriving in Chicago O'Hare International.Price includes taxes and charges.From RM636, select.

Find the cheapest month to fly from Charleston to Chicago

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Charleston to Chicago flights are currently cheapest in June.
May
from RM636
Jun
from RM508
Jul
from RM510
Aug
from RM509
Sep
from RM509
Oct
from RM508
Nov
from RM508
Dec
from RM634
Jan
Find prices
Feb
Find prices
Mar
Find prices
Apr
Find prices

Direct flights from Charleston to Chicago

Alternative Charleston to Chicago routes

Looking for the cheapest, fastest or easiest route from Charleston to Chicago? You could fly into the following airports instead.

Chicago Midway

14km from central Chicago
ClosestCheapest
from RM508
Search flights

Chicago O'Hare International

25km from central Chicago
Cheapest
from RM508
Search flights

Chicago Dupage County

51km from central Chicago
Search flights

Chicago Rockford

126km from central Chicago
from RM719
Search flights

Charleston to Chicago: Flight information

The things to know before you go.
Cheapest flight foundRM508
Cheapest month to flyJune
Average flight time2 hrs, 26 mins
Most popular airlineAmerican Airlines
Average flights per week299

Finding cheap flights from Charleston to Chicago: Frequently asked questions

There are 4 airports in Chicago: Chicago Midway, Chicago O'Hare International, Chicago Dupage County, and Chicago Rockford.
The best price we found for a return flight from Charleston to Chicago is RM940. 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 25 minutes is the average flight time from Charleston to Chicago.
American Airlines, Alaska Airlines and United fly direct from Charleston to Chicago.
As of May 2026, there are 598 flights per week flying from Charleston to Chicago.
The cheapest month to fly from Charleston to Chicago is usually June.
If you're flying from Charleston Airport, the cheapest airport near Chicago is Chicago O'Hare International – which is 25.4 km away from the centre of Chicago. We've found flights into this airport from RM940.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Charleston Airport to Chicago on Wednesday, 17 June 2026.
Yes – the average flight time is 2 hours and 25 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 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.
In May, the average temperature is usually around 13°C. July is typically the warmest month in Chicago, when it usually averages around 26°C. You can expect the least rain in January. The coldest month is January, with temperatures averaging -8°C. The rainiest month is August.
Currently, United offers the cheapest flight tickets to Chicago.

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

  • Take a direct flight from Charleston International Airport to Chicago and you'll be in the air for around 2 hours 15 minutes.

  • Chicago is one hour behind Charleston, where Charleston International Airport is located. Chicago follows the UTC-6 timezone.

  • Charleston International Airport (CHS) to Chicago O'Hare International Airport (ORD) is the most traveled route, with 41 weekly flights to pick from. If you prefer starting your day later, the last flight from CHS to ORD is with American Airlines at 19:44. Go for the first departure operated by American Airlines at 05:00 if you want to fly out earlier.

  • To avoid rushing for your CHS to Chicago flight, leave enough time for things like check-in and baggage drop. Turning up two hours ahead of international departures and an hour before domestic flights is the general travel rule.

  • During popular months such as June, you'll want to get to the airport earlier than usual. Plan to arrive two hours before a domestic departure and four hours ahead of an international flight when you travel during high season in general.

  • Begin your journey at CHS and travel straight to Chicago O'Hare International Airport (ORD). That will be your arrival point when searching for Charleston International Airport to Chicago tickets.

  • Leading airlines that offer direct flights from Charleston International Airport to Chicago include:

  • CHS is about 16 kilometres from central Charleston. If you're ride-sharing, catching a taxi or driving from the centre, it'll take you 25 minutes or so to get there, depending on the traffic. If you're taking public transport, expect the travel time to be around 50 minutes.

  • Want a stress-free start to your holiday? Stay near CHS. Whether you've booked an early flight from Charleston International Airport to Chicago or want to avoid feeling rushed, these hotels are just the thing:

  • When it comes to the on-time performance of Charleston International Airport, 79% of flights arrive within the expected time frame.

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

  • The best price we've found for a one-way Charleston International Airport to Chicago flight is RM508. The cheapest price for a return flight is RM940. Keep in mind fares can change due to demand at the time of booking.

  • Lock in cheap flights from CHS to Chicago by booking one month ahead. Based on our research, that's the sweet spot for bagging a bargain.

  • June is the best month for scoring an amazing deal on Charleston International Airport to Chicago tickets. If you need to travel at a different time of year, the 'Whole month' tool will show you the lowest prices for every month.

  • There's no need to check back in every day to find out if fares have dropped when you create a Price Alert. We'll notify you the moment there's an extra saving on cheap flights from CHS to Chicago.

  • Snag an affordable flight from Charleston International Airport to Chicago with the help of our filters. Select your preferred times, number of stops and airlines, then sort the results by 'Cheapest' for the best deals.

Airports in Chicago

Chicago O'Hare International Airport (ORD)

  • The distance from Chicago O'Hare International Airport (ORD) to central Chicago is roughly 27 kilometres. It'll take you about 30 minutes to reach the centre driving.

  • Travelling by public transport takes around 45 minutes.

  • The last thing you want is a lengthy journey to your hotel if you're getting in late on a flight from Charleston International Airport to Chicago. Stay at one of these accommodation options near ORD instead:

  • Lock in the best rate by booking your ride from Chicago O'Hare International Airport about four weeks ahead of your flight from CHS to Chicago.

  • You'll find ORD at 10000 West O'Hare.

Chicago Midway International Airport (MDW)

  • The centre of Chicago is located around 16 kilometres from Chicago Midway International Airport (MDW). After your flight from Charleston International Airport to Chicago has touched down and you've made your way out of the airport, the drive should take about 25 minutes.

  • The journey will take roughly 30 minutes on public transport.

  • There are some comfortable places to rest your head close to MDW. Settle in and get cosy after your CHS to Chicago flight at any of these well-located options:

  • Secure your first choice, not your last resort. Booking your ride from MDW four weeks in advance often means better deals and a wider choice of vehicles.

  • Chicago Midway International Airport can be found at 5700 South Cicero.

Chicago Rockford International Airport (RFD)

  • Make your way to the city centre after your flight from Charleston International Airport to Chicago has touched down. Central Chicago is about 145 kilometres from Chicago Rockford International Airport (RFD) and takes roughly 1 hour 40 minutes to reach by car.

  • The journey will take you roughly 2 hours on public transport.

  • If you don't want to make the trip into the centre, find a hotel near RFD. Get comfortable at one of these options after your CHS to Chicago flight:

  • Booking a couple of weeks in advance of your flight from Charleston International Airport to Chicago is always smart. Along with more affordable prices, you'll get a better selection of vehicle makes and models at RFD.

  • Chicago Rockford International Airport is located at 2 Airport Cir.

Best time to go to Chicago

  • It's time to work out your dates for your flight from Charleston International Airport to Chicago. July is the most popular month to visit Chicago. If you like a quieter vibe, go in January.

  • Before locking in your Charleston International Airport to Chicago plane ticket, think about what kind of weather you prefer. July is the warmest month in Chicago, with temperatures ranging from 16ºC (61ºF) to 28ºC (82ºF).

  • Search for cheap tickets from CHS to Chicago in January if you want to travel in cooler conditions. Temperatures are at their lowest then, ranging between -12ºC (10ºF) and 3ºC (37ºF) on average.

More about Chicago

  • Start your Chicago trip off on the right foot by choosing the ideal place to stay. After booking your flight from Charleston International Airport to Chicago, check out our range of accommodation options including:

  • There are so many things to discover in this city it can be hard to figure out where to begin. Art Institute of Chicago, Millennium Park and Willis Tower are top attractions which should feature on any good Chicago itinerary.

Explore more of the United States

  • Columbus is just one of the many places in the United States waiting to be explored once you've seen the sights of Chicago. Around 451 kilometres away to the southeast, its best attractions include Franklin Park Conservatory and Botanical Gardens, Whetstone Park / Park of Roses and Ohio Theatre.

  • If you're interested in discovering another major stop in the United States, consider Indianapolis, about 257 kilometres southeast of Chicago. Lucas Oil Stadium, Eiteljorg Museum and The Children's Museum of Indianapolis are key reasons to visit.

Plan the rest of your trip from Charleston to Chicago

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