How much does it cost to fly round-trip from Charleston to Chicago?

Airfare is below average for this route at the moment. Charleston to Chicago flights typically cost between $298 and $496 in October. The cheapest round-trip price found within the last 3 days was $222 on Multiple Airlines (Oct 31-Nov 9).

How long is the flight from Charleston to Chicago?

Departing from Charleston to Chicago will take you 2h 15m. Charleston and Chicago are separated by a distance of 745 mi. Both multi-stop and nonstop flights can be found to your destination and back.

What are the cheapest airlines flying from Charleston to Chicago round-trip?

Our cheapest airline available from Charleston to Chicago is American Airlines. Our recent data shows that you can find tickets from as low as $135 on this airline. Additional options worth looking into are Southwest and United Airlines, starting at $190 and $251 round-trip. You may be able to fly from Charleston to Chicago for 63% less than the average price by searching for these airlines.

What are the cheapest airlines to fly from Charleston to Chicago one-way?

The cheapest airlines for a one-way flight from Charleston to Chicago are United Airlines ($73), Southwest ($76), and Delta ($101).

How far ahead should I book a flight from Charleston to Chicago?

The price you pay for your flight from Charleston to Chicago may vary depending on when you book. For the best chance of a lower fare, look to book 65 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

What is the cheapest month to book a flight from Charleston to Chicago?

Currently, April is the cheapest month in which you can book a flight from Charleston to Chicago (average of $76). Flying from Charleston to Chicago in February is currently the most expensive (average of $228). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest day to fly from Charleston to Chicago?

Travelers seeking maximum savings on their Charleston to Chicago flight should consider departing on Friday afternoons when fares are most often at their lowest. Tuesday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from Charleston to Chicago

The most flights from CHS to CHI are scheduled on a Monday (24 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (7 on average).

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

What are the most popular routes from Charleston to Chicago?

Most travelers choose Charleston - Chicago O'Hare Intl, Charleston - Chicago Midway or Charleston - Chicago Greater Rockford when deciding on the best route from Charleston to Chicago.

What are the cheapest flights from Charleston to Chicago?

On average you can expect to pay $1,814 for a flight from Charleston to Chicago. The cheapest flight overall is $138 while the most popular route, (Charleston - Chicago O'Hare Intl) is currently priced at $124.

What are the most reliable airlines from Charleston to Chicago?

The top 3 most reliable airlines when flying from Charleston to Chicago are Qatar Airways (94%), ANA (87%) and Air Canada (83%).

What are the most popular airlines that fly from Charleston to Chicago?

Consider United Airlines, American Airlines or Southwest when booking your flight. These represent the most popular airlines when flying from Charleston to Chicago.

What is the cheapest time of day to fly from CHS to CHI?

Unlike in the morning, when flights are generally more expensive, you can save up to 13% on flights from Charleston to Chicago by exploring options for tickets at noon.

Most accurate provider : When it comes to deals on Charleston-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Charleston-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Charleston-Chicago flight searches over the past month and is updated monthly.

Most trusted provider : When it comes to deals on Charleston-Chicago flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Charleston-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

What airport do you fly from for flights from Charleston to Chicago?

For a flight from Charleston to Chicago, you will be flying from Charleston. Charleston (CHS) is just 10.2 mi from the center of the city. Charleston is the only Charleston airport and it handles 20 outbound flights to Chicago per day. 4 airlines have flights to Chicago from Charleston on a regular basis.

Can I find deals for flights from Charleston to Chicago that include hotel bookings?

Yes. In addition to deals on Charleston to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

How can I find direct flights from Charleston to Chicago?

After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Charleston to Chicago.

Can I find deals for business class flights from Charleston to Chicago?

Yes. Cheapflights offers flight deals from Charleston to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

$55+ Flights from Charleston to Chicago

Most accurate provider	FlightHub 3 stars
Most trusted provider	FlightHub 3 stars
Round-trip from	$222 (Kiwi.com)
One-way from	$55 (Priceline)
Popular in	December
Cheapest in	August
Average price	$349
Good round-trip deal	$294 or less
Good one-way deal	$184 or less

Provider	Price Accuracy	Trust Score*
Expedia	Price Accuracy2 stars	Trust Score*3 stars
FlightHub	Price Accuracy3 stars	Trust Score*3 stars
eDreams	Price Accuracy3 stars	Trust Score*3 stars

CHS

Expect long security lines during early-morning departures when most gates have flights leaving simultaneously.

ORD

Use the free shuttle train outside security to navigate between ORD terminals efficiently.

MDW

Take the 'L' train from MDW for a quick, 30-minute ride to downtown Chicago.

Airline	Cheapest	Average	Flexibility	On-time
American Airlines	Cheapest$135	Average$349	FlexibilityNo cancel fee	On-time71%
Southwest	Cheapest$190	Average$377	FlexibilityNo cancel fee	On-time63%
United Airlines	Cheapest$251	Average$419	FlexibilityNo cancel fee	On-time69%
Delta	Cheapest$368	Average$628	FlexibilityNo cancel fee	On-timeN/A

$55+ Cheap flights from Charleston (CHS) to Chicago (CHI)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 1/8. Fares are subject to change and may not be available on all flights or dates of travel.

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Cheapflights Tip: The best prices from Charleston to Chicago are usually found in August or September, booked 65 days in advance, depart on a Friday or Saturday and return on a Tuesday

Cheap flight deals from Charleston to Chicago

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Cheapest flights from Charleston to ChicagoExplore the most affordable flight options available from Charleston to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 22, 2025.

Explore the most affordable flight options available from Charleston to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 22, 2025.

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Use the filters below to find and compare flights from Charleston to Chicago that are best for you.

Compare providers for flights from Charleston to Chicago

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.

Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Charleston to Chicago in October.

Best time to book a flight from Charleston to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Charleston with our price prediction graph.

Cheapflights Insights

Everything you need to know about your flight from Charleston to Chicago

How far ahead should I book a flight from Charleston to Chicago?

Use this chart to determine the optimal time to book a round-trip flight from Charleston to Chicago. Price data was last updated on October 17, 2025.

What is the cheapest month to book a flight from Charleston to Chicago?

What is the cheapest time of day to fly from CHS to CHI?

Find hourly flight availability from Charleston to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated October 22, 2025.

What is the cheapest day to fly from Charleston to Chicago?

Use this chart to determine the cheapest time to fly round-trip from Charleston to Chicago. Price data was last updated on October 19, 2025.

Weekly flight availability from Charleston to Chicago

Explore weekly flight availability from Charleston to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated October 22, 2025.

How much does it cost to fly round-trip from Charleston to Chicago?

The best insider tips for Charleston to Chicago flights

Cheapflights partnered with top experts to bring you the best recommendations for your Charleston to Chicago trip

Airports

CHS

ORD

MDW

Our travel experts

Reviews of airlines servicing Chicago

See what other customers who have flown with Southwest, Delta, and United Airlines from Charleston to Chicago have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.

Related info for your journey

Find useful and relevant information for your journey from Charleston to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

What airport do you fly from for flights from Charleston to Chicago?

How long is the flight from Charleston to Chicago?

What are the cheapest airlines flying from Charleston to Chicago round-trip?

What are the cheapest airlines to fly from Charleston to Chicago one-way?

What are the most popular routes from Charleston to Chicago?

What are the most reliable airlines from Charleston to Chicago?

What are the cheapest flights from Charleston to Chicago?

Can I find deals for flights from Charleston to Chicago that include hotel bookings?

How can I find direct flights from Charleston to Chicago?

Can I find deals for business class flights from Charleston to Chicago?

What is the cheapest month to book a flight from Charleston to Chicago?

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Cheapest flights from Charleston to Chicago
Explore the most affordable flight options available from Charleston to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 22, 2025.