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 $268 and $414 in February. The cheapest round-trip price found within the last 3 days was $203 on United Airlines (Feb 28-Mar 3).

How long is the flight from Charleston to Chicago?

Departing from Charleston to Chicago will take you 2h 20m. Charleston and Chicago are separated by a distance of 760 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 $249 round-trip. You may be able to fly from Charleston to Chicago for 62% less than the average price by searching for these airlines.

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, August is the cheapest month in which you can book a flight from Charleston to Chicago (average of $245). Flying from Charleston to Chicago in March is currently the most expensive (average of $321). 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 Tuesday evenings when fares are most often at their lowest. Saturday 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 Wednesday (20 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (14 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 $1,879 for a flight from Charleston to Chicago. The cheapest flight overall is $104 while the most popular route, (Charleston - Chicago O'Hare Intl) is currently priced at $133.

What are the most reliable airlines from Charleston to Chicago?

The top 3 most reliable airlines when flying from Charleston to Chicago are ANA (87%), Air Canada (77%) and Air New Zealand (77%).

What is the cheapest day to fly round-trip from Charleston to Chicago?

Leaving on a Thursday is a viable option for saving on travel. Heavily demanded days of the week can typically drive up the prices you see. Booking your travel for a less competitive day can save up to 42% on the overall cost on flights from Charleston to Chicago.

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

Travelers have found it’s best to book a flight 53 days in advance to save up to 67% compared to booking the same week of travel. As your travel date approaches, the cost of this flight route may potentially increase. While opting to book 53 days out may not be an option for all, there are still additional ways to secure a deal in the near future. You might find a flight from Charleston to Chicago 1-2 weeks in advance for as low as $324, or $640 for flights within the next 24 hours.

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

Our data shows that August tends to be the cheapest month to fly to Chicago from Charleston. Users have commonly found prices around $365 for the month, but tickets can be as low as $178. Due to multiple factors, prepare for potentially higher prices in December.

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

Unlike in the afternoon, when flights are generally more expensive, you can save up to 28% on flights from Charleston to Chicago by exploring options for tickets in the evening.

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 17 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.

$64+ Flights from Charleston to Chicago

Round-trip from	$203 (United Airlines)
One-way from	$64 (Cheapflightsfares)
Popular in	December
Cheapest in	August
Average price	$315
Good round-trip deal	$303 or less
Good one-way deal	$175 or less

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$388	FlexibilityNo cancel fee	On-time63%
United Airlines	Cheapest$249	Average$418	FlexibilityNo cancel fee	On-time69%
Delta	Cheapest$368	Average$628	FlexibilityNo cancel fee	On-timeN/A

$64+ 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 12/17. 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 Thursday and return on a Tuesday

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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 September 11, 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 September 11, 2025.

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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

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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 August 29, 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 September 11, 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 September 7, 2025.

Weekly flight availability from Charleston to Chicago

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

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 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 September 11, 2025.