Chicago

$91+ 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 9/4. Fares are subject to change and may not be available on all flights or dates of travel.
CHS — CHI
jul 7 — jul 141
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Charleston to Chicago with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheapflights Tip: The best prices from Charleston to Chicago are usually found in September or October, booked 89 days in advance, depart on a Friday or Thursday and return on a Tuesday

Cheap flight deals from Charleston to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Charleston (CHS) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated julho 2, 2025.

Round-trip from

$203
(Southwest)

One-way from

$91
(Southwest)

Popular in

December

Cheapest in

September

Average price

$326

Good round-trip deal

$306 or less

Good one-way deal

$139 or less
From Charleston to Chicago (CHI)
One-way flight from Charleston to Chicago (CHI)
Highest demand for flights based on searches. 5% potential increase in price ($22 potential increase over avg. RT price).
Cheapest flight prices on average. 1% potential price decrease ($5 potential savings vs. average RT price).
Average for round-trip flights in July 2025
Price to beat on a round-trip flight from Charleston to Chicago (CHI).
Price to beat on a one-way flight from Charleston to Chicago (CHI).

Find flight deals from Charleston to Chicago

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 julho 2, 2025.

This Southwest deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
qui 8/214:25 pmCHS - MDW
1 stop8h 40mSouthwest
dom 8/248:25 amMDW - CHS
Nonstop2h 10mSouthwest
Deal found 7/2$203
This American Airlines deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
seg 8/47:22 amCHS - ORD
Nonstop2h 26mAmerican Airlines
sex 8/86:03 amORD - CHS
1 stop4h 28mAmerican Airlines
Deal found 7/2$203
This Southwest deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
qua 8/138:35 amCHS - ORD
2 stops13h 55mSouthwest
seg 8/187:00 amORD - CHS
1 stop7h 35mSouthwest
Deal found 7/1$206
This Cheapflightsfares deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb 8/29:48 pmCHS - ORD
1 stop12h 07mSpirit Airlines
seg 8/45:05 amORD - CHS
1 stop8h 40mSpirit Airlines
Deal found 7/1$211
This Delta deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sex 8/295:35 pmCHS - MDW
1 stop5h 09mDelta
ter 9/26:00 amMDW - CHS
1 stop4h 50mDelta
Deal found 7/1$213
This Delta deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
qui 8/216:59 pmCHS - ORD
1 stop5h 57mDelta
dom 8/245:45 amORD - CHS
1 stop7h 05mDelta
Deal found 7/2$213
This United Airlines deal was found by Cheapflights users on 6/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sex 8/294:34 pmCHS - ORD
Nonstop2h 36mUnited Airlines
seg 9/17:15 amORD - CHS
Nonstop2h 25mUnited Airlines
Deal found 6/30$228

Cheapflights Fare Finder

Customize your flight search to find flights from Charleston to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated julho 2, 2025.
Use the filters below to find and compare flights from Charleston to Chicago that are best for you.

Fly from

Charleston

Fly to

Chicago

Route

Depart

Return

Price

CharlestonChicago

CHS - MDW

CHSMDW

Charleston

qui 8/21

4:25 pm-12:05 am

1 stop8h 40m

Chicago Midway

dom 8/24

8:25 am-11:35 am

Nonstop2h 10m

$203

CharlestonChicago

CHS - ORD

CHSORD

Charleston

seg 8/4

6:00 am-11:50 am

1 stop6h 50m

Chicago O'Hare Intl

seg 8/4

8:24 pm-11:59 pm

Nonstop2h 35m

$203

CharlestonChicago

CHS - ORD

CHSORD

Charleston

qua 8/13

8:35 am-9:30 pm

2 stops13h 55m

Chicago O'Hare Intl

seg 8/18

7:00 am-3:35 pm

1 stop7h 35m

$206

CharlestonChicago

CHS - ORD

CHSORD

Charleston

sáb 8/2

9:48 pm-8:55 am

1 stop12h 07m

Chicago O'Hare Intl

seg 8/4

5:05 am-2:45 pm

1 stop8h 40m

$211

CharlestonChicago

CHS - MDW

CHSMDW

Charleston

sex 8/29

5:35 pm-9:44 pm

1 stop5h 09m

Chicago Midway

sáb 8/30

4:25 pm-11:51 pm

1 stop6h 26m

$213

CharlestonChicago

CHS - ORD

CHSORD

Charleston

qui 8/21

6:59 pm-11:56 pm

1 stop5h 57m

Chicago O'Hare Intl

dom 8/24

5:45 am-11:50 am

1 stop5h 05m

$213

CharlestonChicago

CHS - ORD

CHSORD

Charleston

sex 8/29

4:34 pm-6:10 pm

Nonstop2h 36m

Chicago O'Hare Intl

seg 9/1

7:15 am-10:40 am

Nonstop2h 25m

$228

CharlestonChicago

CHS - MDW

CHSMDW

Charleston

qui 9/4

5:30 am-6:35 am

Nonstop2h 05m

$91

CharlestonChicago

CHS - ORD

CHSORD

Charleston

qua 9/17

6:05 am-7:33 am

Nonstop2h 28m

$91

CharlestonChicago

CHS - MDW

CHSMDW

Charleston

ter 9/30

4:44 pm-9:36 pm

1 stop5h 52m

$101

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/30

Showing 1-10 of 20 results
1
2

The best insider tips for Charleston to Chicago flights

Snippets provided in this section are AI-generated based on a summarization of Cheapflights-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
Cheapflights partnered with top experts to bring you the best recommendations for your Charleston to Chicago trip
Airlines
United Airlines

United's Economy Plus offers extra legroom seats towards the front of the economy cabin.


United's Polaris Business Class features lie-flat seats, noise-reducing headphones, and large entertainment screens.

Southwest

Southwest offers two free checked bags, including oversized items like skis or golf clubs.


Enjoy free in-flight entertainment with early-release movies and live TV on Southwest flights.

Airports
CHS

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

Read more about CHSby Ramsey Qubein
ORD

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

Read more about ORDby Ramsey Qubein
MDW

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

Read more about MDWby Ramsey Qubein
Our travel experts
Harriet Baskas

Harriet Baskas

Expert on United Airlines

Harriet Baskas

Harriet Baskas

Harriet is an award-winning journalist who is happiest in an airport or an unusual museum. Her stories about airports, air travel, and the business of travel have appeared on NBC News, CNBC, USA TODAY, The Points Guy and other outlets. She is the creator of the StuckatTheAirport.com blog and the author of nine books. When not out on the road or exploring the latest airport amenities, she’s home in Seattle getting ready for the next adventure.

Read more
Marisa Garcia

Marisa Garcia

Expert on Southwest

Marisa Garcia

Marisa Garcia

Marisa knows planes inside and out, spending 16 years working on aircraft in hangars at airports around the world. She is an aviation industry expert, specialized in airline interiors and regulations. Ten years ago, she pivoted to journalism. She shares her insights in leading aviation, travel, and business publications and on her site FlightChic.

Read more
Ramsey Qubein

Ramsey Qubein

Expert on ORD, MDW and CHS

Ramsey Qubein

Ramsey Qubein

An avid traveler and aviation expert who has visited 173 countries, all 50 states and seven continents, Ramsey Qubein flies nearly 400,000 miles a year. As a North Carolina-based freelance journalist for publications including Conde Nast Traveler, Forbes, USA Today and Bloomberg among others, he explores the latest trends in aviation, hospitality, cruises and business.

Read more

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.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

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 June 27, 2025.

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 89 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 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 julho 2, 2025.

Unlike in the afternoon, when flights are generally more expensive, you can save up to 32% on flights from Charleston to Chicago by exploring options for tickets in the evening.

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 June 29, 2025.

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

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 julho 2, 2025.

The most flights from CHS to CHI are scheduled on a Monday (20 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (5 on average).

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

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated julho 2, 2025.
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.

Entertainment

7.6

Food

7.0

Crew

8.6

Comfort

8.0

Boarding

8.2

Overall

8.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

Entertainment

7.6

Food

7.0

Crew

8.6

Comfort

8.0

Boarding

8.2

Overall

8.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
8.0
Very good

Entertainment

7.6

Food

7.0

Crew

8.6

Comfort

8.0

Boarding

8.2

Overall

8.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

Entertainment

7.6

Food

7.0

Crew

8.6

Comfort

8.0

Boarding

8.2

Overall

8.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

Entertainment

7.6

Food

7.0

Crew

8.6

Comfort

8.0

Boarding

8.2

Overall

8.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

Entertainment

7.6

Food

7.0

Crew

8.6

Comfort

8.0

Boarding

8.2

Overall

8.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

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?

    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 12 outbound flights to Chicago per day. 4 airlines have flights to Chicago from Charleston on a regular basis.

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

    Our cheapest airline available from Charleston to Chicago is Southwest. Our recent data shows that you can find tickets from as low as $203 on this airline. Additional options worth looking into are American Airlines and Spirit Airlines, starting at $203 and $211 round-trip. You may be able to fly from Charleston to Chicago for 44% 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 Southwest ($91), United Airlines ($91), and Delta ($101).

  • What are the most popular routes from Charleston to Chicago?

  • What are the most reliable airlines from Charleston to Chicago?

    The top 3 most reliable airlines when flying from Charleston to Chicago are ANA (91%), Air Canada (84%) and Air New Zealand (84%).

  • What are the cheapest flights from Charleston to Chicago?

    On average you can expect to pay $1,971 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 $181.

  • 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.

  • 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.

See more FAQs

Traveling to a place near Charleston?

Book flights to Charleston if you plan to visit one of these locations
Merrillville
Lansing
Benton Harbor
Porter
Hammond
Valparaiso
Chesterton

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Charleston to Chicago

See prices for flight routes from nearby airports that may be better suited for you.

Top 4 airlines flying from Charleston to Chicago

Discover the top 4 airlines that operate flights from Charleston to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated julho 2, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$81Average$158FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$247Average$356FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$261Average$418FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$279Average$407FlexibilityNo cancel feeOn-time63%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.