HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chicago

$105+ 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 9/15. Fares are subject to change and may not be available on all flights or dates of travel.
CHS — CHI
Aug 21 — Aug 281
Fri 8/21
Fri 8/28
1 adult, Economy
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 January or September, booked 52 days in advance, depart on a Friday or Wednesday and return on a Tuesday

Cheap 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 July 22, 2026.

This Kiwi.com deal was found by Cheapflights users on 7/21. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/137:00 am
CHS
-
ORD
2 stops30h 02m
Multiple Airlines
Wed 9/164:49 pm
ORD
-
CHS
1 stop14h 49m
Multiple Airlines
Deal found 7/21$281
This Kiwi.com deal was found by Cheapflights users on 7/22. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/149:44 pm
CHS
-
ORD
2 stops23h 09m
Multiple Airlines
Mon 8/249:10 pm
ORD
-
CHS
1 stop10h 28m
Multiple Airlines
Deal found 7/22$282
This Southwest deal was found by Cheapflights users on 7/21. 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.
Thu 9/1011:30 am
CHS
-
MDW
2 stops9h 00m
Southwest
Mon 9/145:30 am
MDW
-
CHS
2 stops8h 55m
Southwest
Deal found 7/21$283
This Kiwi.com deal was found by Cheapflights users on 7/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/237:47 pm
CHS
-
ORD
1 stop18h 03m
Multiple Airlines
Wed 8/268:05 am
ORD
-
CHS
1 stop27h 59m
Multiple Airlines
Deal found 7/18$283
This Southwest deal was found by Cheapflights users on 7/20. 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.
Wed 8/128:10 am
CHS
-
MDW
2 stops9h 40m
Southwest
Sat 8/153:05 pm
MDW
-
CHS
Nonstop2h 05m
Southwest
Deal found 7/20$284
This United Airlines deal was found by Cheapflights users on 7/22. 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.
Sat 12/194:55 pm
CHS
-
ORD
Nonstop2h 35m
United Airlines
Mon 12/2110:40 am
ORD
-
CHS
Nonstop2h 21m
United Airlines
Deal found 7/22$284
This Kiwi.com deal was found by Cheapflights users on 7/22. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/137:25 am
CHS
-
ORD
2 stops13h 28m
Multiple Airlines
Tue 9/18:05 am
ORD
-
CHS
1 stop9h 09m
Multiple Airlines
Deal found 7/22$285
This Kiwi.com deal was found by Cheapflights users on 7/22. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/137:25 am
CHS
-
ORD
2 stops13h 28m
Multiple Airlines
Wed 9/28:05 am
ORD
-
CHS
1 stop27h 59m
Multiple Airlines
Deal found 7/22$286
This Kiwi.com deal was found by Cheapflights users on 7/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/1111:15 am
CHS
-
ORD
1 stop26h 00m
Multiple Airlines
Fri 8/141:50 pm
ORD
-
CHS
2 stops24h 18m
Multiple Airlines
Deal found 7/18$287
This Kiwi.com deal was found by Cheapflights users on 7/22. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/149:44 pm
CHS
-
ORD
2 stops23h 09m
Multiple Airlines
Wed 8/195:59 pm
ORD
-
CHS
1 stop13h 39m
Multiple Airlines
Deal found 7/22$288
This Delta deal was found by Cheapflights users on 7/18. 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.
Sat 8/86:41 pm
CHS
-
MDW
1 stop4h 55m
Delta
Thu 8/1312:46 pm
MDW
-
CHS
1 stop6h 58m
Delta
Deal found 7/18$289
This Delta deal was found by Cheapflights users on 7/18. 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.
Sat 8/84:56 pm
CHS
-
ORD
1 stop4h 59m
Delta
Tue 8/116:40 am
ORD
-
CHS
1 stop5h 31m
Delta
Deal found 7/18$289

Find 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 July 22, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$281
(Kiwi.com)

One-way from

$105
(Kiwi.com)

Popular in

July

Cheapest in

January

Average price

$409

Good round-trip deal

$351 or less

Good one-way deal

$212 or less
Provider with most accurate pricing for Charleston-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Charleston-Chicago (CHI) flights.
Search Deals
From Charleston to Chicago (CHI)
Search Deals
One-way flight from Charleston to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 3% potential increase in price ($13 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2026
Search Deals
Price to beat on a round-trip flight from Charleston to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Charleston to Chicago (CHI).
Search Deals

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 July 22, 2026.
Use the filters below to find and compare flights from Charleston to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

CharlestonChicago

CHS - MDW

CHSMDW

Charleston

Sat 9/19

8:05 am-5:05 pm

2 stops10h 00m

Chicago Midway

Mon 9/21

8:15 am-3:25 pm

2 stops6h 10m

$283

CharlestonChicago

CHS - MDW

CHSMDW

Charleston

Tue 8/25

5:06 pm-10:36 pm

1 stop6h 30m

Chicago Midway

Thu 8/27

6:05 am-1:11 pm

1 stop6h 06m

$289

CharlestonChicago

CHS - ORD

CHSORD

Charleston

Sat 9/5

10:14 am-2:27 pm

1 stop5h 13m

Chicago O'Hare Intl

Mon 9/7

7:00 am-3:10 pm

1 stop7h 10m

$292

CharlestonChicago

CHS - MDW

CHSMDW

Charleston

Wed 8/12

8:10 am-4:50 pm

2 stops9h 40m

Chicago Midway

Sat 8/15

9:55 am-4:40 pm

1 stop5h 45m

$294

CharlestonChicago

CHS - MDW

CHSMDW

Charleston

Mon 8/17

6:35 am-12:15 pm

2 stops6h 40m

Chicago Midway

Mon 8/24

7:25 am-4:40 pm

2 stops8h 15m

$299

CharlestonChicago

CHS - ORD

CHSORD

Charleston

Thu 10/8

8:00 am-9:32 am

Nonstop2h 32m

Chicago O'Hare Intl

Sun 10/11

6:10 pm-9:33 pm

Nonstop2h 23m

$313

CharlestonChicago

CHS - ORD

CHSORD

Charleston

Fri 8/21

11:40 am-1:13 pm

Nonstop2h 33m

Chicago O'Hare Intl

Mon 8/24

10:33 am-1:58 pm

Nonstop2h 25m

$318

CharlestonChicago

CHS - MDW

CHSMDW

Charleston

Thu 10/8

1:25 pm-7:15 pm

1 stop6h 50m

Chicago Midway

Sun 10/11

7:55 pm-11:00 pm

Nonstop2h 05m

$323

CharlestonChicago

CHS - MDW

CHSMDW

Charleston

Thu 10/8

7:15 pm-8:25 pm

Nonstop2h 10m

Chicago Midway

Mon 10/12

7:50 am-4:10 pm

2 stops7h 20m

$328

CharlestonChicago

CHS - ORD

CHSORD

Charleston

Thu 9/17

8:09 am-9:40 am

Nonstop2h 31m

Chicago O'Hare Intl

Sun 9/20

4:20 pm-7:40 pm

Nonstop2h 20m

$329

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/22

Showing 1-10 of 54 resultsSorted by cheapest first
1
2
3
...
6

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 July.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
PricelinePrice Accuracy1 starTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • 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.

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

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

Currently, September is the cheapest month in which you can book a flight from Charleston to Chicago (average of $325). Flying from Charleston to Chicago in May is currently the most expensive (average of $399). 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 July 22, 2026.

Unlike at noon, 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.

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 July 22, 2026.

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 (16 on average).

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

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 76 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

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 July 18, 2026.

Travelers seeking maximum savings on their Charleston to Chicago flight should consider departing on Saturday 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.

The best insider tips for Charleston to Chicago flights

AI-powered summary based on content written by travel experts. AI can make mistakes.
Cheapflights partnered with top experts to bring you the best recommendations for your Charleston to Chicago trip
Our travel experts
Ramsey Qubein

Ramsey Qubein

Expert on ORD, MDW and CHS

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

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 July 22, 2026.
See what other customers who have flown with Southwest,United Airlines, andAmerican 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.
Southwest
8.0
Very good
4,240 reviews

Comfort

8.0

Entertainment

7.5

Crew

8.6

Overall

8.0

Boarding

8.1

Food

7.0

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers
Southwest
8.0
Very good
4,240 reviews
Southwest
8.0
Very good
4,240 reviews

Comfort

8.0

Entertainment

7.5

Crew

8.6

Overall

8.0

Boarding

8.1

Food

7.0

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers
United Airlines
7.4
Good
10,019 reviews
Southwest
8.0
Very good
4,240 reviews

Comfort

8.0

Entertainment

7.5

Crew

8.6

Overall

8.0

Boarding

8.1

Food

7.0

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers
American Airlines
7.1
Good
11,835 reviews
Southwest
8.0
Very good
4,240 reviews

Comfort

8.0

Entertainment

7.5

Crew

8.6

Overall

8.0

Boarding

8.1

Food

7.0

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers

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 20 outbound flights to Chicago per day. 3 airlines have flights to Chicago from Charleston on a regular basis.

  • How long is the flight from Charleston to Chicago?

    Departing from Charleston to Chicago will take you 5h 13m. 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 Southwest. Our recent data shows that you can find tickets from as low as $190 on this airline. Additional options worth looking into are American Airlines and United Airlines, starting at $204 and $237 round-trip. You may be able to fly from Charleston to Chicago for 47% less than the average price by searching for these airlines.

  • 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 most reliable airlines from Charleston to Chicago?

    The top 3 most reliable airlines when flying from Charleston to Chicago are Qatar Airways (88%), American Airlines (80%) and Alaska Airlines (76%).

  • What are the cheapest flights from Charleston to Chicago?

    On average you can expect to pay $1,759 for a flight from Charleston to Chicago. The cheapest flight overall is $127 while the most popular route, (Charleston - Chicago O'Hare Intl) is currently priced at $237.

  • 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, September is the cheapest month in which you can book a flight from Charleston to Chicago (average of $325). Flying from Charleston to Chicago in May is currently the most expensive (average of $399). 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 Chicago?

Book flights to Chicago if you plan to visit one of these locations
Benton Harbor
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
Porter

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.

Top 3 airlines flying from Charleston to Chicago

Discover the top 3 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 July 22, 2026.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$190Average$308FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$204Average$366FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$237Average$389FlexibilityNo cancel feeOn-time69%

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.