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$121+ 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 7/9. Fares are subject to change and may not be available on all flights or dates of travel.
CHS — CHI
Jun 21 — Jun 281
Sun 6/21
Sun 6/28
1 adult, Economy
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Find cheap flights from Charleston to Chicago with Cheapflights

1. Tell us where you want to go

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Cheapflights Tip: The best prices from Charleston to Chicago are usually found in September or August, booked 83 days in advance, depart on a Friday or Thursday 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 May 22, 2026.

This Southwest deal was found by Cheapflights users on 5/19. 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 6/246:10 am
CHS
-
MDW
Nonstop2h 10m
Southwest
Wed 7/88:20 am
MDW
-
CHS
2 stops6h 50m
Southwest
Deal found 5/19$272
This Southwest deal was found by Cheapflights users on 5/20. 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.
Tue 8/187:35 am
CHS
-
MDW
Nonstop2h 10m
Southwest
Thu 8/208:05 am
MDW
-
CHS
Nonstop2h 20m
Southwest
Deal found 5/20$274
This American Airlines deal was found by Cheapflights users on 5/20. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/127:37 pm
CHS
-
ORD
Nonstop2h 53m
American Airlines
Mon 8/176:57 pm
ORD
-
CHS
Nonstop2h 12m
American Airlines
Deal found 5/20$274
This Kiwi.com deal was found by Cheapflights users on 5/20. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/188:00 am
CHS
-
ORD
2 stops12h 55m
Multiple Airlines
Thu 8/205:30 pm
ORD
-
CHS
1 stop14h 15m
Multiple Airlines
Deal found 5/20$275
This Delta deal was found by Cheapflights users on 5/18. 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.
Wed 9/26:30 am
CHS
-
MDW
1 stop6h 24m
Delta
Tue 9/86:00 am
MDW
-
CHS
1 stop4h 25m
Delta
Deal found 5/18$277
This Delta deal was found by Cheapflights users on 5/20. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/245:10 am
CHS
-
ORD
1 stop6h 03m
Delta
Wed 7/82:07 pm
ORD
-
CHS
1 stop7h 37m
Delta
Deal found 5/20$277
This Southwest deal was found by Cheapflights users on 5/21. 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.
Sat 9/54:35 pm
CHS
-
MDW
1 stop3h 45m
Southwest
Mon 9/76:15 pm
MDW
-
CHS
Nonstop2h 10m
Southwest
Deal found 5/21$279
This Delta deal was found by Cheapflights users on 5/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/2912:57 pm
CHS
-
MDW
1 stop6h 28m
Delta
Sat 8/110:55 am
MDW
-
CHS
1 stop5h 24m
Delta
Deal found 5/21$283
This Southwest deal was found by Cheapflights users on 5/19. 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 6/106:10 am
CHS
-
MDW
Nonstop2h 10m
Southwest
Sat 6/136:10 pm
MDW
-
CHS
Nonstop2h 05m
Southwest
Deal found 5/19$289
This United Airlines deal was found by Cheapflights users on 5/19. 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 7/256:00 am
CHS
-
ORD
Nonstop2h 33m
United Airlines
Tue 7/286:25 pm
ORD
-
CHS
Nonstop2h 23m
United Airlines
Deal found 5/19$289
This Southwest deal was found by Cheapflights users on 5/18. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/27:15 am
CHS
-
MDW
Nonstop2h 15m
Southwest
Wed 6/106:20 pm
MDW
-
CHS
Nonstop2h 05m
Southwest
Deal found 5/18$290
This American Airlines deal was found by Cheapflights users on 5/20. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/28:27 am
CHS
-
ORD
Nonstop2h 33m
American Airlines
Wed 6/107:29 pm
ORD
-
CHS
Nonstop2h 20m
American Airlines
Deal found 5/20$290

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 May 22, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$272
(Southwest)

One-way from

$121
(Kiwi.com)

Popular in

May

Cheapest in

September

Average price

$404

Good round-trip deal

$351 or less

Good one-way deal

$198 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. 10% potential increase in price ($38 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($6 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 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 May 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

Wed 6/17

6:10 am-7:20 am

Nonstop2h 10m

Chicago Midway

Tue 6/23

8:20 am-4:10 pm

2 stops6h 50m

$272

CharlestonChicago

CHS - ORD

CHSORD

Charleston

Wed 6/10

7:47 pm-11:26 pm

1 stop4h 39m

Chicago O'Hare Intl

Tue 6/16

8:40 am-2:27 pm

1 stop4h 47m

$277

CharlestonChicago

CHS - ORD

CHSORD

Charleston

Wed 6/24

5:10 am-10:13 am

1 stop6h 03m

Chicago O'Hare Intl

Wed 7/8

2:07 pm-10:44 pm

1 stop7h 37m

$277

CharlestonChicago

CHS - MDW

CHSMDW

Charleston

Tue 6/16

3:00 pm-8:10 pm

2 stops6h 10m

Chicago Midway

Tue 6/23

8:20 am-4:10 pm

2 stops6h 50m

$287

CharlestonChicago

CHS - ORD

CHSORD

Charleston

Sat 7/11

3:08 pm-4:54 pm

Nonstop2h 46m

Chicago O'Hare Intl

Tue 7/14

6:25 pm-9:48 pm

Nonstop2h 23m

$289

CharlestonChicago

CHS - RFD

CHSRFD

Charleston

Tue 7/7

3:13 pm-9:13 am

1 stop19h 00m

Chicago Greater Rockford

Mon 7/13

7:50 pm-8:38 am

1 stop11h 48m

$304
Quickest round-trip

CharlestonChicago

CHS - MDW

CHSMDW

Charleston

Wed 7/15

6:10 am-7:20 am

Nonstop2h 10m

Chicago Midway

Sat 7/18

1:15 pm-4:25 pm

Nonstop2h 10m

$307

CharlestonChicago

CHS - ORD

CHSORD

Charleston

Sat 6/13

7:47 pm-11:26 pm

1 stop4h 39m

Chicago O'Hare Intl

Tue 6/16

6:30 am-2:27 pm

1 stop6h 57m

$310

CharlestonChicago

CHS - MDW

CHSMDW

Charleston

Tue 6/9

5:10 am-10:09 am

1 stop5h 59m

Chicago Midway

Wed 6/10

6:00 am-12:04 pm

1 stop5h 04m

$320

CharlestonChicago

CHS - MDW

CHSMDW

Charleston

Thu 6/25

5:55 pm-7:10 pm

Nonstop2h 15m

Chicago Midway

Sat 6/27

1:15 pm-4:25 pm

Nonstop2h 10m

$322

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/18

Showing 1-10 of 60 resultsSorted by cheapest first
1
2
3
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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 May.
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 $104). Flying from Charleston to Chicago in March is currently the most expensive (average of $237). 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 May 22, 2026.

Unlike at noon, when flights are generally more expensive, you can save up to 19% 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 May 22, 2026.

The most flights from CHS to CHI are scheduled on a Wednesday (26 on average). You will have fewer flight options on Saturday, 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 74 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 May 16, 2026.

Travelers seeking maximum savings on their Charleston to Chicago flight should consider departing on Friday afternoons 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 May 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
7.9
Good
4,277 reviews

Boarding

8.1

Entertainment

7.5

Crew

8.6

Food

7.0

Overall

7.9

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Southwest
7.9
Good
4,277 reviews
Southwest
7.9
Good
4,277 reviews

Boarding

8.1

Entertainment

7.5

Crew

8.6

Food

7.0

Overall

7.9

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
United Airlines
7.4
Good
9,751 reviews
Southwest
7.9
Good
4,277 reviews

Boarding

8.1

Entertainment

7.5

Crew

8.6

Food

7.0

Overall

7.9

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
American Airlines
7.1
Good
11,644 reviews
Southwest
7.9
Good
4,277 reviews

Boarding

8.1

Entertainment

7.5

Crew

8.6

Food

7.0

Overall

7.9

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

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 22 outbound flights to Chicago per day. 4 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 2h 10m. 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 Delta and Southwest, starting at $166 and $190 round-trip. You may be able to fly from Charleston to Chicago for 61% 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 Spirit Airlines ($80), American Airlines ($102), and Southwest ($118).

  • 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 Envoy Air (92%), Qatar Airways (87%) and American Airlines (84%).

  • What are the cheapest flights from Charleston to Chicago?

    On average you can expect to pay $653 for a flight from Charleston to Chicago. The cheapest flight overall is $132 while the most popular route, (Charleston - Chicago O'Hare Intl) is currently priced at $257.

  • 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 $104). Flying from Charleston to Chicago in March is currently the most expensive (average of $237). 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
Hammond
Porter

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Alternative routes for Charleston to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
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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 May 22, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$135Average$354FlexibilityNo cancel feeOn-time71%
DeltaCheapest$166Average$478FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$190Average$308FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$237Average$388FlexibilityNo cancel feeOn-time69%

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