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$69+ 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 3/5. Fares are subject to change and may not be available on all flights or dates of travel.
CHS — CHI
Jan 21 — Jan 281
Tue 1/21
Tue 1/28
1 adult, Economy
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The best prices from Charleston to Chicago are usually found in May or October, booked 89 days in advance, depart on a Thursday or Wednesday and return on a Saturday

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 January 16, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$335
(Southwest)

One-way from

$69
(Cheapflightsfares)

Popular in

February

Cheapest in

May

Average price

$373
Provider with most accurate pricing for Charleston-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Charleston-Chicago (CHI) flights.
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From Charleston to Chicago (CHI)
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One-way flight from Charleston to Chicago (CHI)
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High demand for flights, 6% potential price rise
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Best time to find cheap flights, 1% potential price drop
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Average for round-trip flights in January 2025
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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 January 16, 2025.

This Southwest deal was found by Cheapflights users on 1/15. 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 2/198:50 amCHS - MDW
1 stop9h 05mSouthwest
Sun 2/234:20 pmMDW - CHS
Nonstop2h 00mSouthwest
Deal found 1/15$335
This American Airlines deal was found by Cheapflights users on 1/16. 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.
Fri 2/215:25 pmCHS - ORD
1 stop6h 19mAmerican Airlines
Mon 2/241:12 pmORD - CHS
Nonstop2h 06mAmerican Airlines
Deal found 1/16$335
This Mytrip deal was found by Cheapflights users on 1/15. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/112:15 pmCHS - ORD
2 stops20h 29mSpirit Airlines
Sun 3/169:16 amORD - CHS
3 stops26h 53mSpirit Airlines
Deal found 1/15$339
This JetBlue deal was found by Cheapflights users on 1/15. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/2211:15 amCHS - ORD
1 stop8h 28mJetBlue
Wed 10/19:50 amORD - CHS
1 stop5h 48mJetBlue
Deal found 1/15$342
This Mytrip deal was found by Cheapflights users on 1/15. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/99:31 pmCHS - ORD
1 stop12h 57mMultiple Airlines
Thu 3/135:22 pmORD - CHS
3 stops28h 35mMultiple Airlines
Deal found 1/15$343
This Southwest deal was found by Cheapflights users on 1/16. 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 2/1911:30 amCHS - ORD
2 stops11h 00mSouthwest
Sat 2/227:00 amORD - CHS
2 stops13h 55mSouthwest
Deal found 1/16$344
This Delta deal was found by Cheapflights users on 1/16. 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.
Fri 2/285:35 amCHS - MDW
1 stop5h 37mDelta
Mon 3/312:44 pmMDW - CHS
1 stop4h 16mDelta
Deal found 1/16$345
This Delta deal was found by Cheapflights users on 1/16. 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.
Sun 3/25:35 amCHS - ORD
1 stop3h 55mDelta
Mon 3/36:45 amORD - CHS
1 stop4h 40mDelta
Deal found 1/16$345
This United Airlines deal was found by Cheapflights users on 1/16. 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.
Thu 3/1311:25 amCHS - ORD
Nonstop2h 37mUnited Airlines
Sun 3/167:10 amORD - CHS
Nonstop2h 14mUnited Airlines
Deal found 1/16$349
This Mytrip deal was found by Cheapflights users on 1/15. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/27:10 amCHS - MDW
2 stops11h 20mMultiple Airlines
Sun 3/96:26 pmMDW - CHS
2 stops20h 35mMultiple Airlines
Deal found 1/15$505
This Alaska Airlines deal was found by Cheapflights users on 1/16. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/26:45 pmCHS - ORD
1 stop30h 14mAlaska Airlines
Sun 10/52:05 pmORD - CHS
2 stops26h 26mAlaska Airlines
Deal found 1/16$666
This Mytrip deal was found by Cheapflights users on 1/15. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/247:15 amCHS - RFD
3 stops27h 21mMultiple Airlines
Sun 1/265:00 pmRFD - CHS
3 stops26h 50mMultiple Airlines
Deal found 1/15$684

Find flights from Charleston to Chicago within your budget

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 January 16, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

CharlestonChicago

CHS - MDW

CHSMDW

Charleston

Wed 2/19

8:50 am-4:55 pm

1 stop9h 05m

Chicago Midway

Sun 2/23

4:20 pm-7:20 pm

Nonstop2h 00m

$335

CharlestonChicago

CHS - ORD

CHSORD

Charleston

Fri 2/21

5:25 pm-10:44 pm

1 stop6h 19m

Chicago O'Hare Intl

Mon 2/24

1:12 pm-4:18 pm

Nonstop2h 06m

$335

CharlestonChicago

CHS - ORD

CHSORD

Charleston

Tue 3/11

2:15 pm-9:44 am

2 stops20h 29m

Chicago O'Hare Intl

Sun 3/16

9:16 am-1:09 pm

3 stops26h 53m

$339

CharlestonChicago

CHS - ORD

CHSORD

Charleston

Sun 3/9

9:31 pm-9:28 am

1 stop12h 57m

Chicago O'Hare Intl

Thu 3/13

5:22 pm-10:57 pm

3 stops28h 35m

$343

CharlestonChicago

CHS - ORD

CHSORD

Charleston

Wed 2/19

11:30 am-9:30 pm

2 stops11h 00m

Chicago O'Hare Intl

Sat 2/22

7:00 am-9:55 pm

2 stops13h 55m

$344

CharlestonChicago

CHS - MDW

CHSMDW

Charleston

Fri 2/28

5:35 am-10:12 am

1 stop5h 37m

Chicago Midway

Mon 3/3

12:44 pm-6:00 pm

1 stop4h 16m

$345

CharlestonChicago

CHS - ORD

CHSORD

Charleston

Sun 3/2

5:35 am-8:30 am

1 stop3h 55m

Chicago O'Hare Intl

Mon 3/3

6:45 am-12:25 pm

1 stop4h 40m

$345

CharlestonChicago

CHS - ORD

CHSORD

Charleston

Thu 3/13

6:20 am-7:57 am

Nonstop2h 37m

Chicago O'Hare Intl

Sun 3/16

7:10 am-10:24 am

Nonstop2h 14m

$349

CharlestonChicago

CHS - MDW

CHSMDW

Charleston

Sun 3/2

7:10 am-5:30 pm

2 stops11h 20m

Chicago Midway

Sun 3/9

6:26 pm-4:01 pm

2 stops20h 35m

$505

CharlestonChicago

CHS - ORD

CHSORD

Charleston

Wed 3/5

10:48 am-4:27 pm

1 stop6h 39m

$69

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/16

Showing 1-10 of 23 results
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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 January.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
FareScanPrice Accuracy3 starsTrust Score*1 star
CheapOairPrice Accuracy2 starsTrust Score*2 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.

Travel insights for flights from Charleston to Chicago

Get recent, data-driven insights about flights from Charleston to Chicago including ideal travel times, pricing trends, and more.

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 January 10, 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 $320). 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 January 16, 2025.

Unlike in the afternoon, when flights are generally more expensive, you can save up to 24% on flights from Charleston to Chicago by exploring options for tickets at noon.

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 January 16, 2025.

The most flights from CHS to CHI are scheduled on a Monday (14 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (4 on average).

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

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.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

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).

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 January 16, 2025.
Read reviews from past customers who have flown Spirit Airlines, United Airlines and Southwest from Charleston to Chicago. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,659 reviews

Boarding

8.2

Food

7.2

Overall

8.1

Entertainment

7.7

Comfort

8.1

Crew

8.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Southwest
8.1
Very good
4,659 reviews
Southwest
8.1
Very good
4,659 reviews

Boarding

8.2

Food

7.2

Overall

8.1

Entertainment

7.7

Comfort

8.1

Crew

8.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Delta
8.0
Very good
8,511 reviews
Southwest
8.1
Very good
4,659 reviews

Boarding

8.2

Food

7.2

Overall

8.1

Entertainment

7.7

Comfort

8.1

Crew

8.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

JetBlue
7.4
Good
3,199 reviews
Southwest
8.1
Very good
4,659 reviews

Boarding

8.2

Food

7.2

Overall

8.1

Entertainment

7.7

Comfort

8.1

Crew

8.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

United Airlines
7.4
Good
8,965 reviews
Southwest
8.1
Very good
4,659 reviews

Boarding

8.2

Food

7.2

Overall

8.1

Entertainment

7.7

Comfort

8.1

Crew

8.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Allegiant Air
7.4
Good
801 reviews
Southwest
8.1
Very good
4,659 reviews

Boarding

8.2

Food

7.2

Overall

8.1

Entertainment

7.7

Comfort

8.1

Crew

8.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

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 10 outbound flights to Chicago per day. 5 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 $335 on this airline. Additional options worth looking into are American Airlines and Spirit Airlines, starting at $335 and $339 round-trip. You may be able to fly from Charleston to Chicago for 5% 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 ($69), JetBlue ($93), and Delta ($137).

  • 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 American Airlines (84%), Qatar Airways (84%) and Alaska Airlines (84%).

  • What are the cheapest flights from Charleston to Chicago?

    On average you can expect to pay $831 for a flight from Charleston to Chicago. The cheapest flight overall is $174 while the most popular route, (Charleston - Chicago O'Hare Intl) is currently priced at $151.

  • 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 $320). 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
New Buffalo
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

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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 5 airlines flying from Charleston to Chicago

Discover the top 5 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 January 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$81Average$163FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$207Average$385FlexibilityNo cancel feeOn-time69%
DeltaCheapest$230Average$407FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$242Average$348FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$325Average$485FlexibilityNo cancel feeOn-time63%
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