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$141+ 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 7/10. Fares are subject to change and may not be available on all flights or dates of travel.
CHS — CHI
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
1 adult, Economy
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Cheapflights Tip: The best prices from Charleston to Chicago are usually found in October or July, 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 June 12, 2025.

Round-trip from

$249
(American Airlines)

One-way from

$141
(Mytrip)

Popular in

December

Cheapest in

October

Average price

$372

Good round-trip deal

$310 or less

Good one-way deal

$174 or less
From Charleston to Chicago (CHI)
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One-way flight from Charleston to Chicago (CHI)
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Highest demand for flights based on searches. 5% potential increase in price ($20 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($5 potential savings vs. average RT price).
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Average for round-trip flights in June 2025
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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).
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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 June 12, 2025.

This American Airlines deal was found by Cheapflights users on 6/11. 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.
Thu 8/77:56 pmCHS - ORD
Nonstop2h 34mAmerican Airlines
Sun 8/109:55 amORD - CHS
Nonstop2h 22mAmerican Airlines
Deal found 6/11$249
This Mytrip deal was found by Cheapflights users on 6/12. 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.
Wed 6/257:03 amCHS - ORD
1 stop24h 34mSpirit Airlines
Fri 6/279:28 pmORD - CHS
1 stop24h 01mSpirit Airlines
Deal found 6/12$252
This United Airlines deal was found by Cheapflights users on 6/12. 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 9/610:08 amCHS - ORD
1 stop5h 21mUnited Airlines
Tue 9/97:14 amORD - CHS
Nonstop2h 25mUnited Airlines
Deal found 6/12$258
This Southwest deal was found by Cheapflights users on 6/10. 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 8/66:45 pmCHS - MDW
1 stop4h 40mSouthwest
Sun 8/109:00 pmMDW - CHS
Nonstop2h 05mSouthwest
Deal found 6/10$259
This Delta deal was found by Cheapflights users on 6/11. 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.
Mon 8/46:23 pmCHS - MDW
1 stop4h 19mDelta
Sat 8/96:00 amMDW - CHS
1 stop4h 48mDelta
Deal found 6/11$268
This Delta deal was found by Cheapflights users on 6/12. 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.
Thu 8/75:15 amCHS - ORD
1 stop5h 55mDelta
Mon 8/115:45 amORD - CHS
1 stop7h 05mDelta
Deal found 6/12$268
This Mytrip deal was found by Cheapflights users on 6/11. 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.
Thu 8/213:32 pmCHS - RFD
2 stops21h 14mMultiple Airlines
Sun 8/243:06 pmRFD - CHS
2 stops22h 34mMultiple Airlines
Deal found 6/11$275
This Southwest deal was found by Cheapflights users on 6/12. 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 8/76:10 amCHS - ORD
1 stop11h 15mSouthwest
Mon 8/117:30 amORD - CHS
2 stops9h 25mSouthwest
Deal found 6/12$279
This Gotogate deal was found by Cheapflights users on 6/11. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/183:41 pmCHS - MDW
1 stop16h 39mFrontier
Sun 9/218:15 amMDW - CHS
1 stop5h 21mFrontier
Deal found 6/11$311
This Mytrip deal was found by Cheapflights users on 6/10. 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.
Sat 7/268:56 amCHS - ORD
2 stops32h 45mMultiple Airlines
Fri 8/15:40 pmORD - CHS
1 stop26h 13mMultiple Airlines
Deal found 6/10$317
This Mytrip deal was found by Cheapflights users on 6/12. 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 6/247:03 amCHS - MDW
2 stops33h 34mMultiple Airlines
Fri 6/2710:34 amMDW - CHS
2 stops34h 55mMultiple Airlines
Deal found 6/12$373
This Frontier deal was found by Cheapflights users on 6/11. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/103:31 pmCHS - ORD
2 stops9h 39mFrontier
Sun 10/126:20 amORD - CHS
1 stop7h 16mFrontier
Deal found 6/11$403

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 June 12, 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 - ORD

CHSORD

Charleston

Thu 8/7

7:56 pm-9:30 pm

Nonstop2h 34m

Chicago O'Hare Intl

Sun 8/10

9:55 am-1:17 pm

Nonstop2h 22m

$249

CharlestonChicago

CHS - ORD

CHSORD

Charleston

Wed 6/25

7:03 am-6:37 am

1 stop24h 34m

Chicago O'Hare Intl

Fri 6/27

9:28 pm-10:29 pm

1 stop24h 01m

$252

CharlestonChicago

CHS - ORD

CHSORD

Charleston

Sat 9/6

10:08 am-2:29 pm

1 stop5h 21m

Chicago O'Hare Intl

Tue 9/9

7:14 am-10:39 am

Nonstop2h 25m

$258

CharlestonChicago

CHS - MDW

CHSMDW

Charleston

Wed 8/6

6:45 pm-10:25 pm

1 stop4h 40m

Chicago Midway

Sun 8/10

9:00 pm-12:05 am

Nonstop2h 05m

$259

CharlestonChicago

CHS - MDW

CHSMDW

Charleston

Mon 8/4

6:23 pm-9:42 pm

1 stop4h 19m

Chicago Midway

Sat 8/9

6:00 am-11:48 am

1 stop4h 48m

$268

CharlestonChicago

CHS - ORD

CHSORD

Charleston

Thu 8/7

5:15 am-10:10 am

1 stop5h 55m

Chicago O'Hare Intl

Mon 8/11

5:45 am-1:50 pm

1 stop7h 05m

$268

CharlestonChicago

CHS - RFD

CHSRFD

Charleston

Thu 8/21

3:32 pm-11:46 am

2 stops21h 14m

Chicago Greater Rockford

Sun 8/24

3:06 pm-2:40 pm

2 stops22h 34m

$275

CharlestonChicago

CHS - ORD

CHSORD

Charleston

Thu 8/7

6:10 am-4:25 pm

1 stop11h 15m

Chicago O'Hare Intl

Mon 8/11

7:30 am-5:55 pm

2 stops9h 25m

$279

CharlestonChicago

CHS - MDW

CHSMDW

Charleston

Thu 9/18

3:41 pm-7:20 am

1 stop16h 39m

Chicago Midway

Sun 9/21

8:15 am-2:36 pm

1 stop5h 21m

$311

CharlestonChicago

CHS - ORD

CHSORD

Charleston

Sat 7/26

8:56 am-4:41 pm

2 stops32h 45m

Chicago O'Hare Intl

Fri 8/1

5:40 pm-8:53 pm

1 stop26h 13m

$317

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/11

Showing 1-10 of 24 results
1
2
3

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.

Read more about United Airlinesby Harriet Baskas
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.

Read more about Southwestby Marisa Garcia
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 9, 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 June 12, 2025.

Unlike in the afternoon, when flights are generally more expensive, you can save up to 36% 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 8, 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. Monday 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

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 June 12, 2025.

The most flights from CHS to CHI are scheduled on a Thursday (22 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 June 12, 2025.
Read reviews from past customers who have flown Alaska Airlines, Southwest and Delta from Charleston to Chicago. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Comfort

7.8

Food

7.1

Overall

8.0

Entertainment

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Comfort

7.8

Food

7.1

Overall

8.0

Entertainment

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Southwest
8.0
Very good
4,287 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Comfort

7.8

Food

7.1

Overall

8.0

Entertainment

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Delta
8.0
Very good
7,950 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Comfort

7.8

Food

7.1

Overall

8.0

Entertainment

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
United Airlines
7.4
Good
8,790 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Comfort

7.8

Food

7.1

Overall

8.0

Entertainment

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Allegiant Air
7.3
Good
725 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Comfort

7.8

Food

7.1

Overall

8.0

Entertainment

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

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 15 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 American Airlines. Our recent data shows that you can find tickets from as low as $249 on this airline. Additional options worth looking into are Spirit Airlines and United Airlines, starting at $252 and $258 round-trip. You may be able to fly from Charleston to Chicago for 32% 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 ($141), Delta ($146), and Southwest ($148).

  • 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 ANA (89%), Air Canada (83%) and Air New Zealand (83%).

  • What are the cheapest flights from Charleston to Chicago?

    On average you can expect to pay $1,730 for a flight from Charleston to Chicago. The cheapest flight overall is $122 while the most popular route, (Charleston - Chicago O'Hare Intl) is currently priced at $157.

  • 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

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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 June 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$81Average$200FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$251Average$414FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$271Average$359FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$285Average$410FlexibilityNo cancel feeOn-time63%
DeltaCheapest$298Average$432FlexibilityNo cancel feeOn-timeN/A

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