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$91+ Cheap flights from Charleston (CHS) to Chicago (CHI)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 8/27. Fares are subject to change and may not be available on all flights or dates of travel.
CHS — CHI
ago 3 — ago 101
dom 8/3
dom 8/10
1 adult, Economy
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Cheapflights Tip: The best prices from Charleston to Chicago are usually found in September or August, booked 65 days in advance, depart on a Friday or Thursday and return on a Tuesday

Cheap flight deals from Charleston to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Charleston (CHS) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated julho 29, 2025.

Round-trip from

$181
(Southwest)

One-way from

$91
(Southwest)

Popular in

December

Cheapest in

September

Average price

$344

Good round-trip deal

$202 or less

Good one-way deal

$184 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. 7% potential increase in price ($28 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
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Average for round-trip flights in July 2025
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Price to beat on a round-trip flight from Charleston to Chicago (CHI).
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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 julho 29, 2025.

This Southwest deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
qua 8/276:35 amCHS - MDW
Nonstop2h 05mSouthwest
qua 9/36:05 pmMDW - CHS
Nonstop2h 10mSouthwest
Deal found 7/28$181
This American Airlines deal was found by Cheapflights users on 7/26. 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.
qua 10/16:16 pmCHS - ORD
Nonstop2h 33mAmerican Airlines
sáb 10/48:07 amORD - CHS
Nonstop2h 23mAmerican Airlines
Deal found 7/26$181
This Delta deal was found by Cheapflights users on 7/27. 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.
qua 8/277:10 amCHS - MDW
1 stop6h 18mDelta
sáb 8/306:17 pmMDW - CHS
1 stop4h 38mDelta
Deal found 7/27$201
This Delta deal was found by Cheapflights users on 7/27. 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.
qua 10/17:10 amCHS - ORD
1 stop4h 09mDelta
sáb 10/43:45 pmORD - CHS
1 stop4h 37mDelta
Deal found 7/27$201
This United Airlines deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sex 9/265:50 pmCHS - ORD
1 stop6h 40mUnited Airlines
seg 9/294:50 pmORD - CHS
Nonstop2h 18mUnited Airlines
Deal found 7/29$211
This Mytrip deal was found by Cheapflights users on 7/28. 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.
qui 10/212:10 pmCHS - ORD
1 stop11h 38mSpirit Airlines
dom 10/58:56 pmORD - CHS
2 stops19h 12mSpirit Airlines
Deal found 7/28$227
This JetBlue deal was found by Cheapflights users on 7/28. 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.
qua 12/1010:40 amCHS - ORD
1 stop9h 25mJetBlue
dom 12/147:00 amORD - CHS
1 stop5h 17mJetBlue
Deal found 7/28$230
This Southwest deal was found by Cheapflights users on 7/29. 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.
ter 8/268:35 amCHS - ORD
2 stops10h 20mSouthwest
sáb 8/307:30 amORD - CHS
1 stop8h 35mSouthwest
Deal found 7/29$236
This Orbitz deal was found by Cheapflights users on 7/27. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sex 8/159:05 amCHS - ORD
1 stop11h 22mMultiple Airlines
seg 8/1810:26 amORD - CHS
1 stop7h 46mMultiple Airlines
Deal found 7/27$269

Cheapflights Fare Finder

 
Customize your flight search to find flights from Charleston to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated julho 29, 2025.
Use the filters below to find and compare flights from Charleston to Chicago that are best for you.

Fly from

Charleston

Fly to

Chicago

Route

Depart

Return

Price

CharlestonChicago

CHS - MDW

CHSMDW

Charleston

qua 8/27

6:35 am-7:40 am

Nonstop2h 05m

Chicago Midway

qua 9/3

6:05 pm-9:15 pm

Nonstop2h 10m

$181

CharlestonChicago

CHS - ORD

CHSORD

Charleston

qua 10/1

6:16 pm-7:49 pm

Nonstop2h 33m

Chicago O'Hare Intl

sáb 10/4

8:07 am-11:30 am

Nonstop2h 23m

$181

CharlestonChicago

CHS - MDW

CHSMDW

Charleston

qua 8/27

7:10 am-12:28 pm

1 stop6h 18m

Chicago Midway

sáb 8/30

6:17 pm-11:55 pm

1 stop4h 38m

$201

CharlestonChicago

CHS - ORD

CHSORD

Charleston

qua 10/1

7:10 am-10:19 am

1 stop4h 09m

Chicago O'Hare Intl

sáb 10/4

3:45 pm-9:22 pm

1 stop4h 37m

$201

CharlestonChicago

CHS - ORD

CHSORD

Charleston

sex 9/26

5:50 pm-11:30 pm

1 stop6h 40m

Chicago O'Hare Intl

dom 9/28

7:10 am-10:35 am

Nonstop2h 25m

$211

CharlestonChicago

CHS - ORD

CHSORD

Charleston

qui 10/2

12:10 pm-10:48 pm

1 stop11h 38m

Chicago O'Hare Intl

dom 10/5

8:56 pm-5:08 pm

2 stops19h 12m

$227

CharlestonChicago

CHS - ORD

CHSORD

Charleston

qua 12/10

10:40 am-7:05 pm

1 stop9h 25m

Chicago O'Hare Intl

dom 12/14

7:00 am-1:17 pm

1 stop5h 17m

$230

CharlestonChicago

CHS - ORD

CHSORD

Charleston

ter 8/26

8:35 am-5:55 pm

2 stops10h 20m

Chicago O'Hare Intl

sáb 8/30

7:30 am-5:05 pm

1 stop8h 35m

$236

CharlestonChicago

CHS - ORD

CHSORD

Charleston

sex 8/15

9:05 am-7:27 pm

1 stop11h 22m

Chicago O'Hare Intl

seg 8/18

10:26 am-7:12 pm

1 stop7h 46m

$269

CharlestonChicago

CHS - MDW

CHSMDW

Charleston

qua 8/27

6:35 am-7:40 am

Nonstop2h 05m

$91

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/28

Showing 1-10 of 21 results
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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 July 25, 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 65 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

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

Currently, August is the cheapest month in which you can book a flight from Charleston to Chicago (average of $245). Flying from Charleston to Chicago in March is currently the most expensive (average of $321). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from CHS to CHI?

Find hourly flight availability from Charleston to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated julho 29, 2025.

Unlike in the afternoon, when flights are generally more expensive, you can save up to 30% 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 July 27, 2025.

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

Weekly flight availability from Charleston to Chicago

Explore weekly flight availability from Charleston to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated julho 29, 2025.

The most flights from CHS to CHI are scheduled on a Monday (19 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (5 on average).

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated julho 29, 2025.
See what other customers who have flown with Southwest, Delta, and United Airlines from Charleston to Chicago have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,238 reviews

Overall

8.0

Boarding

8.1

Comfort

8.0

Food

7.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Southwest
8.0
Very good
4,238 reviews
Southwest
8.0
Very good
4,238 reviews

Overall

8.0

Boarding

8.1

Comfort

8.0

Food

7.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Delta
8.0
Very good
7,977 reviews
Southwest
8.0
Very good
4,238 reviews

Overall

8.0

Boarding

8.1

Comfort

8.0

Food

7.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
United Airlines
7.4
Good
8,899 reviews
Southwest
8.0
Very good
4,238 reviews

Overall

8.0

Boarding

8.1

Comfort

8.0

Food

7.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
JetBlue
7.3
Good
2,913 reviews
Southwest
8.0
Very good
4,238 reviews

Overall

8.0

Boarding

8.1

Comfort

8.0

Food

7.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,238 reviews

Overall

8.0

Boarding

8.1

Comfort

8.0

Food

7.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.

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 14 outbound flights to Chicago per day. 3 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 $181 on this airline. Additional options worth looking into are American Airlines and Delta, starting at $181 and $201 round-trip. You may be able to fly from Charleston to Chicago for 50% less than the average price by searching for these airlines.

  • What are the cheapest airlines to fly from Charleston to Chicago one-way?

    The cheapest airlines for a one-way flight from Charleston to Chicago are Southwest ($91), United Airlines ($91), and Spirit Airlines ($94).

  • 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 (91%), Alaska Airlines (87%) and Qatar Airways (84%).

  • What are the cheapest flights from Charleston to Chicago?

    On average you can expect to pay $1,997 for a flight from Charleston to Chicago. The cheapest flight overall is $90 while the most popular route, (Charleston - Chicago O'Hare Intl) is currently priced at $192.

  • 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 Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
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 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 julho 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$135Average$350FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$224Average$387FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$254Average$417FlexibilityNo cancel feeOn-time69%

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