Book your flight from Charleston (CHS) to Chicago (MDW) at the best prices. Fares start from $379.
Charleston
CHS
→
Chicago
MDW
11/04/2025 – 11/11/2025
Cheap flight deals from Charleston to Chicago
Average price start from:
i
$325
Round-trip flights from Charleston to Chicago starting at $325. Book now for the best deals!
One-way from:
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$143
One-way flights from Charleston to Chicago starting at $143. Great for flexible travel!
Cheapest day:
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Wednesday
Wednesday is the cheapest day to fly from Charleston to Chicago. Save more by booking on this day!
Cheapest In:
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$74
Apr 2025
Apr 2025 is the cheapest month to fly from Charleston to Chicago with prices starting at $74.
Find flight deals from Charleston to Chicago
Cheapest flights from Charleston to Chicago
ONEWAY FLIGHTS
LAST MINUTE
CHEAP FLIGHTS
BEST FLIGHTS
Explore the cheapest oneway flights from Charleston to Chicago spotted daily.
CHS
Charleston
CHS - Charleston • 2025-11-04 • 09:00
Unknown
60 min
MDW
Unknown City
$143
Non-stop • 60 min
CHS
Charleston
CHS - Charleston • 2025-11-04 • 09:00
Unknown
60 min
MDW
Unknown City
$146
Non-stop • 60 min
CHS
Charleston
CHS - Charleston • 2025-11-04 • 09:00
Unknown
60 min
MDW
Unknown City
$153
Non-stop • 60 min
CHS
Charleston
CHS - Charleston • 2025-11-04 • 09:00
Unknown
60 min
MDW
Unknown City
$160
Non-stop • 60 min
CHS
Charleston
CHS - Charleston • 2025-11-04 • 09:00
Unknown
60 min
MDW
Unknown City
$231
Non-stop • 60 min
Price Trends & Analysis
Monthly Price Trends
The cheapest month for flights from Charleston to Chicago is September.
Weather & Climate Information
Temperature
Chicago experiences a humid continental climate with cold winters, where temperatures can drop below freezing, and hot summers with average highs around 85°F (29°C). The best times for comfortable travel are late spring (May) and early fall (September to October), when temperatures are mild and outdoor activities are most enjoyable.
Rainfall
The best time to visit Chicago is from late spring to early autumn (May to September), when the weather is warm and pleasant for outdoor activities. This period also coincides with vibrant local events like the Chicago Blues Festival and the Chicago Air and Water Show, enhancing your experience in the city.
Airlines at MDW
Discover excellent flight options from Charleston to Chicago with top airlines including Southwest Airlines, Delta Air Lines, Frontier Airlines, Allegiant Air. These carriers offer reliable service and comfortable connections between these popular destinations.
The average flight time is approximately 10-15 hours, with most routes featuring one stopover for optimal pricing and convenience. When planning your journey from Charleston to Chicago, these airlines provide excellent connectivity and modern aircraft for a pleasant travel experience.
Places to Visit in Chicago
Chicago, the Windy City, dazzles with its stunning skyline and vibrant neighborhoods, each offering a unique blend of culture and history. Visitors can immerse themselves in world-class museums like the Art Institute, savor deep-dish pizza, and stroll along the iconic Lake Michigan shoreline. With its rich jazz and blues heritage, bustling food scene, and architectural marvels like the Willis Tower, Chicago promises an unforgettable adventure that captivates both the senses and the soul.
About Chicago
Explore the wonders of Chicago on your journey from Charleston. This remarkable destination blends cultural treasures with modern amenities, creating an enriching travel experience. Consider visiting during off-peak seasons for better value and fewer crowds.
Airlines Flying from Charleston to Chicago
Discover excellent flight options from Charleston to Chicago with top airlines including Southwest Airlines, Delta Air Lines, Frontier Airlines, Allegiant Air. These carriers offer reliable service and comfortable connections between these popular destinations.
The average flight time is approximately 10-15 hours, with most routes featuring one stopover for optimal pricing and convenience. When planning your journey from Charleston to Chicago, these airlines provide excellent connectivity and modern aircraft for a pleasant travel experience.
Hotels in Chicago
Explore excellent hotel options near MDW Airport for your Chicago visit. These hotels near Chicago airport combine convenience with comfort, making them perfect for both short layovers and extended stays. Check for special offers and airport shuttle services.
Hotel
Category: Standard
Comfortable accommodations with modern amenities.
Location: Near airport
Hotel ID:
About Chicago
Explore the wonders of Chicago on your journey from Charleston. This remarkable destination blends cultural treasures with modern amenities, creating an enriching travel experience. Consider visiting during off-peak seasons for better value and fewer crowds.
Places to Visit in Chicago
Chicago, the Windy City, dazzles with its stunning skyline and vibrant neighborhoods, each offering a unique blend of culture and history. Visitors can immerse themselves in world-class museums like the Art Institute, savor deep-dish pizza, and stroll along the iconic Lake Michigan shoreline. With its rich jazz and blues heritage, bustling food scene, and architectural marvels like the Willis Tower, Chicago promises an unforgettable adventure that captivates both the senses and the soul.
Hotels in Chicago
Explore excellent hotel options near MDW Airport for your Chicago visit. These hotels near Chicago airport combine convenience with comfort, making them perfect for both short layovers and extended stays. Check for special offers and airport shuttle services.
Hotel
Category: Standard
Comfortable accommodations with modern amenities.
Location: Near airport
Hotel ID:
Airlines Flying from Charleston to Chicago
Discover excellent flight options from Charleston to Chicago with top airlines including Southwest Airlines, Delta Air Lines, Frontier Airlines, Allegiant Air. These carriers offer reliable service and comfortable connections between these popular destinations.
The average flight time is approximately 10-15 hours, with most routes featuring one stopover for optimal pricing and convenience. When planning your journey from Charleston to Chicago, these airlines provide excellent connectivity and modern aircraft for a pleasant travel experience.
Frequently Asked Questions
What's the best deal for flights from Charleston to Chicago?
The lowest fare available is $143. Maximize savings by booking during September and selecting Wednesday flights.
How many hours does it take to fly from Charleston to Chicago?
Flight duration typically ranges around 10-15 hours, with most flights including one stopover for optimal route efficiency.
Which carriers fly between Charleston and Chicago?
Major airlines serving this route include Southwest Airlines, Delta Air Lines, Frontier Airlines. Each offers different schedules and amenities to suit various travel preferences.
What's the ideal booking window for this route?
Book 2-3 months in advance for the best prices. Traveling during September can provide additional savings opportunities.
Are there convenient hotels near MDW Airport?
Yes, MDW Airport is surrounded by hotels offering shuttle services and modern amenities for travelers.
Why should I visit Chicago?
Chicago offers an incredible mix of cultural experiences and modern attractions. Plan your visit during pleasant weather months for the most enjoyable experience.
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