Find cheap flight tickets from Chicago (MDW) to San Antonio (SAT). Cheapest fare starts from $433.
Chicago
MDW
→
San Antonio
SAT
10/14/2025 – 10/21/2025
Cheap flight deals from Chicago to San Antonio
Average price start from:
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$170
Round-trip flights from Chicago to San Antonio starting at $170. Book now for the best deals!
One-way from:
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$105
One-way flights from Chicago to San Antonio starting at $105. Great for flexible travel!
Cheapest day:
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Wednesday
Wednesday is the cheapest day to fly from Chicago to San Antonio. Save more by booking on this day!
Cheapest In:
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$120
Dec 2025
Dec 2025 is the cheapest month to fly from Chicago to San Antonio with prices starting at $120.
Find flight deals from Chicago to San Antonio
Cheapest flights from Chicago to San Antonio
ONEWAY FLIGHTS
LAST MINUTE
CHEAP FLIGHTS
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Explore the cheapest oneway flights from Chicago to San Antonio spotted daily.
MDW
Chicago
MDW - Chicago • 2025-10-14 • 09:00
Unknown
60 min
SAT
Unknown City
$105
Non-stop • 60 min
MDW
Chicago
MDW - Chicago • 2025-10-14 • 09:00
Unknown
60 min
SAT
Unknown City
$172
Non-stop • 60 min
MDW
Chicago
MDW - Chicago • 2025-10-14 • 09:00
Unknown
60 min
SAT
Unknown City
$174
Non-stop • 60 min
MDW
Chicago
MDW - Chicago • 2025-10-14 • 09:00
Unknown
60 min
SAT
Unknown City
$184
Non-stop • 60 min
Price Trends & Analysis
Weekly Price Trends
Optimal pricing available on Wednesday for flights to San Antonio.
Monthly Price Trends
The cheapest month for flights from Chicago to San Antonio is October.
Weather & Climate Information
Temperature
San Antonio experiences a humid subtropical climate, with summer temperatures often exceeding 90°F (32°C) and mild winters averaging around 40-60°F (4-16°C). The best times for comfortable travel are during the spring (March to May) and fall (September to November), when temperatures are generally mild and rainfall is less frequent.
Rainfall
The best time to visit San Antonio is in the spring (March to May) when temperatures are mild and pleasant for outdoor activities. Additionally, plan your trip around local events like Fiesta San Antonio in April to experience vibrant culture and festivities, while avoiding the hot summer crowds.
Airlines at SAT
Experience seamless travel from Chicago to San Antonio with trusted airlines like Frontier Airlines, Delta Air Lines, Southwest Airlines. These carriers ensure reliable connections and flexible scheduling options for travelers.
Flight duration typically ranges around 10-15 hours, with most routes including one stopover in major aviation hubs. For your trip from Chicago to San Antonio, these airlines offer modern amenities and professional service to make your journey comfortable and enjoyable.
Places to Visit in San Antonio
San Antonio, a vibrant tapestry of history and culture, invites travelers to stroll along the enchanting River Walk, where Spanish colonial architecture and lush landscapes create a picturesque backdrop. Dive into the city's rich heritage at the iconic Alamo, a symbol of Texas independence, and explore the lively markets of the Historic Market Square, brimming with artisan crafts and tantalizing cuisine. Visitors can savor mouthwatering Tex-Mex dishes, enjoy captivating performances at local theaters, and immerse themselves in the warm, welcoming spirit of this dynamic city, making every moment unforgettable.
About San Antonio
Travel to San Antonio from Chicago for an unforgettable experience. This vibrant destination offers a perfect blend of culture, history, and modern attractions. The best time to visit is during off-peak seasons for better deals and fewer crowds.
Airlines Flying from Chicago to San Antonio
Experience seamless travel from Chicago to San Antonio with trusted airlines like Frontier Airlines, Delta Air Lines, Southwest Airlines. These carriers ensure reliable connections and flexible scheduling options for travelers.
Flight duration typically ranges around 10-15 hours, with most routes including one stopover in major aviation hubs. For your trip from Chicago to San Antonio, these airlines offer modern amenities and professional service to make your journey comfortable and enjoyable.
Hotels in San Antonio
When staying in San Antonio, look for hotels with easy access to SAT Airport. Most properties provide shuttle services for seamless airport transfers.
About San Antonio
Travel to San Antonio from Chicago for an unforgettable experience. This vibrant destination offers a perfect blend of culture, history, and modern attractions. The best time to visit is during off-peak seasons for better deals and fewer crowds.
Places to Visit in San Antonio
San Antonio, a vibrant tapestry of history and culture, invites travelers to stroll along the enchanting River Walk, where Spanish colonial architecture and lush landscapes create a picturesque backdrop. Dive into the city's rich heritage at the iconic Alamo, a symbol of Texas independence, and explore the lively markets of the Historic Market Square, brimming with artisan crafts and tantalizing cuisine. Visitors can savor mouthwatering Tex-Mex dishes, enjoy captivating performances at local theaters, and immerse themselves in the warm, welcoming spirit of this dynamic city, making every moment unforgettable.
Hotels in San Antonio
When staying in San Antonio, look for hotels with easy access to SAT Airport. Most properties provide shuttle services for seamless airport transfers.
Airlines Flying from Chicago to San Antonio
Experience seamless travel from Chicago to San Antonio with trusted airlines like Frontier Airlines, Delta Air Lines, Southwest Airlines. These carriers ensure reliable connections and flexible scheduling options for travelers.
Flight duration typically ranges around 10-15 hours, with most routes including one stopover in major aviation hubs. For your trip from Chicago to San Antonio, these airlines offer modern amenities and professional service to make your journey comfortable and enjoyable.
Frequently Asked Questions
What is the cheapest flight from Chicago to San Antonio?
The cheapest fare is $105. For the best deals, consider booking during October and flying on Wednesday.
How long is the flight from Chicago to San Antonio?
Average flight time is around 10-15 hours, depending on layovers and the chosen route. Most flights include one stopover for optimal pricing.
Which airlines fly from Chicago to San Antonio?
Multiple airlines operate this route including Frontier Airlines, Delta Air Lines, Southwest Airlines. Check current schedules and availability for the best options.
What is the best time to book flights?
Booking 2–3 months in advance usually gives the best prices. Consider flying during October for additional savings.
Are there hotels near SAT Airport?
Yes, several hotels are conveniently located near SAT Airport, including options with shuttle services for easy airport access.
What should I know about San Antonio?
San Antonio offers a perfect blend of culture, history, and modern attractions. The best time to visit is during pleasant weather months for optimal experiences.
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