Discover affordable flights from San Jose to Chicago with prices starting from $453. Book your journey today!
San Jose
SJC
→
Chicago
ORD
10/14/2025 – 10/21/2025
Cheap flight deals from San Jose to Chicago
Average price start from:
i
$130
Round-trip flights from San Jose to Chicago starting at $130. Book now for the best deals!
One-way from:
i
$44
One-way flights from San Jose to Chicago starting at $44. Great for flexible travel!
Cheapest day:
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Thursday
Thursday is the cheapest day to fly from San Jose to Chicago. Save more by booking on this day!
Cheapest In:
i
$122
Jul 2025
Jul 2025 is the cheapest month to fly from San Jose to Chicago with prices starting at $122.
Find flight deals from San Jose to Chicago
Cheapest flights from San Jose to Chicago
ONEWAY FLIGHTS
LAST MINUTE
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Explore the cheapest oneway flights from San Jose to Chicago spotted daily.
SJC
San Jose
SJC - San Jose • 2025-10-14 • 09:00
Unknown
60 min
ORD
Unknown City
$44
Non-stop • 60 min
SJC
San Jose
SJC - San Jose • 2025-10-14 • 09:00
Unknown
60 min
MSP
Unknown City
$54
Non-stop • 60 min
SJC
San Jose
SJC - San Jose • 2025-10-14 • 09:00
Unknown
60 min
ORD
Unknown City
$65
Non-stop • 60 min
SJC
San Jose
SJC - San Jose • 2025-10-14 • 09:00
Unknown
60 min
MSP
Unknown City
$87
Non-stop • 60 min
SJC
San Jose
SJC - San Jose • 2025-10-14 • 09:00
Unknown
60 min
MSP
Unknown City
$104
Non-stop • 60 min
SJC
San Jose
SJC - San Jose • 2025-10-14 • 09:00
Unknown
60 min
MSN
Unknown City
$115
Non-stop • 60 min
SJC
San Jose
SJC - San Jose • 2025-10-14 • 09:00
Unknown
60 min
MSN
Unknown City
$120
Non-stop • 60 min
SJC
San Jose
SJC - San Jose • 2025-10-14 • 09:00
Unknown
60 min
MKE
Unknown City
$129
Non-stop • 60 min
SJC
San Jose
SJC - San Jose • 2025-10-14 • 09:00
Unknown
60 min
MSN
Unknown City
$134
Non-stop • 60 min
SJC
San Jose
SJC - San Jose • 2025-10-14 • 09:00
Unknown
60 min
MSP
Unknown City
$145
Non-stop • 60 min
SJC
San Jose
SJC - San Jose • 2025-10-14 • 09:00
Unknown
60 min
ORD
Unknown City
$158
Non-stop • 60 min
SJC
San Jose
SJC - San Jose • 2025-10-14 • 09:00
Unknown
60 min
MSP
Unknown City
$171
Non-stop • 60 min
Price Trends & Analysis
Monthly Price Trends
The cheapest month for flights from San Jose to Chicago is October.
Weather & Climate Information
Temperature
Chicago experiences a humid continental climate, with winter temperatures averaging between 20°F to 30°F (-6°C to -1°C) and summer highs around 80°F to 90°F (27°C to 32°C). The best times for comfortable travel are late spring (May) and early fall (September to October), when temperatures are mild and humidity is lower.
Rainfall
The best time to visit Chicago is during late spring (May to early June) when temperatures are mild and outdoor festivals abound. Fall (September to October) is also ideal, offering beautiful foliage and events like the Chicago Gourmet Festival, while avoiding the summer tourist crowds.
Airlines at Chicago
Book your journey from San Jose to Chicago with leading airlines including Frontier Airlines, Spirit Airlines, American Airlines, Delta Air Lines. These carriers provide excellent connectivity and multiple daily options for convenient travel.
The typical flight time is about 10-15 hours, with most flights featuring one stopover for better pricing and route optimization. When traveling from San Jose to Chicago, these airlines ensure a smooth and comfortable experience with their modern fleet and professional service.
Places to Visit in Chicago
Chicago, the Windy City, enchants visitors with its stunning skyline adorned by architectural masterpieces like the Willis Tower and the historic Tribune Building. Dive into the vibrant arts scene at the Art Institute, where masterpieces await, or savor the city’s famous deep-dish pizza in bustling neighborhoods filled with jazz and blues. As you stroll along the picturesque Lake Michigan shoreline, you’ll experience the perfect fusion of rich history, diverse culture, and an electric atmosphere that beckons you to explore every corner of this dynamic metropolis.
About Chicago
Explore the wonders of Chicago on your journey from San Jose. 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 San Jose to Chicago
Book your journey from San Jose to Chicago with leading airlines including Frontier Airlines, Spirit Airlines, American Airlines, Delta Air Lines. These carriers provide excellent connectivity and multiple daily options for convenient travel.
The typical flight time is about 10-15 hours, with most flights featuring one stopover for better pricing and route optimization. When traveling from San Jose to Chicago, these airlines ensure a smooth and comfortable experience with their modern fleet and professional service.
Hotels in Chicago
Accommodations near ORD Airport provide excellent connectivity for travelers visiting Chicago. Look for hotels with shuttle services and modern amenities.
About Chicago
Explore the wonders of Chicago on your journey from San Jose. 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, enchants visitors with its stunning skyline adorned by architectural masterpieces like the Willis Tower and the historic Tribune Building. Dive into the vibrant arts scene at the Art Institute, where masterpieces await, or savor the city’s famous deep-dish pizza in bustling neighborhoods filled with jazz and blues. As you stroll along the picturesque Lake Michigan shoreline, you’ll experience the perfect fusion of rich history, diverse culture, and an electric atmosphere that beckons you to explore every corner of this dynamic metropolis.
Hotels in Chicago
Accommodations near ORD Airport provide excellent connectivity for travelers visiting Chicago. Look for hotels with shuttle services and modern amenities.
Airlines Flying from San Jose to Chicago
Book your journey from San Jose to Chicago with leading airlines including Frontier Airlines, Spirit Airlines, American Airlines, Delta Air Lines. These carriers provide excellent connectivity and multiple daily options for convenient travel.
The typical flight time is about 10-15 hours, with most flights featuring one stopover for better pricing and route optimization. When traveling from San Jose to Chicago, these airlines ensure a smooth and comfortable experience with their modern fleet and professional service.
Frequently Asked Questions
What is the cheapest flight from San Jose to Chicago?
The cheapest fare is $44. For the best deals, consider booking during October and flying on Thursday.
How long is the flight from San Jose to Chicago?
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 San Jose to Chicago?
Multiple airlines operate this route including Frontier Airlines, Spirit Airlines, American 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 ORD Airport?
Yes, several hotels are conveniently located near ORD Airport, including options with shuttle services for easy airport access.
What should I know about Chicago?
Chicago 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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