Discover affordable flights from San Juan to Chicago with prices starting from $303. Book your journey today!
San Juan
SJU
→
Chicago
ORD
10/22/2025 – 10/29/2025
Cheap flight deals from San Juan to Chicago
Average price start from:
i
$130
Round-trip flights from San Juan to Chicago starting at $130. Book now for the best deals!
One-way from:
i
$79
One-way flights from San Juan to Chicago starting at $79. Great for flexible travel!
Cheapest day:
i
Tuesday
Tuesday is the cheapest day to fly from San Juan to Chicago. Save more by booking on this day!
Cheapest In:
i
$146
Feb 2025
Feb 2025 is the cheapest month to fly from San Juan to Chicago with prices starting at $146.
Find flight deals from San Juan to Chicago
Cheapest flights from San Juan to Chicago
ONEWAY FLIGHTS
LAST MINUTE
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BEST FLIGHTS
Explore the cheapest oneway flights from San Juan to Chicago spotted daily.
SJU
San Juan
SJU - San Juan • 2025-10-22 • 09:00
Unknown
60 min
ORD
Unknown City
$79
Non-stop • 60 min
SJU
San Juan
SJU - San Juan • 2025-10-22 • 09:00
Unknown
60 min
ORD
Unknown City
$81
Non-stop • 60 min
SJU
San Juan
SJU - San Juan • 2025-10-22 • 09:00
Unknown
60 min
MKE
Unknown City
$84
Non-stop • 60 min
SJU
San Juan
SJU - San Juan • 2025-10-22 • 09:00
Unknown
60 min
MSN
Unknown City
$111
Non-stop • 60 min
SJU
San Juan
SJU - San Juan • 2025-10-22 • 09:00
Unknown
60 min
ORD
Unknown City
$118
Non-stop • 60 min
SJU
San Juan
SJU - San Juan • 2025-10-22 • 09:00
Unknown
60 min
MKE
Unknown City
$127
Non-stop • 60 min
SJU
San Juan
SJU - San Juan • 2025-10-22 • 09:00
Unknown
60 min
MKE
Unknown City
$138
Non-stop • 60 min
SJU
San Juan
SJU - San Juan • 2025-10-22 • 09:00
Unknown
60 min
MSP
Unknown City
$157
Non-stop • 60 min
SJU
San Juan
SJU - San Juan • 2025-10-22 • 09:00
Unknown
60 min
ORD
Unknown City
$158
Non-stop • 60 min
SJU
San Juan
SJU - San Juan • 2025-10-22 • 09:00
Unknown
60 min
MSP
Unknown City
$165
Non-stop • 60 min
SJU
San Juan
SJU - San Juan • 2025-10-22 • 09:00
Unknown
60 min
MSP
Unknown City
$168
Non-stop • 60 min
SJU
San Juan
SJU - San Juan • 2025-10-22 • 09:00
Unknown
60 min
MSP
Unknown City
$173
Non-stop • 60 min
Price Trends & Analysis
Monthly Price Trends
Lowest fares from San Juan to Chicago typically available in February.
Weather & Climate Information
Temperature
Chicago experiences a continental climate with cold winters, where temperatures can drop to the teens Fahrenheit, and warm summers, often reaching the 80s and 90s. The best times for comfortable travel are late spring (May) and early fall (September to October), when temperatures are mild and pleasant, averaging between 60°F and 75°F.
Rainfall
The best time to visit Chicago is from late spring to early fall (May to September), when the weather is warm and perfect for outdoor activities. This period also features vibrant local events like the Chicago Blues Festival and Lollapalooza, making it an ideal time to experience the city's culture and lively atmosphere.
Airlines at Chicago
Discover excellent flight options from San Juan to Chicago with top airlines including Frontier Airlines, Spirit Airlines, American Airlines, United Airlines. 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 San Juan to Chicago, these airlines provide excellent connectivity and modern aircraft for a pleasant travel experience.
Places to Visit in Chicago
Chicago, the Windy City, enchants with its stunning skyline and vibrant cultural tapestry, where world-class museums meet spirited jazz clubs. Stroll along the iconic Magnificent Mile, indulge in deep-dish pizza, and explore the rich history at the Art Institute and the historic Chicago Riverwalk. Visitors can expect a dynamic blend of art, architecture, and culinary delights that invite exploration and celebration, making every moment in this urban gem unforgettable.
About Chicago
Embark on an exciting adventure from San Juan to Chicago and discover a world of possibilities. This dynamic city offers a perfect mix of traditional charm and contemporary attractions. Time your visit during off-peak periods for maximum savings and comfort.
Airlines Flying from San Juan to Chicago
Discover excellent flight options from San Juan to Chicago with top airlines including Frontier Airlines, Spirit Airlines, American Airlines, United Airlines. 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 San Juan to Chicago, these airlines provide excellent connectivity and modern aircraft for a pleasant travel experience.
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
Embark on an exciting adventure from San Juan to Chicago and discover a world of possibilities. This dynamic city offers a perfect mix of traditional charm and contemporary attractions. Time your visit during off-peak periods for maximum savings and comfort.
Places to Visit in Chicago
Chicago, the Windy City, enchants with its stunning skyline and vibrant cultural tapestry, where world-class museums meet spirited jazz clubs. Stroll along the iconic Magnificent Mile, indulge in deep-dish pizza, and explore the rich history at the Art Institute and the historic Chicago Riverwalk. Visitors can expect a dynamic blend of art, architecture, and culinary delights that invite exploration and celebration, making every moment in this urban gem unforgettable.
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 Juan to Chicago
Discover excellent flight options from San Juan to Chicago with top airlines including Frontier Airlines, Spirit Airlines, American Airlines, United Airlines. 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 San Juan 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 San Juan to Chicago?
The lowest fare available is $79. Maximize savings by booking during February and selecting Tuesday flights.
How many hours does it take to fly from San Juan to Chicago?
Flight duration typically ranges around 10-15 hours, with most flights including one stopover for optimal route efficiency.
Which carriers fly between San Juan and Chicago?
Major airlines serving this route include Frontier Airlines, Spirit Airlines, American 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 February can provide additional savings opportunities.
Are there convenient hotels near ORD Airport?
Yes, ORD 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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