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Flights from San Juan to Chicago from $79

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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