S$231 Cheap Flights from Chicago to San Juan

View S$231 flight on Fri, 17 Oct, 2025Opens in a new window

Popular airlines from Chicago O'Hare Intl. Airport (ORD) to Luis Munoz Marin Intl. Airport (SJU)

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Cheap Flights from Chicago to San Juan (ORD-SJU)

Prices were available within the past 7 days and start at S$231 for one-way flights and S$496 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Mon, 20 Oct - Tue, 21 Oct
ORD
Chicago
SJU
San Juan
S$496 Return, found 6 days ago
S$496
Return
found 6 days ago
Select Delta flight, departing Mon, 20 Oct from Chicago to San Juan, returning Tue, 21 Oct, priced at S$496 found 6 days ago
JetBlue Airways
Wed, 25 Feb - Fri, 6 Mar
ORD
Chicago
SJU
San Juan
S$498 Return, found 1 day ago
S$498
Return
found 1 day ago
Select JetBlue Airways flight, departing Wed, 25 Feb from Chicago to San Juan, returning Fri, 6 Mar, priced at S$498 found 1 day ago
Delta
Mon, 20 Oct - Tue, 21 Oct
ORD
Chicago
SJU
San Juan
S$503 Return, found 6 days ago
S$503
Return
found 6 days ago
Select Delta flight, departing Mon, 20 Oct from Chicago to San Juan, returning Tue, 21 Oct, priced at S$503 found 6 days ago
Delta
Mon, 5 Jan - Fri, 9 Jan
ORD
Chicago
SJU
San Juan
S$504 Return, found 8 hours ago
S$504
Return
found 8 hours ago
Select Delta flight, departing Mon, 5 Jan from Chicago to San Juan, returning Fri, 9 Jan, priced at S$504 found 8 hours ago
Delta
Wed, 25 Feb - Tue, 10 Mar
ORD
Chicago
SJU
San Juan
S$516 Return, found 1 day ago
S$516
Return
found 1 day ago
Select Delta flight, departing Wed, 25 Feb from Chicago to San Juan, returning Tue, 10 Mar, priced at S$516 found 1 day ago
Delta
Mon, 20 Oct - Tue, 21 Oct
ORD
Chicago
SJU
San Juan
S$519 Return, found 6 days ago
S$519
Return
found 6 days ago
Select Delta flight, departing Mon, 20 Oct from Chicago to San Juan, returning Tue, 21 Oct, priced at S$519 found 6 days ago
Delta
Mon, 20 Oct - Tue, 21 Oct
ORD
Chicago
SJU
San Juan
S$529 Return, found 6 days ago
S$529
Return
found 6 days ago
Select Delta flight, departing Mon, 20 Oct from Chicago to San Juan, returning Tue, 21 Oct, priced at S$529 found 6 days ago
Delta
Tue, 16 Dec - Thu, 18 Dec
ORD
Chicago
SJU
San Juan
S$536 Return, found 2 days ago
S$536
Return
found 2 days ago
Select Delta flight, departing Tue, 16 Dec from Chicago to San Juan, returning Thu, 18 Dec, priced at S$536 found 2 days ago
United
Sun, 4 Jan - Fri, 9 Jan
ORD
Chicago
SJU
San Juan
S$562 Return, found 1 day ago
S$562
Return
found 1 day ago
Select United flight, departing Sun, 4 Jan from Chicago to San Juan, returning Fri, 9 Jan, priced at S$562 found 1 day ago
American Airlines
Sun, 4 Jan - Fri, 9 Jan
ORD
Chicago
SJU
San Juan
S$575 Return, found 1 day ago
S$575
Return
found 1 day ago
Select American Airlines flight, departing Sun, 4 Jan from Chicago to San Juan, returning Fri, 9 Jan, priced at S$575 found 1 day ago

Find the cheapest month to fly from Chicago (ORD) to San Juan (SJU)

January is typically the cheapest month to fly

From S$152 - S$494 per traveller.

Graph displaying average flight prices per month

Chicago to San Juan route information
Origin airport
O'Hare Intl.
Destination airport
Luis Munoz Marin Intl.
Airlines serving
American Airlines, Delta, United
Return price
S$496
Distance
3317 km
Average flight time
5 hours 47 mins

Perfect flights from Chicago to San Juan

Your Journey from Chicago to San Juan

Start your unforgettable journey with Expedia. Our broad selection of flights from Chicago to San Juan caters to every travel need. Whether you're yearning for a romantic escape, a solo adventure, or a cultural immersion, we've got you covered.
 

Choosing Your Ideal Flight

With Expedia, you have access to a wide range of airlines, including Delta, United, American Airlines, JetBlue Airways. Our selection of flights from O'Hare Intl. to Luis Munoz Marin Intl. caters to every traveler's requirements, ensuring your journey aligns with your schedule. With options from 20 airlines, you're bound to find the perfect flight.
 

Maximizing Value with Chicago to San Juan Flights

Experience the joy of finding cheap flights from O'Hare Intl. to Luis Munoz Marin Intl. that fit your budget. Keep an eye out for our special deals and discounts, and check our flexible one-way fares from S$231 and roundtrip prices from S$496*.
 

Pre-Flight Essentials

Ensure a smooth journey from Chicago to San Juan with Expedia. From information about check-in times and in-flight amenities to guidance on baggage policies, we provide all the essentials to prepare you for your flight.
 

Experience the Vibrant San Juan

Picture yourself stepping off the plane in San Juan and immersing yourself in the unique atmosphere of San Juan. From local markets to cultural festivals, each city offers its distinct charm. Make the most of your trip by exploring local attractions and indulging in the local cuisine. With Expedia, explore all this and more, tailored to your budget.
 

Added Convenience on Your Chicago to San Juan Flight

Traveling with Expedia is more than just a flight. We offer details about in-flight amenities, baggage policies, and more to ensure a smooth and hassle-free journey. Choose from our variety of airlines and embark on a memorable journey from Chicago to San Juan.
 

Beyond the Flight – Exploring San Juan

With Expedia, your adventure extends beyond the flight. Explore San Juan at your own pace by renting a car or booking a hotel. Discover hidden gems off the beaten path and create unforgettable memories.
 

Book Your Flight from Chicago to San Juan with Confidence

Planning your next great adventure is a breeze with Expedia. Our user-friendly platform, unbeatable prices, and round-the-clock customer support make your travel experience seamless and stress-free. Embark on your journey from Chicago to San Juan with confidence. Book your travel arrangements with Expedia today.
 
*Note: Prices may vary based on availability and are subject to change.

Frequently asked questions

How much is a flight from ORD to Luis Munoz Marin Intl. Airport (SJU)?
Round-trip journeys from O'Hare Intl. Airport (ORD) to Isla Verde Intl. Airport start from S$496. This price is based on fares listed within the last 7 days on Expedia for flights departing within the next year — book now to avoid missing out. Prices and availability are subject to change. Additional terms apply.
Do I need to pay a cancellation fee if I cancel my flight from O'Hare Intl. Airport (ORD) to Luis Munoz Marin Intl. Airport (SJU)?
The majority of flights can be cancelled online, but each air carrier has its own set of terms and conditions. If you do need to cancel your flight, check out our Customer Service Portal and follow the instructions.
How do I find cheap flights from O'Hare Intl. Airport (ORD) to SJU that have flexible change policies?
Many airlines offer the option to reschedule your flight without a change fee. All you pay is the difference between the original flight and the new flight. When you're searching for O'Hare Airport to Luis Munoz Marin Intl. Airport (SJU) flights, you'll see a "no change fees" filter for you to select.
How far is the flight from O'Hare Intl. Airport (ORD) to Luis Munoz Marin Intl. Airport (SJU)?
The flight distance between O'Hare Intl. Airport (ORD) and Luis Munoz Marin Intl. Airport (SJU) is 3,300 kilometres. Bring along a drink, a snack and a good movie. Keep yourself busy in the air and the hours will zip by.
Which airlines fly direct from O'Hare Airport to Luis Munoz Marin Intl. Airport (SJU)?
United Airlines (UA) is a popular choice. It operates 30 flights between O'Hare Airport and Luis Munoz Marin Intl. Airport (SJU) each month. If you're eager for more options, check out the ticket prices from American Airlines (AA). This carrier operates 21 flights every month between these airports.
Are O'Hare Airport to SJU flight tickets cheaper when they're purchased at the last minute?
Last-minute planners can occasionally nab a bargain, with some super cheap airfares from O'Hare Airport to SJU popping up a few weeks before the departure date. If you'd rather book ahead of time, Expedia compares and updates all the best flight deals continuously — as early as 12 months in advance in some cases. It depends on the carrier though, as not every airline advertises prices so far in advance.

Explore a world of travel with Expedia

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