S$231 Cheap Flights from San Juan to Chicago

View S$231 flight on Tue, 4 Nov, 2025Opens in a new window

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

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

Prices were available within the past 7 days and start at S$231 for one-way flights and S$460 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Tue, 7 Oct - Fri, 17 Oct
SJU
San Juan
ORD
Chicago
S$460 Return, found 1 day ago
S$460
Return
found 1 day ago
Select Delta flight, departing Tue, 7 Oct from San Juan to Chicago, returning Fri, 17 Oct, priced at S$460 found 1 day ago
Delta
Tue, 7 Oct - Fri, 17 Oct
SJU
San Juan
ORD
Chicago
S$503 Return, found 1 day ago
S$503
Return
found 1 day ago
Select Delta flight, departing Tue, 7 Oct from San Juan to Chicago, returning Fri, 17 Oct, priced at S$503 found 1 day ago
Delta
Tue, 4 Nov - Fri, 14 Nov
SJU
San Juan
ORD
Chicago
S$513 Return, found 1 day ago
S$513
Return
found 1 day ago
Select Delta flight, departing Tue, 4 Nov from San Juan to Chicago, returning Fri, 14 Nov, priced at S$513 found 1 day ago
United
Tue, 7 Oct - Fri, 17 Oct
SJU
San Juan
ORD
Chicago
S$519 Return, found 1 day ago
S$519
Return
found 1 day ago
Select United flight, departing Tue, 7 Oct from San Juan to Chicago, returning Fri, 17 Oct, priced at S$519 found 1 day ago
American Airlines
Tue, 7 Oct - Fri, 17 Oct
SJU
San Juan
ORD
Chicago
S$523 Return, found 1 day ago
S$523
Return
found 1 day ago
Select American Airlines flight, departing Tue, 7 Oct from San Juan to Chicago, returning Fri, 17 Oct, priced at S$523 found 1 day ago
Delta
Tue, 4 Nov - Fri, 14 Nov
SJU
San Juan
ORD
Chicago
S$529 Return, found 1 day ago
S$529
Return
found 1 day ago
Select Delta flight, departing Tue, 4 Nov from San Juan to Chicago, returning Fri, 14 Nov, priced at S$529 found 1 day ago
Delta
Tue, 7 Oct - Fri, 17 Oct
SJU
San Juan
ORD
Chicago
S$537 Return, found 1 day ago
S$537
Return
found 1 day ago
Select Delta flight, departing Tue, 7 Oct from San Juan to Chicago, returning Fri, 17 Oct, priced at S$537 found 1 day ago
Delta
Tue, 7 Oct - Sat, 18 Oct
SJU
San Juan
ORD
Chicago
S$548 Return, found 1 day ago
S$548
Return
found 1 day ago
Select Delta flight, departing Tue, 7 Oct from San Juan to Chicago, returning Sat, 18 Oct, priced at S$548 found 1 day ago
United
Tue, 7 Oct - Fri, 17 Oct
SJU
San Juan
ORD
Chicago
S$551 Return, found 1 day ago
S$551
Return
found 1 day ago
Select United flight, departing Tue, 7 Oct from San Juan to Chicago, returning Fri, 17 Oct, priced at S$551 found 1 day ago
Delta
Tue, 4 Nov - Fri, 14 Nov
SJU
San Juan
ORD
Chicago
S$554 Return, found 1 day ago
S$554
Return
found 1 day ago
Select Delta flight, departing Tue, 4 Nov from San Juan to Chicago, returning Fri, 14 Nov, priced at S$554 found 1 day ago

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

January is typically the cheapest month to fly

From S$152 - S$664 per traveller.

Graph displaying average flight prices per month

San Juan to Chicago route information
Origin airport
Luis Munoz Marin Intl.
Destination airport
O'Hare Intl.
Airlines serving
American Airlines, Delta, United
Return price
S$460
Distance
3317 km
Average flight time
4 hours 11 mins

Perfect flights from San Juan to Chicago

Your Journey from San Juan to Chicago

Start your unforgettable journey with Expedia. Our broad selection of flights from San Juan to Chicago 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. Our selection of flights from Luis Munoz Marin Intl. to O'Hare 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 San Juan to Chicago Flights

Experience the joy of finding cheap flights from Luis Munoz Marin Intl. to O'Hare 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$460*.
 

Pre-Flight Essentials

Ensure a smooth journey from San Juan to Chicago 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 Chicago

Picture yourself stepping off the plane in Chicago and immersing yourself in the unique atmosphere of Chicago. 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 San Juan to Chicago 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 San Juan to Chicago.
 

Beyond the Flight – Exploring Chicago

With Expedia, your adventure extends beyond the flight. Explore Chicago 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 San Juan to Chicago 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 San Juan to Chicago 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 Luis Munoz Marin Intl. Airport (SJU) to O'Hare Intl. Airport (ORD)?
Based on fares quoted within the last 7 days on Expedia for flights departing within the next year, round-trip flights from SJU to ORD start from S$460. Make your booking today to score the best price for your next big adventure. Prices and availability are subject to change. Additional terms apply.
Do I need to pay a cancellation fee if I cancel my flight from Luis Munoz Marin Intl. Airport (SJU) to ORD?
Each airline has different terms and conditions. If you decide to cancel your escape, head to our Customer Service Portal.
How do I find cheap flights from Luis Munoz Marin Intl. Airport (SJU) to O'Hare Intl. Airport (ORD) 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 SJU to O'Hare Intl. Airport (ORD) flights, you'll see a "no change fees" filter for you to select.
How far is the flight from Isla Verde Intl. Airport to O'Hare Airport?
It's around 3,300 kilometres from Carolina to Chicago, so you'll be in your seat for a while. Keep yourself occupied by packing things like crossword puzzles or the latest bestseller.
Which airlines fly direct from SJU to O'Hare Intl. Airport (ORD)?
With 30 monthly flights from Luis Munoz Marin Intl. Airport (SJU) to O'Hare Intl. Airport (ORD), United Airlines (UA) is a popular choice. Offering 17 flights per month on this route, American Airlines (AA) is another fantastic option.
Are Isla Verde Intl. Airport to ORD flight tickets cheaper when they're purchased at the last minute?
Booking your trip from SJU to O'Hare Intl. Airport (ORD) last minute could save you some serious cash. However, it could end up costing you a whole lot more! If you'd prefer not to take the risk, book well ahead of your departure date. In fact, Expedia has some of the best bargains as far ahead as 12 months in advance. If your preferred carrier hasn't released tickets yet, check back often as deals are updated on Expedia all the time.

Explore a world of travel with Expedia

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