$114 Cheap flight deals from Chicago (CHI) to San Juan (SJU)

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This Weekend's Flight Deals from Chicago to San Juan

This weekend's flight prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Airfares from $114 One Way, $236 Round Trip from Chicago to San Juan

Prices starting at $236 for return flights and $114 for one-way flights to San Juan were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

San Juan economy flight packages

Price found within the past 48 hours. Click for updated prices.
El Colonial - Adults Only
Fairmont El San Juan Villa Experience
Romeo Gay Hotel
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San Juan packages with premium economy flights

Price found within the past 48 hours. Click for updated prices.
 Ciqala Suites Hotel
El Colonial - Adults Only
Fairmont El San Juan Villa Experience
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San Juan first class flight packages

Price found within the past 48 hours. Click for updated prices.
El Colonial - Adults Only
The Condado Plaza Hotel
Fairmont El San Juan Villa Experience
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More About Flying To San Juan from Chicago

Route Information for Flights from Chicago to San Juan

Origin Airport IATA Code
CHI
Destination Airport IATA Code
SJU
Distance
2073 mi
Direct Flight Airlines
American Airlines, Air Canada, Alaska Airlines, Air New Zealand, United Airlines
Earliest Flight Arrival
6:06PM UTC
Latest Flight Arrival
3:54AM UTC

Chicago to San Juan

Getting a spectacularly low fare on Chicago to San Juan flights is always possible when you use Orbitz as your personal travel planner. Orbitz is your essential travel resource for low cost flights from Chicago to San Juan, discount hotel accommodations, cheap car rentals, and more.

Research and Book Chicago to San Juan Flights on the Go

Our free cutting-edge mobile apps for iPad, Android, and iPhone make it easy to find the best fares when researching and booking flights from Chicago to San Juan. You can also use the apps to check your flight status, find baggage claims details, and get exclusive mobile discount rates on car rentals and hotels.

Earn Miles and Points for Your Frequent Flyer Program

Build up points or miles for your frequent flyer plan with qualifying Chicago to San Juan flights. Simply add your frequent flyer number when booking your domestic or international flights or enter the numbers in your Orbitz account profile to automatically add them to your bookings.

Flight Alerts Take the Hassle out of Travel

You can get email, SMS text, or voicemail updates regarding any major changes to your flights from Chicago to San Juan. These free alerts can also be sent to as many as six additional contacts, ensuring that your friends, colleagues, or family are aware of changes to your arrival time.

Stay in Your Budget and Still Get Great Accommodations

Orbitz shoppers can access affordable vacation packages and have the option of booking their departure and arrival flights through different airlines, making travel less costly and more convenient. The best prices on flights from Chicago to San Juanare always found on Orbitz.

Frequently asked questions

Am I able to catch a flight from Chicago to San Juan now?
Go right to our Covid-19 Travel Advisor for the most up-to-date information on quarantine and travel restrictions when catching a flight from Chicago to San Juan.
Are there non-stop flights from Chicago to San Juan?
You betcha. In fact, there are 3 airlines that fly direct from ORD to Isla Verde Intl. Airport. Book a ticket with one of these popular carriers:
  • American Airlines
  • Frontier Airlines
  • United Airlines
  • American Airlines
  • Frontier Airlines
  • United Airlines
What is the shortest flight from Chicago to San Juan?
From Chicago, the unique sights and sounds of San Juan are at least 4 hours and 46 minutes away. Lock in your favorite seat, or maybe even one with extra legroom, and fly to your destination in comfort.
What airlines fly from Chicago to San Juan most frequently?
American Airlines (AA) is one of the airlines with the most flights from ORD to Isla Verde Intl. Airport. It offers 60 flights each month on this route. Taking off on a vacation is one of life’s greatest pleasures, and this carrier will get you to your destination quickly and safely. Also check out the great airfares from Frontier Airlines (F9). Offering 30 flights each month between Chicago and San Juan, they’ll ensure your journey is just as delightful as the destination.
If I am not able to travel due to COVID-19, can I cancel my flight to San Juan?
We get that traveling right now has its challenges, so it’s good to know that many reservations booked through us are able to be cancelled or changed. If your travel plans to San Juan have been affected by COVID-19, a lot of airlines are making things easier by offering credits to use at a later date. Just sign in to your account and you’ll quickly see what options are available. Our Customer Service Portal is the place to go for more information.
Are there flights to San Juan with flexible change policies?
In most cases you’ll have the option to reschedule your flight to San Juan without a change fee. All you have to do then is pay the difference between the old flight and the new one. Look for the “no change fees” filter and book with confidence.
What is the cheapest day of the week to fly?
Consider flying out early in the week to save on your airfare. Orbitz data from 2020 shows that Monday is the cheapest day to depart, followed by Tuesday. Saturday showed the highest average ticket prices likely because many travelers prefer to start their vacation on a weekend.
What is the cheapest month to fly?
We won’t keep you guessing, according to Orbitz data the cheapest month to fly is August. Perfect for those who need a weekend getaway, or just a break from it all before the weather changes. Be aware that the most expensive time to fly is the height of summer, with ticket prices peaking in the month of June.
How can I save money on flights?
To really save big on your next vacation, think outside the box. Select two different airlines or fare types for your return trip and you’ll generally get a much better deal. Those who tried this on Orbitz in 2020 saved up to 45% on their airfares. Get mixing and matching today!

Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.