$64 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 $64 One Way, $128 Round Trip from Chicago to San Juan

Prices starting at $128 for return flights and $64 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
Old San Juan Rentals
San Juan Water and Beach Club
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San Juan packages with premium economy flights

Price found within the past 48 hours. Click for updated prices.
San Agustin Apartments
El Colonial - Adults Only
San Juan Water and Beach Club
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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, Spirit Airlines
Earliest Flight Arrival
6:03PM UTC
Latest Flight Arrival
9:03PM UTC

Chicago to San Juan

If you have been putting off a well-deserved vacation due to a tight budget, now is the time to visit Orbitz.com. We offer you huge savings on Chicago to San Juan flights, great hotel rooms, and stellar vacation packages. Let Orbitz show you how to cheaply plan the perfect trip.

Guaranteed low prices on flights from Chicago to San Juan

Low fares, discounted rates, great deals, and special promotions—all of these can be found through Orbitz. Get cheap fares on Chicago to San Juan flights and amazing deals on luxury hotels. You can even accumulate loyalty or frequent flyer miles or points on qualifying flights from Chicago to San Juan so you can earn flight rewards on your favorite airlines.

Mobile planning for flights from Chicago to San Juan

Worried about unexpected flight delays or other travel disruptions on your Chicago to San Juan flights? You can opt to receive free alerts sent to you and six of your contacts via email, voicemail, or text. The Orbitz mobile app also lets you access up-to-date flight information from your iPhone, iPad, and mobile Android devices. Our mobile technology let you check baggage claim and gate details, view your itinerary for your flights from Chicago to San Juan, and book exclusive hotel deals—even on the same day.

Take advantage of low fares on Chicago to San Juan flights and vacation packages

Orbitz has the best prices available on flights from Chicago to San Juan. Take advantage of our low fare sales and discounts and begin to plan your next trip. We also give you great savings on hotels, car rentals, and vacation packages.

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.