$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.
San Agustin Apartments
Dorado Beach 5 Bedroom Villa
Coral by the Sea Hotel
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San Juan first class flight packages

Price found within the past 48 hours. Click for updated prices.
Hyatt Vacation Club at Hacienda del Mar, Dorado
DADA JAJA by DW
DREAMCATCHER by DW - ADULTS ONLY
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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
Direct Flight Airlines
Earliest Flight Arrival
Latest Flight Arrival

Chicago to San Juan

For the best available deals on flights from Chicago to San Juan, look no further than Orbitz. Offering the perfect packages with cutting-edge mobile tools, Orbitz is your ideal destination.

One Stop Travel Shop

Not only is Orbitz the best source for great deals on flights from Chicago to San Juan, we offer the complete package. From guaranteed low prices on hotels, car rentals and activities, simply decide what you want and Orbitz will put together the complete vacation package.

Searching Anywhere

Booking Chicago to San Juan flights is simple, wherever you are. Book on your computer and the Orbitz Display Matrix gives all your deals and discounts on flights from Chicago to San Juan, showing your great savings. Or if you are on the move, use m.orbitz.com on your mobile browser to find exclusive Chicago to San Juan flights for mobile users.

Worry-free Travel Planning

Orbitz is the best place for Chicago to San Juan flights at guaranteed low prices, we also take the stress out of your flight details. With our free alerts service you can quickly find out your gate number or flight delays via email or text – perfect if you are in a rush.

Miles Better

If you frequently travel on flights from Chicago to San Juan, it’s easy to rack up your air miles. Just add your frequent flyer number when booking your flights and we will do the rest. Orbitz will even store your number in your profile to automatically add on your miles each time you book.

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.