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Book $255 Cheap American Airlines flights from Chicago (CHI) to San Juan (SJU)

Flight deals from Chicago to San Juan

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Prices shown below were available within the past 3 days for the period specified and should not be considered the final price offered. Please note that availability and prices are subject to change.

American Airlines flight deals from Chicago to San Juan

Chicago San Juan
BEST
DEAL
Mon, 17 Mar ORD - SJU
$261 $255
Prime price per passenger

Best flight offers from other airlines

Chicago San Juan
BEST
DEAL
Tue, 24 Dec MDW - SJU
Wed, 25 Dec SJU - MDW
$375 $364
Prime price per passenger
Chicago San Juan
BEST
DEAL
Mon, 23 Dec ORD - SJU
Wed, 25 Dec SJU - ORD
$394 $383
Prime price per passenger
Chicago San Juan
BEST
DEAL
Mon, 23 Dec ORD - SJU
Wed, 25 Dec SJU - ORD
$395 $384
Prime price per passenger
Chicago San Juan
BEST
DEAL
Fri, 20 Dec ORD - SJU
Wed, 25 Dec SJU - ORD
$421 $409
Prime price per passenger
Chicago San Juan
BEST
DEAL
Fri, 20 Dec ORD - SJU
Wed, 25 Dec SJU - ORD
$424 $414
Prime price per passenger
Chicago San Juan
BEST
DEAL
Sun, 22 Dec ORD - SJU
Wed, 25 Dec SJU - ORD
$451 $439
Prime price per passenger

Get your flight with American Airlines to San Juan from Chicago starting at $255

The Best Chicago to San Juan Flight Deals with American Airlines

With eDreams, finding the best American Airlines deals for your trip from Chicago to San Juan couldn’t be easier. Imagine this: exclusive discounts, intuitive booking tools, and plenty of helpful perks—all at your fingertips! Say goodbye to the hassle of planning and hello to the excitement of your upcoming adventure in San Juan.

Whether you’re looking for unbeatable prices, a custom-fit itinerary, or some extra perks, eDreams is your all-in-one travel partner for every part of the Chicago (CHI) to San Juan (SJU) journey. Stick around to find out why booking with eDreams is the best way to kick off your trip.

Flying from Chicago to San Juan with American Airlines

Flying from Chicago (CHI) to San Juan (SJU) with American Airlines (AA) is all about comfort and convenience. From check-in to touchdown, American Airlines ensures a smooth experience, so you can just sit back and relax. You’ll find fast check-ins, extra legroom, and attentive service designed for a stress-free trip.

Once onboard, the friendly crew will make sure you have everything you need. Many routes offer in-flight Wi-Fi, so you can stay connected, binge-watch shows, or catch up on work if you need to. Feeling hungry? American Airlines has a great selection of snacks and meals to keep you satisfied mid-flight. And if you want a bit more luxury, you can treat yourself to upgrades and priority boarding, adding a personal touch to your journey. With great service and a focus on a smooth, enjoyable flight, American Airlines makes your trip from Chicago to San Juan easy and fun.

Book Your Flight with eDreams and Enjoy the Perks

Booking affordable flights from Chicago (CHI) to San Juan (SJU) with eDreams isn’t just about getting a great deal—it’s about making travel planning effortless. With eDreams, you get awesome perks that make your journey easier and more enjoyable:

Your Journey from Chicago to San Juan with American Airlines

The journey from Chicago (CHI) to San Juan (SJU) is all about getting you to your destination comfortably and quickly, so your adventure can start as soon as you land. This direct route offers plenty of options, whether you prefer a quick non-stop flight or more flexibility with layovers. Whatever your style, there’s a schedule that fits.

Departing from Chicago and Arriving at San Juan: What to Expect

When departing from Chicago, enjoy easy airport access, clear signage, and quick check-ins for a stress-free start. You’ll breeze through security, leaving plenty of time to relax before takeoff.

When you land in San Juan, you’ll be greeted by a modern terminal with plenty of transportation options like taxis, buses, and shuttles to get you on your way. Whether heading to your hotel or diving into sightseeing, everything you need is right there.

Best Time to Book Your Chicago — San Juan Trip with American Airlines

For the best American Airlines flight deals from Chicago to San Juan, timing is everything! Booking in advance often means lower fares, especially during off-peak seasons when San Juan is quieter and flights are more budget-friendly. Check the climate to plan for the ideal weather to suit your trip—whether for mild outdoor adventures or cultural explorations. With a bit of planning, you’re set for an unforgettable getaway!

American Airlines Chicago-San Juan flights FAQ's

Which airports does American Airlines fly between Chicago and San Juan?
For flights between Chicago and San Juan, American Airlines operates the following airport routes: For flights between Chicago and San Juan, American Airlines operates from the following airport routes: O hare International Airport (ORD) to Luis Munoz Marin International (SJU)
What do American Airlines flights from Chicago to San Juan cost?
One of American Airlines cheapest prices for a Chicago to San Juan flight we have right now is $255. On average though, flights with American Airlines cost $260.97 for the route Chicago to San Juan, but it mostly depends on the season and how far in advance you book your tickets.
Cheapest Ticket Price $255 The most affordable rate found in the last 72 hours for flights operated by American Airlines leaving from Chicago and going to San Juan, according to our customers' bookings.
Flight Time 5 h and 2 m The American Airlines flight duration between Chicago and San Juan is around 5 h and 2 m, however it could be affected by other circumstances.
Departure Airport O'hare International Airport Your departure will be from O'hare International Airport, when flying with American Airlines from Chicago to San Juan.
Arrival Airport Luis Munoz Marin International When flying with American Airlines from Chicago to San Juan, your arrival airport will be O'hare International Airport.

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