￥39,133 Cheap flights from Chicago (ORD) to San Juan (SJU)

Featured airlines

Plan, book, fly with confidence

Be in the know
Get alerts if flight prices drop or rise*
Book smarter
Save up to 40% on select hotels after you book a flight*
Earn twice
Earn your airline miles on top of our rewards
Sign in

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

Prices were available within the past 7 days and start at ￥39,133 for one-way flights and ￥75,079 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

All deals

One way

Roundtrip

Fri, Mar 14 - Sat, Mar 22

ORD

Chicago

SJU

San Juan

￥75,079

Roundtrip

found 3 days ago

Wed, Jul 24 - Mon, Jul 29

ORD

Chicago

SJU

San Juan

￥75,856

Roundtrip

found 4 days ago

Fri, Mar 14 - Sat, Mar 22

ORD

Chicago

SJU

San Juan

￥76,088

Roundtrip

found 3 days ago

Sat, Jun 8 - Sun, Jun 9

ORD

Chicago

SJU

San Juan

￥76,200

Roundtrip

found 2 days ago

Fri, Mar 14 - Sat, Mar 22

ORD

Chicago

SJU

San Juan

￥76,788

Roundtrip

found 3 days ago

Fri, Mar 14 - Sat, Mar 22

ORD

Chicago

SJU

San Juan

￥80,751

Roundtrip

found 3 days ago

Fri, Mar 14 - Sat, Mar 22

ORD

Chicago

SJU

San Juan

￥81,218

Roundtrip

found 3 days ago

Fri, Mar 14 - Sat, Mar 22

ORD

Chicago

SJU

San Juan

￥82,227

Roundtrip

found 3 days ago

Wed, Jul 24 - Mon, Jul 29

ORD

Chicago

SJU

San Juan

￥82,694

Roundtrip

found 4 days ago

Fri, Mar 14 - Sat, Mar 22

ORD

Chicago

SJU

San Juan

￥82,927

Roundtrip

found 3 days ago

Flights from Chicago (ORD) to San Juan (SJU)
Origin airport	O'Hare Intl.
Destination airport	Luis Munoz Marin Intl.
Roundtrip price	￥75,079
Distance	3317 km
Average flight time	5 hours 47 mins

Chicago to San Juan Flights

Sometimes you just need to get out of town or maybe you’re looking for a change of scenery. Regardless of the reason, a flight from Chicago to will do just the trick! Go on, plan to see all the famous landmarks and eat your weight in the local cuisine. Your trip is beckoning, so answer the call by packing your suitcase and filling your travel itinerary with exploring San Juan.

Whether you’re flying for business or jet-setting on your personal time, you’ve come to the right place. Here at Expedia.com, we’ll pair you up with ORD to SJU flights that won’t make your bank account wince. Ready to temporarily leave behind Chicago for new horizons? Browse through our cheap airfare, and filter by flight times and dates until you find just what you had in mind. From flights without layovers to ones that arrive early in the morning, you’ll come across plane tickets that suit your travel preferences. You can even bundle your flight to SJU with hotels and car rentals to score even bigger savings.

All set to hit the clouds? Book your travel arrangements with us today and have left-over money to put toward your travel outings and adventures.

Frequently asked questions

How much is a flight from ORD to SJU?

Start packing your suitcase, because round-trip flights between O’Hare Airport and SJU start from ￥75,079. That’s based on fares advertised within the last 7 days on Expedia for flights departing within the next year. Prices can change quickly, so book now to lock in the best deal. Prices and availability are subject to change. Additional terms apply.

Do I need to pay a cancellation fee if I cancel my flight from O'Hare Airport to SJU?

The majority of flights can be conveniently canceled online, but whether you incur a fee all comes down to your airline. If you do have to cancel your break, follow the easy instructions in the Customer Service Portal.

How do I find cheap flights from O'Hare Intl. Airport (ORD) to SJU 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 O’Hare Airport to SJU flights, you’ll see a “no change fees” filter for you to select.

How many hours is the flight from ORD to Luis Munoz Marin Intl. Airport (SJU)?

There are plenty of ways to make the 6 hours and 41 minutes between O’Hare Intl. Airport (ORD) and Isla Verde Intl. Airport go by quicker. If you want to be productive, sort through your camera roll or clear out all those backed-up emails. A nice snooze also helps pass the time!

How far is the flight from O'Hare Intl. Airport (ORD) to SJU?

Expect to be cruising at altitude for a while, as the flight distance from Chicago to Carolina is 3,300 kilometers. Put together a playlist of your favorite podcasts before leaving home to stay entertained during the journey.

Which airlines fly direct from O'Hare Intl. Airport (ORD) to Luis Munoz Marin Intl. Airport (SJU)?

With 30 monthly flights from ORD to SJU, United Airlines (UA) is a top choice. Like some more options? Check out the seats available with Spirit Airlines (NK). This carrier offers 26 flights every month between these airports.

Are ORD to SJU flight tickets cheaper when they're purchased at the last minute?

Flight tickets from ORD to SJU are available up to a year before departure on Expedia. And although you may nab a fantastic last-minute deal, it’s never something you can count on. Also, booking your flights in advance means you’ll have more choices — and you can avoid being wedged in the dreaded middle seat! We frequently update our fares to bring you the best bargains, so check back often for all the latest specials.