￥26,220 Cheap Flights from Chicago (ORD) to San Juan (SJU)

View ￥26,220 flight on Sat, Nov 8, 2025Opens in a new window

Popular airlines from Chicago O'Hare Intl. Airport (ORD) to Luis Munoz Marin Intl. Airport (SJU)

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

Prices were available within the past 7 days and start at ￥26,220 for one-way flights and ￥47,980 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

American Airlines
Mon, Feb 9 - Tue, Feb 10
ORD
Chicago
SJU
San Juan
￥47,980 Roundtrip, found 3 days ago
￥47,980
Roundtrip
found 3 days ago
Select American Airlines flight, departing Mon, Feb 9 from Chicago to San Juan, returning Tue, Feb 10, priced at ￥47,980 found 3 days ago
American Airlines
Sat, Oct 25 - Thu, Oct 30
ORD
Chicago
SJU
San Juan
￥51,760 Roundtrip, found 1 day ago
￥51,760
Roundtrip
found 1 day ago
Select American Airlines flight, departing Sat, Oct 25 from Chicago to San Juan, returning Thu, Oct 30, priced at ￥51,760 found 1 day ago
Delta
Sat, Oct 25 - Thu, Oct 30
ORD
Chicago
SJU
San Juan
￥52,440 Roundtrip, found 1 day ago
￥52,440
Roundtrip
found 1 day ago
Select Delta flight, departing Sat, Oct 25 from Chicago to San Juan, returning Thu, Oct 30, priced at ￥52,440 found 1 day ago
American Airlines
Wed, Dec 3 - Sat, Dec 6
ORD
Chicago
SJU
San Juan
￥52,800 Roundtrip, found 6 days ago
￥52,800
Roundtrip
found 6 days ago
Select American Airlines flight, departing Wed, Dec 3 from Chicago to San Juan, returning Sat, Dec 6, priced at ￥52,800 found 6 days ago
American Airlines
Sat, Dec 13 - Fri, Dec 19
ORD
Chicago
SJU
San Juan
￥55,050 Roundtrip, found 5 days ago
￥55,050
Roundtrip
found 5 days ago
Select American Airlines flight, departing Sat, Dec 13 from Chicago to San Juan, returning Fri, Dec 19, priced at ￥55,050 found 5 days ago
American Airlines
Sat, Oct 25 - Thu, Oct 30
ORD
Chicago
SJU
San Juan
￥55,060 Roundtrip, found 1 day ago
￥55,060
Roundtrip
found 1 day ago
Select American Airlines flight, departing Sat, Oct 25 from Chicago to San Juan, returning Thu, Oct 30, priced at ￥55,060 found 1 day ago
American Airlines
Sat, Dec 13 - Fri, Dec 19
ORD
Chicago
SJU
San Juan
￥55,720 Roundtrip, found 5 days ago
￥55,720
Roundtrip
found 5 days ago
Select American Airlines flight, departing Sat, Dec 13 from Chicago to San Juan, returning Fri, Dec 19, priced at ￥55,720 found 5 days ago
American Airlines
Sat, Nov 8 - Tue, Nov 11
ORD
Chicago
SJU
San Juan
￥55,740 Roundtrip, found 14 hours ago
￥55,740
Roundtrip
found 14 hours ago
Select American Airlines flight, departing Sat, Nov 8 from Chicago to San Juan, returning Tue, Nov 11, priced at ￥55,740 found 14 hours ago
American Airlines
Sat, Feb 7 - Tue, Feb 10
ORD
Chicago
SJU
San Juan
￥56,080 Roundtrip, found 3 days ago
￥56,080
Roundtrip
found 3 days ago
Select American Airlines flight, departing Sat, Feb 7 from Chicago to San Juan, returning Tue, Feb 10, priced at ￥56,080 found 3 days ago
United
Sat, Oct 25 - Thu, Oct 30
ORD
Chicago
SJU
San Juan
￥63,460 Roundtrip, found 1 day ago
￥63,460
Roundtrip
found 1 day ago
Select United flight, departing Sat, Oct 25 from Chicago to San Juan, returning Thu, Oct 30, priced at ￥63,460 found 1 day ago

Find the cheapest month to fly from Chicago (ORD) to San Juan (SJU)

January is typically the cheapest month to fly

From ￥17,386 - ￥54,953 per traveler.
Flights from Chicago (ORD) to San Juan (SJU)
Origin airport
O'Hare Intl.
Destination airport
Luis Munoz Marin Intl.
Airlines serving
American Airlines, Delta, United
Roundtrip price
￥47,980
Distance
3317 km
Average flight time
5 hours 45 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 ￥47,980. 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.

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