￥20,670 Cheap Flights from Chicago (ORD) to San Juan (SJU)

View ￥20,670 flight on Wed, Dec 31, 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 ￥20,670 for one-way flights and ￥35,140 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Tue, Jan 13 - Fri, Jan 30
ORD
Chicago
SJU
San Juan
￥35,140 Roundtrip, found 4 days ago
￥35,140
Roundtrip
found 4 days ago
Select Delta flight, departing Tue, Jan 13 from Chicago to San Juan, returning Fri, Jan 30, priced at ￥35,140 found 4 days ago
Delta
Wed, Dec 31 - Wed, Jan 14
ORD
Chicago
SJU
San Juan
￥38,240 Roundtrip, found 4 days ago
￥38,240
Roundtrip
found 4 days ago
Select Delta flight, departing Wed, Dec 31 from Chicago to San Juan, returning Wed, Jan 14, priced at ￥38,240 found 4 days ago
Delta
Tue, Jan 13 - Mon, Jan 26
ORD
Chicago
SJU
San Juan
￥42,940 Roundtrip, found 4 days ago
￥42,940
Roundtrip
found 4 days ago
Select Delta flight, departing Tue, Jan 13 from Chicago to San Juan, returning Mon, Jan 26, priced at ￥42,940 found 4 days ago
American Airlines
Sun, Jan 11 - Thu, Jan 29
ORD
Chicago
SJU
San Juan
￥43,730 Roundtrip, found 4 days ago
￥43,730
Roundtrip
found 4 days ago
Select American Airlines flight, departing Sun, Jan 11 from Chicago to San Juan, returning Thu, Jan 29, priced at ￥43,730 found 4 days ago
American Airlines
Mon, Jan 12 - Sat, Jan 24
ORD
Chicago
SJU
San Juan
￥44,440 Roundtrip, found 4 days ago
￥44,440
Roundtrip
found 4 days ago
Select American Airlines flight, departing Mon, Jan 12 from Chicago to San Juan, returning Sat, Jan 24, priced at ￥44,440 found 4 days ago
Delta
Wed, Dec 31 - Fri, Jan 16
ORD
Chicago
SJU
San Juan
￥46,040 Roundtrip, found 4 days ago
￥46,040
Roundtrip
found 4 days ago
Select Delta flight, departing Wed, Dec 31 from Chicago to San Juan, returning Fri, Jan 16, priced at ￥46,040 found 4 days ago
American Airlines
Wed, Dec 31 - Tue, Jan 13
ORD
Chicago
SJU
San Juan
￥47,120 Roundtrip, found 4 days ago
￥47,120
Roundtrip
found 4 days ago
Select American Airlines flight, departing Wed, Dec 31 from Chicago to San Juan, returning Tue, Jan 13, priced at ￥47,120 found 4 days ago
American Airlines
Thu, Jan 1 - Tue, Jan 13
ORD
Chicago
SJU
San Juan
￥47,830 Roundtrip, found 4 days ago
￥47,830
Roundtrip
found 4 days ago
Select American Airlines flight, departing Thu, Jan 1 from Chicago to San Juan, returning Tue, Jan 13, priced at ￥47,830 found 4 days ago
Delta
Tue, Jan 13 - Sat, Jan 24
ORD
Chicago
SJU
San Juan
￥48,340 Roundtrip, found 4 days ago
￥48,340
Roundtrip
found 4 days ago
Select Delta flight, departing Tue, Jan 13 from Chicago to San Juan, returning Sat, Jan 24, priced at ￥48,340 found 4 days ago
United
Sun, Jan 11 - Wed, Jan 28
ORD
Chicago
SJU
San Juan
￥50,820 Roundtrip, found 4 days ago
￥50,820
Roundtrip
found 4 days ago
Select United flight, departing Sun, Jan 11 from Chicago to San Juan, returning Wed, Jan 28, priced at ￥50,820 found 4 days ago

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

March is typically the cheapest month to fly

From ￥20,560 - ￥51,557 per traveler.

Alternative airports near San Juan

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to Luis Munoz Marin Intl. SJU. Cheapest option available. Average driving time to city center is 16 minutes. Flights from ￥74,920
SJU
Luis Munoz Marin Intl.
Cheapest
Average driving time to city center16 min
Flights from ￥74,920
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
￥35,140
Distance
3317 km
Average flight time
6 hours 41 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 ￥35,140. 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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