$69 Cheap Flights from Chicago (ORD) to San Juan (SJU)

View $69 flight on Mon, Feb 2, 2026Opens 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 $69 for one-way flights and $138 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frontier Airlines
Mon, Jan 26 - Thu, Feb 5
ORD
Chicago
SJU
San Juan
$138 Roundtrip, just found
$138
Roundtrip
just found
Select Frontier Airlines flight, departing Mon, Jan 26 from Chicago to San Juan, returning Thu, Feb 5, priced at $138 just found
Frontier Airlines
Mon, Jan 26 - Thu, Feb 5
ORD
Chicago
SJU
San Juan
$154 Roundtrip, just found
$154
Roundtrip
just found
Select Frontier Airlines flight, departing Mon, Jan 26 from Chicago to San Juan, returning Thu, Feb 5, priced at $154 just found
Frontier Airlines
Tue, Mar 3 - Wed, Mar 4
ORD
Chicago
SJU
San Juan
$158 Roundtrip, found 2 days ago
$158
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Tue, Mar 3 from Chicago to San Juan, returning Wed, Mar 4, priced at $158 found 2 days ago
Spirit Airlines
Sat, Dec 6 - Mon, Dec 15
ORD
Chicago
SJU
San Juan
$163 Roundtrip, found 2 hours ago
$163
Roundtrip
found 2 hours ago
Select Spirit Airlines flight, departing Sat, Dec 6 from Chicago to San Juan, returning Mon, Dec 15, priced at $163 found 2 hours ago
Frontier Airlines
Mon, Feb 2 - Fri, Feb 20
ORD
Chicago
SJU
San Juan
$170 Roundtrip, found 2 days ago
$170
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Mon, Feb 2 from Chicago to San Juan, returning Fri, Feb 20, priced at $170 found 2 days ago
Frontier Airlines
Thu, Jan 8 - Wed, Feb 4
ORD
Chicago
SJU
San Juan
$170 Roundtrip, found 1 day ago
$170
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Thu, Jan 8 from Chicago to San Juan, returning Wed, Feb 4, priced at $170 found 1 day ago
Frontier Airlines
Mon, Jan 26 - Thu, Feb 5
ORD
Chicago
SJU
San Juan
$176 Roundtrip, just found
$176
Roundtrip
just found
Select Frontier Airlines flight, departing Mon, Jan 26 from Chicago to San Juan, returning Thu, Feb 5, priced at $176 just found
Delta
Mon, Jan 26 - Thu, Feb 5
ORD
Chicago
SJU
San Juan
$183 Roundtrip, just found
$183
Roundtrip
just found
Select Delta flight, departing Mon, Jan 26 from Chicago to San Juan, returning Thu, Feb 5, priced at $183 just found
United
Mon, Feb 2 - Tue, Feb 3
ORD
Chicago
SJU
San Juan
$213 Roundtrip, found 8 hours ago
$213
Roundtrip
found 8 hours ago
Select United flight, departing Mon, Feb 2 from Chicago to San Juan, returning Tue, Feb 3, priced at $213 found 8 hours ago
American Airlines
Wed, Jan 28 - Wed, Feb 4
ORD
Chicago
SJU
San Juan
$218 Roundtrip, just found
$218
Roundtrip
just found
Select American Airlines flight, departing Wed, Jan 28 from Chicago to San Juan, returning Wed, Feb 4, priced at $218 just found

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

January is typically the cheapest month to fly

From $118 - $367 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 $220
SJU
Luis Munoz Marin Intl.
Cheapest
Average driving time to city center16 min
Flights from $220

Frequently asked questions

How much does a flight from O'Hare Intl. Airport (ORD) to Luis Munoz Marin Intl. Airport (SJU) cost?
Get a cheap one-way flight from $69 or cheap return flight from $138 from O'Hare Intl. Airport (ORD) to Luis Munoz Marin Intl. Airport (SJU) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to see our cheapest flight offers on this route.
What is the cheapest month to fly from O'Hare Intl. Airport (ORD) to Luis Munoz Marin Intl. Airport (SJU)?
Planning your trip for January can help you save, as it's the cheapest month for flights between ORD and SJU. You'll often find the lowest prices during the off-season.
Which airlines fly direct from O'Hare Intl. Airport (ORD) to Luis Munoz Marin Intl. Airport (SJU)?
Enjoy an uninterrupted journey to Luis Munoz Marin Intl. Airport (SJU). 3 carriers operate direct routes from O'Hare Intl. Airport (ORD), including:

  • United Airlines
  • Spirit Airlines
  • American Airlines

What is the cheapest airline that flies from O'Hare Intl. Airport (ORD) to Luis Munoz Marin Intl. Airport (SJU)?
While prices can vary depending on when you travel, American Airlines and Spirit Airlines are go-to choices for flights between O'Hare Intl. Airport (ORD) and Luis Munoz Marin Intl. Airport (SJU). You can also compare airlines on Expedia and use the "Sort by" filter to find the lowest fare for your ORD to SJU flight.
How many flights per day from O'Hare Intl. Airport (ORD) to Luis Munoz Marin Intl. Airport (SJU)?
With, on average, 3 direct flights departing from O'Hare Intl. Airport (ORD) to Luis Munoz Marin Intl. Airport (SJU) every day, you'll be off on your next adventure in no time.
What are the most popular departure times for flights from O'Hare Intl. Airport (ORD) to Luis Munoz Marin Intl. Airport (SJU)?
The 8 AM departures from ORD to SJU are the top choice for many travelers. These flights can come with a higher price due to their popularity. If you want to save on your fare, book during off-peak hours.
What day of the week has the most flights from ORD to SJU?
Friday has the most flights from O'Hare Intl. Airport (ORD) to Luis Munoz Marin Intl. Airport (SJU). Consider leaving on this day and you'll have a greater chance of finding a schedule that works for you.
What is the earliest flight from O'Hare Intl. Airport (ORD) to Luis Munoz Marin Intl. Airport (SJU)?
Take the earliest flight at around 7:20AM UTC-6, heading out of O'Hare Intl. Airport (ORD). You'll be in the air for around 4h 38m, touching down at Luis Munoz Marin Intl. Airport (SJU) at approximately 1:58PM UTC-4.
How long does it take to fly from O'Hare Intl. Airport (ORD) to Luis Munoz Marin Intl. Airport (SJU)?
It usually takes 4 hours and 36 minutes to fly the 2,100 mi from ORD to SJU.
What airline has the least delays from ORD to SJU?
With 100% of flights generally arriving as scheduled, Frontier Airlines has the best on-time performance for direct flights from O'Hare Intl. Airport (ORD) to Luis Munoz Marin Intl. Airport (SJU). To keep track of your flight status and get notifications about any changes, head to the Expedia App.
What is the best time to fly from O'Hare Intl. Airport (ORD) to Luis Munoz Marin Intl. Airport (SJU)?
To land at Luis Munoz Marin Intl. Airport (SJU) on time, select a flight that takes off from O'Hare Intl. Airport (ORD) before 3 PM. The chance of cancellations is 22% higher, on average, for departures after this time.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
What airports do you fly into for San Juan from O'Hare Intl. Airport (ORD)?
Explore your flight options from O'Hare Intl. Airport (ORD) to Luis Munoz Marin Intl. Airport (SJU). This is the only San Juan airport you can fly into if you're taking a direct flight.
Is it cheaper to buy a plane ticket from O'Hare Intl. Airport (ORD) to Luis Munoz Marin Intl. Airport (SJU) last-minute?
Booking your ticket from ORD to SJU just before your trip is generally more expensive. But if you're flexible with your itinerary, you could bag a cheap last-minute fare.
Can I cancel or change the date of my flight from O'Hare Intl. Airport (ORD) to Luis Munoz Marin Intl. Airport (SJU)?
Typically, it's possible to cancel or reschedule your ORD to SJU flight. However, if the booking was made more than 24 hours ago, additional charges may apply. Refer to your airline's policies in your itinerary to see what changes are possible and whether any costs are involved. You'll also find more details on our Customer Service portal.

Travel information

Origin airport
O'Hare Intl.
Destination airport
Luis Munoz Marin Intl.
Airlines serving
American Airlines, Delta, Frontier Airlines, JetBlue Airways, Southwest Airlines, Spirit Airlines, United
Roundtrip price
$138
Distance
2073 mi
Average flight time
6 hours 39 mins

Book with confidence

Chicago to San Juan Flights

The cheapest times to fly from Chicago to San Juan

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Chicago to San Juan are during the month of January. You can find some of the cheapest flights from Chicago to San Juan with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Chicago to San Juan

Sunday is one of the best days to book for cheap flights from Chicago to San Juan: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Chicago to San Juan

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Chicago to San Juan in 2025. You can also book with separate airlines for your outbound and return journeys, from $69 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Chicago to San Juan flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Chicago to San Juan airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Chicago to San Juan Flights

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*Available to One Key members.