$84 Cheap Flights from Chicago (ORD) to San Juan (SJU)

View $84 flight on Sat, May 10, 2025Opens in a new window

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

Find available prices by choosing your travel dates.

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

Prices were available within the past 7 days and start at $84 for one-way flights and $190 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Spirit Airlines
Sat, May 10 - Sun, May 11
ORD
Chicago
SJU
San Juan
$190 Roundtrip, found 2 hours ago
$190
Roundtrip
found 2 hours ago
Select Spirit Airlines flight, departing Sat, May 10 from Chicago to San Juan, returning Sun, May 11, priced at $190 found 2 hours ago
Spirit Airlines
Sat, May 10 - Fri, May 23
ORD
Chicago
SJU
San Juan
$193 Roundtrip, found 10 hours ago
$193
Roundtrip
found 10 hours ago
Select Spirit Airlines flight, departing Sat, May 10 from Chicago to San Juan, returning Fri, May 23, priced at $193 found 10 hours ago
Spirit Airlines
Fri, May 9 - Sat, May 10
ORD
Chicago
SJU
San Juan
$199 Roundtrip, found 1 hour ago
$199
Roundtrip
found 1 hour ago
Select Spirit Airlines flight, departing Fri, May 9 from Chicago to San Juan, returning Sat, May 10, priced at $199 found 1 hour ago
Spirit Airlines
Sat, May 10 - Fri, May 16
ORD
Chicago
SJU
San Juan
$205 Roundtrip, found 1 hour ago
$205
Roundtrip
found 1 hour ago
Select Spirit Airlines flight, departing Sat, May 10 from Chicago to San Juan, returning Fri, May 16, priced at $205 found 1 hour ago
Spirit Airlines
Fri, May 9 - Sun, May 11
ORD
Chicago
SJU
San Juan
$212 Roundtrip, found 4 hours ago
$212
Roundtrip
found 4 hours ago
Select Spirit Airlines flight, departing Fri, May 9 from Chicago to San Juan, returning Sun, May 11, priced at $212 found 4 hours ago
Spirit Airlines
Mon, May 19 - Fri, May 23
ORD
Chicago
SJU
San Juan
$215 Roundtrip, found 2 hours ago
$215
Roundtrip
found 2 hours ago
Select Spirit Airlines flight, departing Mon, May 19 from Chicago to San Juan, returning Fri, May 23, priced at $215 found 2 hours ago
Frontier Airlines
Thu, May 8 - Sat, May 10
ORD
Chicago
SJU
San Juan
$248 Roundtrip, found 5 hours ago
$248
Roundtrip
found 5 hours ago
Select Frontier Airlines flight, departing Thu, May 8 from Chicago to San Juan, returning Sat, May 10, priced at $248 found 5 hours ago
United
Tue, Sep 23 - Tue, Sep 30
ORD
Chicago
SJU
San Juan
$298 Roundtrip, just found
$298
Roundtrip
just found
Select United flight, departing Tue, Sep 23 from Chicago to San Juan, returning Tue, Sep 30, priced at $298 just found
Delta
Tue, Sep 16 - Wed, Sep 17
ORD
Chicago
SJU
San Juan
$302 Roundtrip, found 1 day ago
$302
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Sep 16 from Chicago to San Juan, returning Wed, Sep 17, priced at $302 found 1 day ago
American Airlines
Sun, Aug 24 - Thu, Sep 18
ORD
Chicago
SJU
San Juan
$303 Roundtrip, found 1 hour ago
$303
Roundtrip
found 1 hour ago
Select American Airlines flight, departing Sun, Aug 24 from Chicago to San Juan, returning Thu, Sep 18, priced at $303 found 1 hour ago
Flights from Chicago (ORD) to San Juan (SJU)
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
$189
Distance
2073 mi

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 May. 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 $84 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.

Frequently asked questions

How much does a flight from O'Hare Intl. Airport (ORD) to Luis Munoz Marin Intl. Airport (SJU) cost?
You can score cheap return tickets from O’Hare Intl. Airport (ORD) to Luis Munoz Marin Intl. Airport (SJU) starting from $212. Grab your seat and be on your way. This information is based on the cheapest price found on Expedia for this return journey departing within the next three months. This airfare is for a Spirit Airlines flight leaving ORD on May 12 2025 and touching down at SJU. The price was last updated on April 24 2025 and has not changed since.
What is the cheapest month to fly from ORD to SJU?
The cheapest flights from ORD to SJU are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
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 ORD to SJU?
At the moment, the cheapest airline offering one-way flights from ORD to SJU is Spirit Airlines. You can jet off on this route from $106. This fare is based on the lowest price found on Expedia departing within the next three months. The flight takes off from ORD on May 19 2025. Prices were last updated on April 24 2025 and have not changed since.
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.

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*Available to One Key members.