Cheap Flights from Chicago (ORD) to San Juan (SIG)

Popular airlines from Chicago O'Hare Intl. Airport (ORD) to San Juan (SIG-Fernando Luis Ribas Dominicci)

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 $266
SJU
Luis Munoz Marin Intl.
Cheapest
Average driving time to city center16 min
Flights from $266

Frequently asked questions

How much does a flight from O'Hare Intl. Airport (ORD) to Fernando Luis Ribas Dominicci Airport (SIG) cost?
Secure a cheap one-way flight or cheap return flight from O'Hare Intl. Airport (ORD) to Fernando Luis Ribas Dominicci Airport (SIG) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight deals on this route.
What is the cheapest month to fly from O'Hare Intl. Airport (ORD) to Fernando Luis Ribas Dominicci Airport (SIG)?
The cheapest month to fly from ORD to SIG is , when there's less demand. Off-peak season is generally when you'll find cheap fares for travel between these airports.
What is the cheapest airline that flies from O'Hare Intl. Airport (ORD) to Fernando Luis Ribas Dominicci Airport (SIG)?
To find the cheapest airline that'll fly you from ORD to SIG, use Expedia's filter tool. Tailor your search based on what matters most to you, such as preferred carriers and number of stops. You can then sort your results by "Price (lowest to highest)" to see the most affordable options first.
How many flights per day from O'Hare Intl. Airport (ORD) to Fernando Luis Ribas Dominicci Airport (SIG)?
Nonstop flights from O'Hare Intl. Airport (ORD) to Fernando Luis Ribas Dominicci Airport (SIG) aren't available daily, so you'll have to take a flight with a layover. Explore your options with Expedia's filters. Enter your dates and pick either "1 Stop" or "2+ Stops."
What day of the week has the most flights from ORD to SIG?
You'll generally find Tuesday the quietest day for flights, while Fridays are often the busiest.* However this can vary from season to season and during peak travel times or public holidays.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from O'Hare Intl. Airport (ORD) to Fernando Luis Ribas Dominicci Airport (SIG)?
Book a flight from O'Hare Intl. Airport (ORD) to Fernando Luis Ribas Dominicci Airport (SIG) that takes off before 3 PM to reduce the likelihood of delays. Departures after this time are on average 22% more likely to be canceled.**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.
Is it cheaper to buy a plane ticket from O'Hare Intl. Airport (ORD) to Fernando Luis Ribas Dominicci Airport (SIG) last-minute?
Holding off until just before your trip to book a flight from ORD to SIG generally means paying more. While it's possible to find some last-minute discounts, they aren't always guaranteed. Allow some flexibility in your schedule for a better chance of getting a bargain.
Can I cancel or change the date of my flight from O'Hare Intl. Airport (ORD) to Fernando Luis Ribas Dominicci Airport (SIG)?
If you booked your ORD to SIG flight in the last 24 hours, you may be able to cancel or modify it without any fees. Depending on the airline and the type of fare you have, additional charges may apply for changes beyond this timeframe. Airline policies and contact information can be found in your itinerary or confirmation email. Or, go to our Customer Service portal if you'd like more information.

Travel information

Origin airport
O'Hare Intl.
Destination airport
Fernando Luis Ribas Dominicci
Distance
2069 mi

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 . 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 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.