Book cheap flights from Chicago to San Juan from £42
Chicago
San Juan
Mon, 06 Jan
ORD - SJU
Mon, 13 Jan
SJU - ORD
£152
£141
Prime price per passenger
Chicago
San Juan
Tue, 28 Jan
ORD - SJU
£46
£42
Prime price per passenger
Chicago
San Juan
Mon, 20 Jan
ORD - SJU
Sat, 25 Jan
SJU - ORD
£111
£102
Prime price per passenger
Chicago
San Juan
Wed, 01 Jan
ORD - SJU
Thu, 09 Jan
SJU - ORD
£332
£326
Prime price per passenger
Chicago
San Juan
Tue, 07 Jan
MDW - SJU
Mon, 13 Jan
SJU - MDW
£197
£194
Prime price per passenger
Chicago
San Juan
Mon, 13 Jan
ORD - SJU
Sat, 18 Jan
SJU - ORD
£129
£119
Prime price per passenger
Booking a flight from Chicago to San Juan
Booking your flight through eDreams is simple. Just enter Chicago and San Juan as your departure and destination cities, choose the dates of your trip, and search through the available options. Our search engine will find the best deals from thousands of routes and flight combinations.
We also offer a ‘Smart Choice’ option, by which we highlight the most competitive flights at the top of the search results. You can also apply filters to view only flights to San Juan from your preferred airlines.
Changes to the price of your flights during your booking
Flight fares are set up using a complex pricing algorithm based on demand and seat availability. As a result, the cost of your flight may vary during your booking process. To secure the best price for your flight to San Juan, make sure you book as soon as you find a flight ticket that suits your pocket.
eDreams Prime members discounts
As an eDreams Prime member, you can access exclusive deals and save hundreds on flights, hotels, and car hires, along with many other benefits. Join the world’s largest travel membership community and discover all the advantages of eDreams Prime.
Last-minute bookings with eDreams
eDreams also offers last-minute flights at competitive prices. While these may be more expensive, we provide a range of options to suit your needs. Keep in mind, though, that last-minute prices can be higher, particularly during peak travel season. Being flexible with your travel dates can increase your chances of finding better deals.
Checking in before your flight
Online check-in usually opens 24 to 48 hours before the departure time. Once your booking with eDreams is completed, we’ll email you one week before your day of departure with instructions on how to check in for your flight.
Best season to travel from Chicago to San Juan
Puerto Rico offers endless possibilities, from its rich gastronomy to its diverse culture and stunning nature. The best time to travel depends on your preferences and availability. Always consider the climate, peak tourist season, and the type of experience you’re seeking.
Expect larger crowds during peak season, but you'll also enjoy a lively atmosphere and more cultural and touristic offerings. Travelling off-season usually means fewer crowds, lower prices on flights and accommodations, and a more authentic glimpse into local life. While some outdoor activities may be limited due to the weather conditions, popular attractions will likely be less crowded, allowing for a more immersive experience.
Flight Time
5 h and 2 m
Flights from Chicago and San Juan last around 5 h and 2 m, although this flight time may also depend on other factors.
Cheapest flight
£42
The cheapest price available for flights from Chicago to San Juan that have been booked by our customers in the last 72 hours
Airport of Departure
O'hare International Airport
You will depart from O'hare International Airport when flying from Chicago to San Juan
Airport of Arrival
Luis Munoz Marin International
Outbound flights from Chicago to San Juan arrive at Luis Munoz Marin International