Find Cheap Flights from Chicago (CHI) to San Juan (SJU) from

Cheap flights from Chicago to San Juan 

Our advanced search tools and comprehensive filters help you find a flight that fits your budget. To search for cheap flights, just enter your travel dates and sort your results by price. With all available tickets listed lowest price first, it’s easy to select the one that’s easiest on your wallet.  

To find the cheapest flights from Chicago to San Juan, you can also travel outside peak season. The more flexible you can be on travel dates, the easier it is to find those cheap flight tickets. We know, for example, that the cheapest time to travel between Chicago to San Juan is . In the current list of deals available, prices start at and can rise to for return flights.  

Find the best flight from Chicago to San Juan  

Every day between Chicago and San Juan, 6 flights from 6 airlines jet back and forth. And with ebookers, you can book tickets for any one of those flights. If you book a direct flight with American Airlines, Alaska Airlines, Air Canada, Air New Zealand, United Airlines, Spirit Airlines, you’ll arrive safely in your destination in around 4hours. If you can think of a quicker way to cover the 3337 km between null and null, let us know! 

Flights from Chicago to San Juan — a great choice on great deals 

We only need a little information to give you a lot of choice. Just tell us when you’re planning your family holiday, long weekend, luxury getaway or quick business trip, and we’ll do the rest. And to keep your choice-making easy, we’ve given you plenty of ways to narrow down your search. Choose one-way, roundtrip or multi city flights, select your preferred airline, your time of arrival and departure and cabin class using the filters.  

Once you’ve told us what you want, we’ll show you what’s on offer. All you need to do is take your pick and start packing.  

Book your flights with ebookers 

We want the experience of booking your flight from Chicago to San Juan to be as simple as possible. That’s why we designed our search and filter options to make your life easy. Whether you are travelling on business or for pleasure, ebookers has you covered. 

When you’re ready to book, our service is always fast and transparent. We know plans change, so we have a range of flexible booking options. Choose between refundable bookings and flights with no charges should you need to rearrange and travel stress-free.