How to find the cheapest flight from
Chicago (CHI) to Puerto Rico
How far in advance should I book a flight from Chicago to Puerto Rico?
Travelers have found it’s best to book a flight 41 days in advance to save up to 11% compared to booking the same week of travel. As your travel date approaches, the cost of this flight route may potentially increase. While opting to book 41 days out may not be an option for all, there are still additional ways to secure a deal in the near future. You might find a flight from Chicago to Puerto Rico 1-2 weeks in advance for as low as $380, or $415 for flights within the next 24 hours.
What is the cheapest month to fly from Chicago to Puerto Rico?
Our data shows that September tends to be the cheapest month to fly to Puerto Rico from Chicago. Users have commonly found prices around $380 for the month, but tickets can be as low as $194. Due to multiple factors, prepare for potentially higher prices in December.
One-way flights to Puerto Rico from Chicago
The cheapest one-way flights from Chicago to Puerto Rico
2:00 am - 11:56 am
2:00 am - 5:12 pm
5:25 pm - 4:36 pm
Related info for your journey
Useful info, stats and facts about Chicago to Puerto Rico flights.
Arrival points for flights from Chicago to Puerto Rico
Destination information for Puerto Rico
Things to know before you go. Useful info for your trip from Chicago to Puerto Rico
Chicago Midway (MDW)
Ceiba J. Aponte de la Torre (NRR)