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Chicago to Puerto Rico flight

Flying From Chicago to Puerto Rico: What You Need to Know

Cheapest one-way flight price$72
Cheapest round-trip ticket price$153
Off-season for travelOctober
Peak season for travelJuly
Popular airlineSpirit Airlines
Cheapest monthSeptember

Compare multiple airlines at once to find the best flight deals from Chicago to Puerto Rico.

Airlines Flying From Chicago to Puerto Rico
Spirit Airlines logo Spirit Airlines
United Airlines logo United Airlines
Jetblue Airways logo Jetblue Airways
American Airlines logo American Airlines
Delta Air Lines logo Delta Air Lines
Frontier Airlines logo Frontier Airlines

Search Flights From Chicago to Puerto Rico

Easily compare flights from Chicago to Puerto Rico and find the cheapest tickets available!

Looking for cheap flights from Chicago to Puerto Rico? Check out prices for the next 90 days, starting at just $72 for a one-way ticket and $153 for a round trip.

Displayed flight fares from Chicago to San Juan are based on average prices across airlines for the next 3 months, according to the latest Trip.com database.

FAQs: Flights From Chicago to Puerto Rico

  • What is the cheapest Chicago to Puerto Rico flight route?

    The cheapest round-trip flight from Chicago to Puerto Rico is on the route from Chicago to San Juan, with prices starting at $150 for a round trip between 2026-05-16 and 2026-05-22.
  • According to our flights calendar over the next 90 days, it seems the cheapest date is on 2026-05-05 for one-way flights.
  • Based on our flight data, the average flight time from Chicago to Puerto Rico is approximately 4 hours 49 minutes based on our most popular routes from Chicago to San Juan. The time may also vary depending on your destination.
  • The cheapest airline flying to Puerto Rico from Chicago is Spirit Airlines serving route from Chicago to San Juan.
  • There are direct flights from Chicago to Puerto Rico. San Juan, Aguadilla, and Ponce are all popular destinations in Puerto Rico.