Recent Airfares from Chicago to Puerto Rico

Chicago to San Juan

from

2024-08-23 - 2024-08-26
Direct · 3-day round trip
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Chicago to Aguadilla

from

2025-02-13 - 2025-02-17
1 stop · 4-day round trip
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Chicago to Culebra

from

2025-02-13 - 2025-02-17
2+ stops · 4-day round trip
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Chicago to Vieques

from

2025-02-13 - 2025-02-17
2+ stops · 4-day round trip
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Weather Averages for Puerto Rico

Explore Popular Cities in Puerto Rico

San Juan Puerto Rico Culebra Puerto Rico Ceiba Puerto Rico Vieques Puerto Rico Ponce Puerto Rico Aguadilla Puerto Rico Mayaguez Puerto Rico Maleza Puerto Rico El Combate Puerto Rico San Antonio Puerto Rico

Chicago to Puerto Rico flight information

  • The most popular flight routes from Chicago to Puerto Rico are Chicago to San Juan, Chicago to Aguadilla
  • The cheapest flight from Chicago to Puerto Rico is from Chicago to San Juan, with airfares starting at EUR 255.17
  • The fastest flight from Chicago to Puerto Rico is from Chicago to San Juan, with an average flight time of 4h 40m
  • The most popular airlines flying from Chicago to Puerto Rico are United Airlines
  • The most popular city destinations in Puerto Rico are San Juan, Culebra, Ceiba

Popular Airlines flying from Chicago to Puerto Rico

United Airlines ‏()

Popular routes from Chicago to Puerto Rico

Popular destinations from Chicago