Plan a getaway from the Midwest’s winter! Nonstop flights to San Juan, Puerto Rico, from Chicago are now available for just $287 roundtrip, including taxes.

Fly.com Fare Calendar:

Savings:

  • This fare represents a savings of up to $150 off typical rountrip pricing.

Travel Dates:

  • Departures available on select dates from November – April. The weeks surrounding and including Thanksgiving, Christmas and New Year’s are blacked out at this price.

Sample Screenshots:

 

CHI SJU Fly.com Search Results 300x81 $287 — San Juan, P.R., from Chicago  Nonstop (R/T, w/Tax)

Chicago-San Juan: Fly.com Search Results

CHI SJU jetBlue Results Page 300x220 $287 — San Juan, P.R., from Chicago  Nonstop (R/T, w/Tax)

Chicago-San Juan: jetBlue Results Page


Fly.com Updates

Here are a few ways to stay connected with us:

Featured Image: Luquillo Beach (Shutterstock.com)

Posted by

Kim has been hunting flight deals and writing travel articles for over 13 years. His articles have appeared in the Boston Herald, Chicago Daily Herald, and Frommer’s Budget Travel, among other publications. Amsterdam, Bangkok, Rome, and Sydney are some of his favorite destinations and he aspires to one day live in Italy. La dolce vita!

Find Cheap Flights

Add Fly.com to Your Circles

Sponsored Listings