$287 — San Juan, P.R., from Chicago Nonstop (R/T, w/Tax)

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:


  • 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:


Chicago-San Juan: Fly.com Search Results

Chicago-San Juan: jetBlue Results Page

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Featured Image: Luquillo Beach (Shutterstock.com)

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