Deal found on September 16, 2026
Chicago to San Juan
$208$44053% off
Round trip
San Juan usually costs around $386 out of Chicago, but it's down to $208 right now, a 46 percent drop. Dates are flexible through the fall, and beyond the beaches, Old San Juan's cobblestone streets and salsa clubs make this more than just a layover stop.
Travel dates
February into March
e.g. Feb 23 – Mar 4 · 9 nights
Date options
26 at this price
Lowest we've seen
$128
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