Deal found on October 4, 2026
Chicago to San Juan
$178$40556% off
Round trip
This San Juan fare usually runs about $570+ round trip, and it just dropped to $178, a 69% cut on the MDW-SJU route. Dates are opening up across the fall and winter calendar for Old San Juan's cobblestone streets and beach time, no passport needed. Frontier keeps it to one connection, which is how the price stays this low.
Travel dates
October into November
e.g. Oct 24 – Nov 2 · 9 nights
Date options
3 at this price
Lowest we've seen
$154
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