Route Price Intelligence
Cheap Flights From Chicago to San Juan
Live pricing benchmarks, monthly patterns, and historical lows for this route.
ORD to San Juan is down to $138, well off the usual $307 for this route and just a few dollars above the cheapest fare we've ever recorded here. Puerto Rico needs no passport and has some of the best beaches in the Caribbean, so a fare this close to record-low territory is worth grabbing while it's live.
✓ 3 date combinations found at this price
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Best Time to Fly from Chicago to San Juan
The cheapest time to fly from Chicago to San Juan is typically September, when fares average around $326. The most expensive month tends to be April at around $702. For the best deals, consider flying in September, October, November.
Typical Price by Travel Month
Median round-trip fare for each month, with the typical price range, from our ongoing tracking of this route