Cheap Flights from Chicago to San Juan
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Fares from Chicago to San Juan by month.
Across 4 months of observations from Chicago to San Juan, the lowest round-trip economy fare we recorded was $94, in August. The typical economy fare was $363. August was the cheapest month we saw and November the dearest.
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Economy price history: Chicago to San Juan
The lowest fares we saw each month.
| Month | Low | Typical | Sightings |
|---|---|---|---|
| Nov 2026 | $194 | $370 | 135 |
| Oct 2026 | $172 | $409 | 450 |
| Sep 2026 | $178 | $384 | 230 |
| Aug 2026 | $94 | $290 | 366 |
Frequently asked questions
How many flight deals from Chicago to San Juan are on Sparkflights right now?
There are 0 deals from Chicago to San Juan on the board right now.
What is the lowest price ever seen from Chicago to San Juan?
The lowest economy fare we've recorded from Chicago to San Juan is $94, based on 1181 price observations over 4 months.
How much does a flight from Chicago to San Juan cost?
The typical round-trip economy fare we observed from Chicago to San Juan is $363, against a recorded low of $94. These are observations, not quotes.
When is the cheapest month to fly Chicago to San Juan?
For economy fares from Chicago to San Juan, August was the cheapest month we observed and November the dearest, over 4 months of data.