Open interactive map →Cheap flights from Chicago to San Juan
Planning a trip from Chicago to San Juan? Tracked fares start at €129 to Puerto Rico. Tracked fares on this route include at least one stop. Use the price calendar to compare months SkyHopp has data for, then click through to check seats and dates.
A price calendar on this page lists tracked months as they fill in. Tracked fares on this route include at least one stop. If you are open on destination, use the interactive map from Chicago to compare San Juan against nearby alternatives.
One-way fares
From €129
Cheapest tracked fare
Return fares
From €180
Tracked return fares (out 23 Nov 2026, back 2 Dec 2026)
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Get an email when Chicago to San Juan fares are at or below your target price. The email includes the fare.
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Cheapest month to fly
- November 2026€1291 stopCheapest
SkyHopp has tracked fares for this route in November at around €129. That is the only month with data so far, so it is too early to name a cheapest month.
Cheapest fare last seen 26 October 2026.
Alternative routes
Other ways to reach San Juan
Frequently asked questions
How much does a flight from Chicago to San Juan cost?
The cheapest tracked fare from Chicago to San Juan is €129. The month-by-month price calendar on this page lists the months SkyHopp has fares for. A tracked return fare on this pair is currently from €180. Fares are refreshed as our flight partners publish new availability.
Are there direct flights from Chicago to San Juan?
SkyHopp has not observed a non-stop fare from Chicago to San Juan in the current dataset. Tracked fares on this pair include at least one stop. Schedules change - check the booking site for a full breakdown by stop count on your dates.
When is the cheapest time to fly from Chicago to San Juan?
SkyHopp does not yet have enough months of fares on this route to name a cheapest month. The calendar above lists the months that already have data. Set a price alert on this page to watch the fare.