Open interactive map →Cheap flights from Chicago to San Juan
Planning a trip from Chicago to San Juan? Current fares start at €118 - a solid entry point for a flight to Puerto Rico. Several airlines compete on this route, which helps keep fares relatively stable. Direct and one-stop options are both available - use the booking site to filter by preference. Use the price calendar to identify your cheapest month, then click through to compare live seat availability.
Prices to San Juan are typically lowest in the shoulder months shown in the calendar above. Searching for mid-week flights and avoiding school holiday windows can meaningfully cut costs on this route. If you're open on destination, use the interactive map from Chicago to compare San Juan against nearby alternatives - you may find a cheaper fare to a similar destination.
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Cheapest month to fly
- October 2026€1182 stopsCheapest
Based on tracked fares, October is the cheapest month to fly this route at around €118.
Prices last updated: September 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 fare currently available from Chicago to San Juan is €118. Prices on this route vary by season, day of week, and how far in advance you book. The month-by-month price calendar on this page shows exactly when fares are highest and lowest, so you can pick the most cost-effective window before searching for specific dates. Fares are refreshed regularly as our flight partners publish new availability.
Are there direct flights from Chicago to San Juan?
SkyHopp tracks both direct and connecting flights from Chicago to San Juan. Connecting flights are often priced lower but add travel time due to the layover. Whether a non-stop option exists on specific dates depends on airline schedules - use the "Direct only" filter on the interactive map to see non-stop options, or check the booking site for a full breakdown by stop count.
When is the cheapest time to fly from Chicago to San Juan?
Prices on this route typically dip during shoulder-season months, away from school holidays and public holiday windows. Mid-week departures - particularly Tuesday to Thursday - tend to be cheaper than flights on Fridays and Sundays from Chicago. The month-by-month price calendar above is the fastest way to identify the cheapest window - look for the months with the lowest fares before committing to travel dates. Booking 3-6 weeks in advance generally offers the best balance of price and seat availability on this route.