Find out what a flight from Chicago to San Juan might cost

Prices vary based on date, airline, and availability. Compare several options if you're flying between Chicago and San Juan.

Select your dates to check current offers.

Try shifting your departure forward or backward by a day to find better options. If you’re looking for a good deal, consider flying outside peak hours as well.

Are there alternative airports near Chicago and San Juan?

The two cities are about 3314 km apart. Looking beyond the main airport might reveal better options.

• Airports in Chicago: There are 3 airports in Chicago - Midway, O'Hare, Rockford.
• Airports in San Juan: Isla Grande is another nearby option to San Juan - Luis Muñoz Marín.

Many smaller airports are connected by direct buses or shuttles, often at low cost. If San Juan has more than one airport, you can pick the most convenient for your destination.

Smart ways to search flights from Chicago to San Juan

Use Jetcost to view tailored results based on what you care about — time, duration, number of stops, or even your preferred booking agency. Results include the best airlines and travel agencies.

Other popular destinations

Flying to Puerto Rico? Other travelers also searched: Aguadilla, Culebra Airport, Mayaguez, Ponce, San Juan.

Prefer non-stop flights? Just activate the filter to skip unnecessary layovers. If your dates are flexible, you can also explore different departure and return combinations to find the best fit.