Planning a flight from Chicago O'Hare to Isla Grande?

Flight prices from Chicago to San Juan change depending on demand and time of booking.

Choose a date to explore the best fares now.

Many users find better fares by booking several weeks in advance. In fact, for many routes, booking early is one of the best ways to save.

Flights between Chicago and San Juan: which airports can you choose?

The distance between Chicago and San Juan is about 3330 km. Checking alternative airports can help lower the total cost of your trip.

• Airports in Chicago: Chicago is served by 3 airports - Midway, O'Hare, Rockford.
• Airports in San Juan: Currently, the only available airport in San Juan is San Juan - Isla Grande.

Choosing airports with fast connections to the city center can cut down total travel time. You can compare all flights from Chicago airports to find the best option.

Customize your flight from Chicago O'Hare to Isla Grande

Jetcost allows you to filter by travel dates, duration, layovers, carriers, and booking providers. You’ll find direct and connecting flights, one-way or round-trip, from Ryanair, Easyjet, British Airways, Expedia, eDreams, and more.

Other popular destinations

Thinking about Puerto Rico? You might also consider: Aguadilla, Culebra Airport, Mayaguez, Ponce, San Juan.

You can sort results by price, duration, or departure time to find the best option for you. When available, results always include both low-cost and traditional airlines.