How much is a ticket from Chicago O'Hare to Isla Grande?

Depending on when you travel and how far in advance you book, fares between Chicago and San Juan can differ a lot.

Choose a date to explore the best fares now.

If you’re flexible with timing, consider overnight flights — they often cost less and are less crowded. Exploring multiple date and time combinations can help you find the cheapest solution.

Which airports near Chicago or San Juan offer flights?

In many cases, using a nearby airport can improve your chances of finding direct flights or better rates.

• Airports in Chicago: 3 airports are active - Midway, O'Hare, Rockford.
• Airports in San Juan: San Juan - Isla Grande is the only airport in use at the moment.

Secondary airports can offer faster travel thanks to shorter lines and quicker boarding times than major ones.

Plan your perfect flight from Chicago O'Hare to Isla Grande

Jetcost gives you full control over your flight search. Filter by date, time, duration, price, and airline. See round-trip and one-way options from low-cost and full-service carriers and more.

Other popular destinations

Planning a trip to Puerto Rico? Other frequent searches include: Aguadilla, Culebra Airport, Mayaguez, Ponce, San Juan.

Some airlines include baggage in the fare, others don’t — always check the details before booking. If you're looking for round-trip flights, you can easily see the most convenient combinations.