What’s the cost of a flight from Chicago O'Hare to Isla Grande?

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

Choose a date to explore the best fares now.

If possible, avoid holiday periods: ticket prices tend to rise quickly and availability drops, especially on busy routes. Morning and evening flights are often in high demand too — book early to get a good fare.

Planning flights between Chicago and San Juan? Don’t forget the airport options

Especially when flying to medium or large cities, it's worth checking all possible airport combinations before booking.

• Airports in Chicago: 3 airports are listed in Chicago - Midway, O'Hare, Rockford.
• Airports in San Juan: Only San Juan - Isla Grande is currently available.

Check for differences in transport costs to and from each airport — they affect your total spend. Choosing the right airport can make a real difference in price and timing.

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 the best airlines and travel agencies.

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.