What’s the cost of a flight from Chicago O'Hare to San Juan?

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.

Best airport options between Chicago and San Juan

If you're open to flying into or out of more than one airport, you’ll have more routes to compare.

• Airports in Chicago: Chicago is served by 3 airports - Midway, O'Hare, Rockford.
• Airports in San Juan: Isla Grande offers an alternative to San Juan - Luis Muñoz Marín.

Some airports offer extras like lounges, fast track, or self check-in — good to keep in mind. Comparing airports by services offered helps you balance cost and comfort.

Filter and compare flights from Chicago O'Hare to San Juan

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Other popular destinations

Want more ideas for your trip to Puerto Rico? Check these: Aguadilla, Culebra Airport, Ponce, San Juan, Vieques Airport.

Advanced filters help you skip long layovers or inconvenient times. The “airlines” filter is handy if you want to collect miles or prefer a certain onboard experience.