What’s the cost of a flight from Chicago Midway 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.

Which departure and arrival airports are available?

Between Chicago and San Juan, flight options may depend on the combination of airports available.

• Airports in Chicago: Chicago is connected by 3 airports - Midway, O'Hare, Rockford.
• Airports in San Juan: Another alternative is Isla Grande.

Sometimes flying into a nearby city can be more cost-effective. When a city has multiple airports, it’s worth comparing different flight combinations.

Explore flights from Chicago Midway to San Juan your way

On Jetcost, you can filter by round-trip or one-way, time of day, airline, number of stops, and even by specific travel agency.

Other popular destinations

Also interested in Puerto Rico? Check out: Aguadilla, Culebra Airport, Ponce, San Juan, Vieques Airport.

If you’re flexible with dates, try checking the days before and after to see if prices vary. Some routes are offered by multiple agencies — comparing fares can really pay off.