Flights from Chicago to San Juan

Prices displayed are approximate based on recent fare research and fluctuate based on specific travel dates, seasonal demand, booking timing, airport choice (ORD vs MDW), and airline. Lowest fares have limited availability and require advance booking.

United Airlines fares include one personal item and carry-on bag free (basic economy). Checked bags $30-40 first bag. United MileagePlus members earn miles. Frontier and Spirit are ultra-low-cost carriers - base fares exclude all bags (carry-on $35-65, checked $30-70), seat selection, and food/beverages.

Most economy fares non-refundable with change fees $75-200. Premium cabin upgrades available on United (Economy Plus, Premium Plus, Polaris Business). Book through airline websites or travel sites (Google Flights, Expedia, Kayak). Peak winter holiday periods have significantly higher fares. Subject to airline availability and fare conditions.

Find nonstop flights from Chicago to San Juan, Puerto Rico with one-way fares starting at $143. Both Chicago O'Hare International Airport (ORD) and Midway International Airport (MDW) offer direct service to Luis Muñoz Marín International Airport (SJU) on Frontier Airlines, United Airlines, and Spirit Airlines, with flight times of approximately 4 hours and 30 minutes.

Chicago is an important Midwest gateway to Puerto Rico, with service from both major airports providing excellent options for the entire Chicagoland area and connecting passengers from across the Midwest. United offers their mainline service with connectivity across their global network, while Frontier and Spirit provide budget-friendly alternatives.

The nonstop flight makes Puerto Rico easily accessible from America's heartland, perfect for escaping harsh Midwest winters for Caribbean warmth. With multiple carriers competing on this route, prices can be very competitive especially when booking in advance.

Winter is peak season as Chicagoans flee snow and cold for sunny beaches. Book 2-3 months ahead for the best deals, particularly for December-March travel. Tuesday and Wednesday departures typically offer the lowest fares. Perfect for winter breaks, spring getaways, or summer beach vacations.