Chicago to San Juan, Puerto Rico from $227

⚠️ United Basic Economy: checked bag is a paid add-on.

🌍 About San Juan, Puerto Rico

I have what I need. Here's the card: San Juan packs nearly all its draw into Old San Juan, a small grid of 16th-century streets paved with adoquines — blue-gray cobblestones cast from iron-furnace slag that Spanish ships carried over as ballast. At its tip sits El Morro, a six-level fort whose cannons guarded the harbor for 400 years; the grassy approach is where locals fly kites on Sunday afternoons. Eat mofongo: green plantains fried, mashed with garlic and pork crackling, packed into a bowl and filled with shrimp or stewed conch — order it relleno, not as a side. December through April brings dry, warm days but the highest prices and crowds. The cheap fares land in September and October, the heart of hurricane season, so book those with travel insurance and a flexible eye on the forecast.