Chicago to Cartagena, Colombia from $293

🌍 About cartagena

Cartagena's walled old town is the postcard, but the barrio that actually has a pulse is Getsemaní, a once-rough neighborhood now covered in murals where food carts pack Plaza de la Trinidad after dark. Eat an arepa de huevo — a corn patty split, stuffed with a whole egg, and deep-fried — sold from street stalls for pocket change. For a sit-down meal, order cazuela de mariscos, a coconut-milk seafood stew that's the city's signature dish, not the touristy ceviche cups on the wall. Go December to April, the dry season, with January to mid-March the driest and sunniest. Avoid October, the wettest month by far (around 230mm of rain). It's Caribbean-hot and humid year-round, so the good-weather months and the cheaper rainy fares are a genuine trade-off.