Chicago to San Diego, USA from $219 September 18, 2026April 21, 2026 by aifly Chicago → San Diego · F9 · from $219
Chicago to San Juan, Puerto Rico from $227 July 2, 2026April 11, 2026 by aifly Chicago → San Juan, Puerto Rico · United · from $227
Chicago to Algiers, Algeria from $576 September 23, 2026April 10, 2026 by aifly Chicago → Algiers, Algeria · Turkish Airlines · from $576
Chicago to Bogota, Colombia from $321 September 23, 2026April 6, 2026 by aifly Chicago → Bogota, Colombia · United · from $321
Chicago to Cartagena, Colombia from $333 July 2, 2026March 26, 2026 by aifly chicago → cartagena · from USD333
Chicago to Medellin, Colombia from $392 July 2, 2026March 25, 2026 by aifly chicago → medellin · from USD392
