Chicago to Cartagena, Colombia from $285 May 10, 2026May 8, 2026 by aifly Chicago → Cartagena · from $285
Chicago to Cartagena, Colombia from $333 May 10, 2026April 28, 2026 by aifly Chicago → Cartagena · Copa Airlines · from $333
Chicago to Calgary, Canada from $265 May 6, 2026April 28, 2026 by aifly Chicago → Calgary · Delta Air Lines · from $265
Chicago to Delhi, India from $562 May 6, 2026April 23, 2026 by aifly Chicago → Delhi · AC · from $562
Chicago to San Juan, Puerto Rico from $256 May 4, 2026April 22, 2026 by aifly Chicago → San Juan · AA · from $256
Chicago to Portland, USA from $195 May 6, 2026April 21, 2026 by aifly Chicago → Portland · AA · from $195
Chicago to San Diego, USA from $219 May 6, 2026April 21, 2026 by aifly Chicago → San Diego · F9 · from $219
Chicago to San Juan, Puerto Rico from $227 April 30, 2026April 11, 2026 by aifly Chicago → San Juan, Puerto Rico · United · from $227
Chicago to Algiers, Algeria from $576 May 6, 2026April 10, 2026 by aifly Chicago → Algiers, Algeria · Turkish Airlines · from $576
Chicago to Bogota, Colombia from $321 May 4, 2026April 6, 2026 by aifly Chicago → Bogota, Colombia · United · from $321
Chicago to Cartagena, Colombia from $333 May 6, 2026March 26, 2026 by aifly chicago → cartagena · from USD333
Chicago to Medellin, Colombia from $392 May 6, 2026March 25, 2026 by aifly chicago → medellin · from USD392
