Chicago to Cartagena, Colombia from $385 September 8, 2026 by aifly Chicago → Cartagena · Copa Airlines · from $385
Chicago to Calgary, Canada from $271 August 30, 2026August 30, 2026 by aifly Chicago → Calgary · WestJet / Air Canada · from $271
Stockholm to Chicago, USA from €312 August 25, 2026August 24, 2026 by aifly Stockholm, Sweden → Chicago · Scandinavian Airlines · from €312
Chicago to Cairo, Egypt from $664 September 23, 2026August 6, 2026 by aifly Chicago → Cairo · Turkish Airlines · from $664
Chicago to San Juan, Puerto Rico from $216 September 3, 2026August 5, 2026 by aifly Chicago → San Juan · Frontier · from $216
Gothenburg to Chicago, USA from €410 September 18, 2026July 22, 2026 by aifly Gothenburg, Sweden → Chicago · Finnair · from €410
Chicago to Cartagena, Colombia from $295 September 20, 2026July 7, 2026 by aifly Chicago → Cartagena · JetBlue · from $295
Vilnius to Chicago, USA from €410 July 3, 2026July 3, 2026 by aifly Vilnius → Chicago · Scandinavian Airlines · from €410
Vilnius to Chicago, USA from €421 September 16, 2026June 12, 2026 by aifly Vilnius → Chicago · Finnair · from €421
Chicago to Cartagena, Colombia from $285 September 12, 2026May 8, 2026 by aifly Chicago → Cartagena · from $285
Chicago to Cartagena, Colombia from $333 September 21, 2026April 28, 2026 by aifly Chicago → Cartagena · Copa Airlines · from $333
Chicago to Calgary, Canada from $265 September 18, 2026April 28, 2026 by aifly Chicago → Calgary · Delta Air Lines · from $265
Chicago to Delhi, India from $562 September 18, 2026April 23, 2026 by aifly Chicago → Delhi · AC · from $562
Chicago to San Juan, Puerto Rico from $256 September 7, 2026April 22, 2026 by aifly Chicago → San Juan · AA · from $256
Chicago to Portland, USA from $195 September 18, 2026April 21, 2026 by aifly Chicago → Portland · AA · from $195
