Deals from Chicago – AiFly

✈️ No Commissions — Honest Flight Deals Every Day

✈ All Deals 🌍 Europe 🌎 Americas 🌏 Asia Pacific 🌍 Africa

Chicago to Medellín, Colombia from $348

September 14, 2026 by aifly

Medellín landmark in Medellín

Chicago → Medellín · Arajet · from $348

Chicago to Copenhagen, Denmark from $428

September 14, 2026September 14, 2026 by aifly

Copenhagen landmark in Copenhagen

Chicago → Copenhagen · Icelandair · from $428

Chicago to Tirana, Albania from $665

September 11, 2026September 11, 2026 by aifly

Tirana landmark in Tirana

Chicago → Tirana · Air Serbia · from $665

Chicago to Barcelona, Spain from $573

September 10, 2026September 10, 2026 by aifly

Barcelona landmark in Barcelona

Chicago → Barcelona · Lufthansa · from $573

Chicago to Warsaw, Poland from $654

September 9, 2026 by aifly

Warsaw landmark in Warsaw

Chicago → Warsaw · Turkish Airlines · from $654

Chicago to Cartagena, Colombia from $385

September 8, 2026 by aifly

Cartagena landmark in Cartagena

Chicago → Cartagena · Copa Airlines · from $385

Chicago to Reykjavik, Iceland from $355

September 6, 2026September 6, 2026 by aifly

Jökulsárlón glacier lagoon, Iceland — turquoise icebergs below the Vatnajökull ice cap on a clear day

Chicago → Reykjavik · Icelandair · from $355

Chicago to Mexico City, Mexico from $237

September 2, 2026 by aifly

Mexico City landmark in Mexico City

Chicago → Mexico City · Volaris · from $237

Chicago to Calgary, Canada from $271

August 30, 2026August 30, 2026 by aifly

Calgary landmark in Calgary

Chicago → Calgary · WestJet / Air Canada · from $271

Chicago to Monterrey, Mexico from $253

August 23, 2026August 22, 2026 by aifly

Monterrey landmark in Monterrey

Chicago → Monterrey · Viva Aerobus · from $253

Chicago to Copenhagen, Denmark from $531

August 23, 2026August 22, 2026 by aifly

Copenhagen landmark in Copenhagen

Chicago → Copenhagen · SAS · from $531

Chicago to Lima, Peru from $330

August 21, 2026August 9, 2026 by aifly

Lima landmark in Lima

Chicago → Lima · Arajet / Volaris · from $330

Chicago to Cairo, Egypt from $664

August 6, 2026August 6, 2026 by aifly

Cairo landmark in Cairo

Chicago → Cairo · Turkish Airlines · from $664

Chicago to San Juan, Puerto Rico from $216

September 3, 2026August 5, 2026 by aifly

San Juan landmark in San Juan

Chicago → San Juan · Frontier · from $216

Chicago to Entebbe, Uganda from $896

August 24, 2026July 27, 2026 by aifly

A lioness resting in a tree in western Uganda

Chicago → Entebbe · Qatar Airways · from $896

✈ Find your deal ✎