January 21, 2026 Chicago to Dubai, UAE for only $561 roundtrip Cheap flights from Chicago to Dubai, UAE for only $561 roundtrip with Turkish Airlines.
January 19, 2026 Chicago to German cities from only $184 one-way Cheap flights from Chicago to German cities from only $184 one-way with American Airlines and British Airways.
January 18, 2026 Chicago to French cities from only $186 one-way Cheap flights from Chicago to French cities from only $186 one-way with British Airways.
January 16, 2026 Chicago to Dublin, Ireland for only $359 roundtrip Cheap flights from Chicago to Dublin, Ireland for only $359 roundtrip.
January 13, 2026 Non-stop from Chicago to Reykjavik, Iceland for only $378 roundtrip Non-stop flights from Chicago to Reykjavik, Iceland for only $378 roundtrip.
January 12, 2026 Non-stop from Chicago to Cancun, Mexico for only $281 roundtrip Non-stop flights from Chicago to Cancun, Mexico for only $281 roundtrip with United Airlines.
January 6, 2026 Non-stop from Chicago to Seattle (& vice versa) for only $133 roundtrip Non-stop flights from Chicago to Seattle for only $133 roundtrip with Alaska Airlines. Also works in reverse.
January 4, 2026 Chicago to Oslo, Norway for only $377 roundtrip Cheap flights from Chicago to Oslo, Norway for only $377 roundtrip with Scandinavian Airlines.
December 31, 2025 Chicago to Kahului, Hawaii (& vice versa) for only $382 roundtrip Cheap flights from Chicago to Kahului, Hawaii for only $382 roundtrip with Alaska Airlines. Also works in reverse.