November 3, 2025 Chicago to Rio de Janeiro, Brazil for only $424 roundtrip Cheap flights from Chicago to Rio de Janeiro, Brazil for only $424 roundtrip with Copa Airlines.
November 1, 2025 Non-stop from Chicago to Reykjavik, Iceland for only $375 roundtrip Non-stop flights from Chicago to Reykjavik, Iceland for only $375 roundtrip.
October 31, 2025 Chicago to Sydney, Australia for only $770 roundtrip Cheap flights from Chicago to Sydney, Australia for only $770 roundtrip with Air Canada.
October 29, 2025 Non-stop from Chicago to the US Virgin Islands for only $242 roundtrip Non-stop flights from Chicago to the US Virgin Islands for only $242 roundtrip with United Airlines.
October 28, 2025 US cities to Manila, Philippines from only $498 roundtrip Cheap flights from US cities to Manila, Philippines from only $498 roundtrip with All Nippon Airways.
October 26, 2025 Non-stop from Chicago to San Juan, Puerto Rico for only $218 roundtrip Non-stop flights from Chicago to San Juan, Puerto Rico for only $218 roundtrip with United Airlines.
October 25, 2025 Non-stop from Baltimore to Chicago (& vice versa) for only $139 roundtrip Non-stop flights from Baltimore to Chicago for only $139 roundtrip with American Airlines. Also works in reverse.
October 24, 2025 Non-stop from Chicago to New Orleans (& vice versa) for only $168 roundtrip Non-stop flights from Chicago to New Orleans for only $168 roundtrip with United Airlines. Also works in reverse.
October 22, 2025 NEW YEAR: Non-stop from Chicago to Palm Springs, California (& vice versa) for only $151 roundtrip Non-stop, New Year flights from Chicago to Palm Springs, California for only $151 roundtrip with United Airlines. Also works in reverse.