May 6, 2026 🔥 Non-stop from Chicago to San Juan, Puerto Rico for only $44 one-way Non-stop flights from Chicago to San Juan, Puerto Rico for only $44 one-way.
April 23, 2026 Chicago to Delhi, India for only $562 roundtrip Cheap flights from Chicago to Delhi, India for only $562 roundtrip with Air France and KLM.
April 21, 2026 SUMMER: Non-stop from Chicago to Portland, Oregon (& vice versa) for only $195 roundtrip Non-stop, summer flights from Chicago to Portland, Oregon for only $195 roundtrip with United Airlines. Also works in reverse.
April 21, 2026 SUMMER: Non-stop from Chicago to San Diego (& vice versa) for only $219 roundtrip Non-stop, summer flights from Chicago to San Diego for only $219 roundtrip with United Airlines. Also works in reverse.
April 10, 2026 Chicago to Algiers, Algeria for only $576 roundtrip Cheap flights from Chicago to Algiers, Algeria for only $576 roundtrip with Turkish Airlines.
March 25, 2026 Chicago to Medellin, Colombia for only $392 roundtrip Cheap flights from Chicago to Medellin, Colombia for only $392 roundtrip with Copa Airlines.
March 12, 2026 Chicago to Honolulu, Hawaii (& vice versa) for only $372 roundtrip Cheap flights from Chicago to Honolulu, Hawaii for only $372 roundtrip with United Airlines. Also works in reverse.
March 8, 2026 Non-stop from Boston to Chicago (& vice versa) for only $115 roundtrip Non-stop flights from Boston to Chicago for only $115 roundtrip with United Airlines. Also works in reverse.
March 8, 2026 Non-stop from Chicago to Fort Lauderdale (& vice versa) for only $147 roundtrip Non-stop flights from Chicago to Fort Lauderdale for only $147 roundtrip with United Airlines. Also works in reverse.