🔥 Chicago to San Juan, Puerto Rico for only $122 roundtrip (Jan-Feb dates)
Cheap flights from Chicago to San Juan, Puerto Rico for only $122 roundtrip with United Airlines.
Flight deals from Chicago - Book cheap flights
Chicago to Spokane, Washington (& vice versa) for only $187 roundtrip (Feb-Mar dates)
Cheap flights from Chicago to Spokane, Washington for only $187 roundtrip with American Airlines. Also works in reverse.
Chicago to Boise, Idaho (& vice versa) for only $117 roundtrip (Nov-Feb dates)
Cheap flights from Chicago to Boise, Idaho for only $117 roundtrip with Alaska Airlines. Also works in reverse.
Chicago or Dallas to Caribbean islands from only $254 roundtrip (Nov-Feb dates)
Cheap flights from Chicago or Dallas to Caribbean islands from only $254 roundtrip with American Airlines.
Chicago to Barranquilla, Colombia for only $395 roundtrip (Oct-Feb dates)
Cheap flights from Chicago to Barranquilla, Colombia for only $395 roundtrip with Copa Airlines.
US cities to Hawaii (& vice versa) from only $353 roundtrip (Oct-Dec dates)
Cheap flights from US cities to Hawaii from only $353 roundtrip with Alaska Airlines. Also works in reverse.
US cities to the Caribbean or Central America from only $149 roundtrip (Nov-Mar dates)
Cheap flights from US cities to the Caribbean or Central America from only $149 roundtrip.
🔥 US cities to Puerto Rican cities from only $157 roundtrip (Sep-Dec dates)
Cheap flights from US cities to Puerto Rican cities from only $157 roundtrip with JetBlue.
Chicago to Juneau, Alaska (& vice versa) for only $286 roundtrip (Oct-Dec dates)
Missed the deal? Become a Secret Flying member to receive alerts to your inbox the moment we publish a flight deal. You'll never miss a Secret Flying deal again. Cheap flights from Chicago to Juneau, Alaska for only $286 roundtrip
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