Scott's Cheap Flights 🌵 San José del Cabo — $200s/$300s

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There's rarely a bad time to be had in Mexico so the least you can do is get there without breaking the bank. 

The cheapest fares with United do not include a full-size carry-on. It costs $25-$40 each way to upgrade to regular economy if you want overhead bin space, and a checked bag costs $30-$35 each way on all airlines.