Flights
Kayak - my go-to! Searches multiple airlines and websites (including Priceline) and allows for "flexible" date searches to help find the cheapest flight available. Also allows you to search for "longest duration" flights -- aka take an extended layover in a new city! (See my blog post on extended layovers here)
Google ITA Matrix - another multiple-airline search engine, powered by Google. With an older interface it's not as easy to navigate as Kayak, but can be very useful for finding cheap flights out of your departure city.
Google Flight Search Map - if you have the urge to just get away to nowhere in particular, this is the site! Use the interactive map to compare prices from your departure city to destinations worldwide. This is how I found my trip to Miami / Haiti / Dominican Republic.
Airline Miles
The Points Guy - very informative, easy to use website on accumulating and using airline miles for reward flights.
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