Cheap flights, use Skycanner (enter price change alerts In Skyscanner and other websites) and google flights. For the region you intend to fly, choose budget airlines and give you email address to them to get flight sale alerts. Also search those airlines in facebook for alerts.
My ultimate hack/strategy is travel only when it is dirt cheap, this generally means buying 1 to 12 months ahead. Have multiple destinations in mind. This is not for a “time is money person” 20 USD international airfares are needle in a haystack stuff, you need to patient on line and enjoy the thrill of the chase. I'm looking forward to my Manila to Tokyo 4.5 hour return flight that I paid $USD42 including all taxes and fees. Compared to fly next week prices, you pay 1/10th to half price, the reward for being extremely flexible.
Hotels, use Wikitravel and Lonely Planet to find the area of a city to look in. book one night ahead if ur arriving late at night, next morning go and negotiate with the owner/manager of your favorite hotel for one month. The effective daily rate you pay will be around 1/3. Even if you only stay 3 weeks you save. If management does not have a monthly rate, reduce the daily rate, multiply by 30 and offer cash up front.
Happy travels
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