Flexible travel date airfare search
Some airlines and sites have very useful flexible travel date tools. Among airlines, JetBlue, United, Southwest; for third party sites, Kayak and Google Flights are best. On United.com check the "my dates are flexible" box and choose a length of stay. On Kayak, register your email address and select "Show flexible dates"; search the "Southwest Shortcut" and "JetBlue best fare finder."
You might not need travel insurance
Your credit card might already have free, built-in travel insurance up to $5000 per trip for the most common reasons people use insurance, which include canceling before or during a trip due to illness or injury, and lost or delayed baggage. The Chase Sapphire card, United Explorer Card, and some Citibank Aadvantage cards offer the best protection.
Check for price drops after you book
After you pay for an airfare or a hotel, the price may have dropped, but most people never check. You can get either cash or a credit for future travel if you know how. Yapta.com is useful for airline tickets, Tingo.com for automatic refunds on hotel rate price drops.
Air+hotel really can save money. But not always
You've seen those package prices from tour companies and airlines. But how do you know if they're a deal? Sometimes a quick search will give you a very convincing answer. Recently British Airways had airfare plus 5 nights hotel to Dublin for around $750 per person for fall travel.
But airfare alone was $900 or more. A no-brainer.
Heading to Europe? Focus first on crossing the Atlantic cheaply
Fares to Amsterdam might be $1500 round-trip. But Frankfurt? $799 recently on Singapore Airlines from New York, even for summer travel. Frankfurt to Amsterdam? $100 round-trip by train or plane. Think of it as two cities for less than one. Check out under-the-radar airlines such as Norwegian.com, Condor.com and Wowair.com, all of which sell super-discounted tickets from the U.S. to Europe (example: a recent deal on Norwegian to Copenhagen, early August travel, for $615 round-trip nonstop).