Cash vs. Points
You already know how to evaluate a cash price. Now you need to know where to actually find those prices — because most people are searching in a way that limits what they see.
Three tools. Each does something different. Together they answer every question you'll have before booking a cash flight.
Go to flights.google.com. This is where every flight search starts.
Most people use Google Flights like a basic search engine — type in a destination, pick dates, compare prices. That works. But there's a lot more here.
Click Explore instead of entering a destination. Type in your home airport, leave the destination blank. What you get is a world map showing prices to hundreds of destinations from where you live right now.
This changes the question you're asking. Instead of "how much is Paris?" you're asking "where can I go for under $X?" Completely different question. Much better answers. Some of the best trips happen because someone opened the Explore map without a destination in mind and found somewhere they hadn't considered at a price that cleared the bar.
Once you have a route in mind, open the date grid. You'll see exactly how the price changes day by day across the month. Flying Tuesday instead of Friday can save $150-200 on the same route. The green cells are cheapest. Date flexibility is one of the highest-leverage moves available to you — worth more than almost any other optimization.
If your dates aren't fixed, Google lets you search by trip length (weekend, 1 week, 2 weeks) across a range of months without committing to specific dates. This is how you find the cheapest window for a trip you're planning months out.
Set a price alert on any route you're watching. Google emails you when the price drops. You don't have to keep checking — it tells you.
"Search on Google Flights. Book direct with the airline." Not through Google. Not through any third party. Direct.
You want to be the airline's customer — not a third-party booking's customer — so that if anything changes, you have full control. Changes, cancellations, rebookings all go through the airline directly when you book direct.
Go to kayak.com/explore.
Kayak Explore works similarly to Google's map view but with different filtering options worth knowing about. Enter your departure city, set a budget, and it shows you every destination reachable within that range right now.
The filters here are useful: you can narrow by trip type (beach, family, romantic, outdoors, foodie), flight duration, stops, and even visa requirements. If you're planning a family trip and want to filter to beach destinations under a certain budget with no more than one stop, Kayak Explore does that in seconds.
Use Kayak Explore when you want to plan around what's actually cheap rather than forcing a destination into a budget. You might find somewhere you hadn't considered — at a price that makes the cash/points decision easy.
Same rule applies: search here, book direct with the airline.
Go to flightconnections.com.
This one isn't a price tool at all. It's a route tool.
Click on any airport and it shows you every destination reachable from there, on every airline, with every connection option. Your home airport may not fly direct to where you want to go. FlightConnections tells you which hub gets you there — and which airline operates that route.
This matters for two reasons:
First, routing yourself through a different hub sometimes opens up better prices and better airlines. A $400 direct flight from your regional airport to Europe might become a $240 flight if you drive 90 minutes to a major hub and fly from there instead.
Second — and this becomes more important as you build your points strategy — knowing which routes exist on which airlines tells you which loyalty programs are worth having. Before you search for award availability, you want to know your routing options. FlightConnections answers that question in about 30 seconds.
For any trip:
Run the Explore map if you're flexible on destination. Check the price calendar if you're flexible on dates. Set an alert if you're not ready to book.
When you want to see what's cheap across many destinations, or filter by trip type or budget.
When you need to understand routing, find a hub, or know which airlines fly a particular route.
And always: book direct with the airline.
Find a real deal on a route you care about. Open Google Flights, run the Explore map from your home airport, check the price calendar on a route that interests you, and identify the best window. Then note where you'd book it.
You don't need to book anything. Just run the search with intention. Once you've done it once on a real route, the workflow becomes automatic.