Part of this hobby is EARNING points and miles, and the other half is redeeming them. It's fairly "easy" to earn your points and miles - open and credit card, meet the spend, and receive the bonus. Finding the "perfect" award flight is the most difficult aspect in points and miles. It takes skill and patience.
I'm here to give you the tools you need so that you can do this on your own - but you have to spend some time practicing. Run your own practice redemptions now - this way when you are ready to actually book a flight you are more comfortable and know what to look for. Literally, refer to the transfer chart below, log into different airlines and find award flights. You will quickly notice the vast difference in point pricing, or that the same flight on one airline uses more points but lower taxes, and another airline has fewer points but higher taxes. (Hint: United vs. Aeroplan)
Here are a few general tips to get you started:
Don't use your points to book with the bank's portal. The point cost is often much higher and is generally considered a poor redemption. Instead - you will transfer your points to the airline to book. ***Always make sure the flights are available first before transferring.
Open a loyalty account for pretty much every airline and major hotel chain for you and your family. (See award chart below.) Even if you think you will never fly with that airline - open an account anyways because you never know what partner airline you will end up booking with. Accounts often need to be open for at least 3 months in order for the transfer from your CC account to the airline. (Make a spreadsheet that lists out each airline and hotel chain, account # and password for quick reference.)
Learn the transfer partners. See below a great chart from Award Travel 101. It shows the alliance partners, which bank transfers to which airline and so forth. Keep this handy for future reference!
4. Practice! United is one of the easier redemptions. Log into the website, search for the flights you want and click "Book with Miles". I like to open the "30 day calendar" to get a full months view of award space. United is also one of the few airlines that highlight if it is a "saver" award flight.
*Saver flights you can often find on partner airlines for less points, or using a different currency.
5. Prepare to reposition when flying business class. A repositioning flight is where you book a cheap flight somewhere and book an awesome redemption from somewhere else. For example: It is pretty tough to find business-class tickets to Europe from Phoenix. So instead, I usually search out of places that are easy to fly to -- LAX, SFO, DFW, DEN - you get the idea. On Southwest, these flights are often less than $100. Then, I book my point redemption flight from LAX to say Amsterdam (AMS).
**Note: Economy is generally much easier and you will be less likely to have to reposition out of Phoenix depending on the location.
6. Europe is VERY easy to get around to. Say you wanted to visit Paris, but couldn't find any great flight redemptions there. Book your LAX to AMS flight. Hang in Amsterdam for 1-2 days (if you like) and then hop on the train to Paris!
7. Get comfortable booking one-way tickets. You don't have to fly in and out of the same airport. This allows you more flexibility with your travel itinerary, and it is easier to make last-minute changes if needed.
8. You want to understand and look for Saver flights to get the best redemptions! These rates are the cheapest but can be more difficult to find. You will see crazy redemptions such as business class to Europe for 200k points one-way. This is NOT what you are looking for. You should be able to find a business class ticket for 50-65k points each way (or less).
Sweet spot examples include:
Business class from East Coast/Chicago to Madrid on Iberia for 35k off-peak pricing
12K flights using Avios (transfer from Chase to British Airways) to book a Domestic American Airlines Flight
Aeroplan to Central America in Economy for 12,500k points.
9. The best flights are usually booked early -- as in 9-11 months in advance. Different airlines open their award schedule at different times, so you will want to do some research on this.
Here are a few articles and videos to give you some additional insights:
Why Booking One-Way Flights Can Be a Great Redemption Strategy
The 16 “Best of The Best” Ways To Use Your Points & Miles [For Incredible Value]
How to Calculate the Value of a Point or Mile When Redeeming
Understanding the difference between award charts and dynamic pricing
Let me know if you would like some guidance - I'm happy to help give some additional advice with your first redemption. It takes practice, and expect to not find the flight you want on your first shot. I run award searches regularly, until I find the one I am looking for. Sometimes I lock in a hard-to-book hotel without flights and vice versa. There are times when I book a one-way flight and don't book the opposite direction for a month or so. The key point here is to stay flexible.
I love the Expert Flyer tool. I can insert ideal flights and set up award alerts. This way, when a Saver rate becomes available, I will get a notification instead of searching multiple airlines throughout the day. Here is a short article that explains how to use the tool.