Stop leaving points on the table.

Expert guidance. Smarter redemptions. Better trips.

Award Caddie helps people turn points and miles into the trips they actually want. We work with each client one-on-one, drawing on your points, status, and everyday spending to find the best way to get there. Whether you have a trip in mind or a pile of points and no plan, we handle the strategy so you don't have to.

Book an introductory call

How we help

A traveler working on a laptop in an airport lounge

Your points

You have points and no plan.

We look at what you hold and turn it into a specific trip.

A man at a laptop holding a phone and a credit card

Your spend

You spend a lot and earn too little.

From business purchases to renovations, we show you which cards and programs turn big expenses into points.

A row of airline check-in desks in a terminal

Your itinerary

You have a complicated itinerary and no time.

Multiple cities and tight connections. We do the research and walk you through the best options.

A hand holding a first class boarding pass in front of a departures board

Your status

You're building toward status.

We plan travel around your goals, so every trip moves you closer to where you want to be.

How it works

1
A conversation
Start with a short introductory call. Tell us where you want to go and what you have to work with.
2
A plan
We come back with the best options and walk you through the details.
3
Hands-on support
We guide you from transfer to takeoff, and stay in your corner if plans change along the way.

Every client is different, so every engagement is too. We also book full itineraries, including hotels, transfers, and beyond, and we offer ongoing partnerships for clients who travel often.