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Getting the most out of ClearSkies Essentials Advisor Concierge plan

Concierge is built around ongoing strategy, not one-off decisions.

Share upcoming travel early — we plan best with time
Keep all requests within the dashboard for continuity
Lean on ClearSkies for structure, not just execution
Getting the most out of ClearSkies Essentials Advisor Concierge plan

Advisor works best when you use it before you commit points.

Bring decisions early — before transferring or booking
Include screenshots or specific options when requesting input
Focus on 1–2 strong options rather than broad searches
Getting the most out of ClearSkies Essentials Advisor Concierge plan

ClearSkies Essentials is designed to help you think differently about points — not just use them.

Start with the core frameworks (cash vs points, transfer partners)
Review case studies before making a booking decision
Join the webinars for live Q&A
Explore Your Recent Guidance & Strategy Blueprints
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Newly Added
Business Cards – The Most Overlooked Points-Earning Opportunity
Webinar
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Webinars
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INSTRUCTIONAL Hyatt Transfer Calculator
Video
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Foundations
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Yours, Mine and Ours
PDF
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Checklists
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Solving for the Group, Not the Airline
PDF
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Case Studies
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Recent Member Wins
70,000 points for QSuite business class to Doha
A client planning a South Africa journey navigated Qatar's new restrictive booking to secure two long-haul QSuite seats at saver-level pricing—turning points into an experience that would have been prohibitively expensive to purchase with cash.
+100,000 points from a card she’d already ruled out.
An experienced points user assumed another Chase Ink bonus was off the table. We tested that assumption before moving on to the next card in her strategy. Approved: +100,000 Ultimate Rewards. The opportunity wasn’t a card she didn’t know about—it was a better sequence.
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Foundations

INSTRUCTIONAL Hyatt Transfer Calculator

Here is a quick overview of why we created the Hyatt calculator and how it is designed to work

INSTRUCTIONAL Hyatt Transfer CalculatorHere is a quick overview of why we created the Hyatt calculator and how it is designed to work
Illustration of a woman with a headset appearing on a large curved computer screen, surrounded by six smaller faceless people in business attire, each with speech bubbles, depicting a virtual meeting or webinar.
Webinar

Webinars

Business Cards – The Most Overlooked Points-Earning Opportunity

Learn why business credit cards are one of the fastest ways to build transferable points.

Business Cards – The Most Overlooked Points-Earning OpportunityLearn why business credit cards are one of the fastest ways to build transferable points. Webinars
Illustration of a woman with a headset appearing on a large curved computer screen, surrounded by six smaller faceless people in business attire, each with speech bubbles, depicting a virtual meeting or webinar.
Webinar

Webinars

There Is No Perfect Redemption

A framework for making smarter travel decisions when real-world constraints replace perfect theoretical value.

There Is No Perfect RedemptionA framework for making smarter travel decisions when real-world constraints replace perfect theoretical value.Webinars
Illustration of a woman with a headset appearing on a large curved computer screen, surrounded by six smaller faceless people in business attire, each with speech bubbles, depicting a virtual meeting or webinar.
Webinar

Webinars

Booking Channels — Why the First Option Is Rarely the Best

Learn how different booking paths can produce dramatically different outcomes for the exact same trip.

Booking Channels — Why the First Option Is Rarely the BestLearn how different booking paths can produce dramatically different outcomes for the exact same trip.Webinars
Yours, Mine and Ours
PDF Guide
PDF Guide

Checklists

Yours, Mine and Ours

A quick-reference guide to loyalty programs that let you pool, share or stretch rewards across family members, households and other eligible travelers.

Yours, Mine and OursA quick-reference guide to loyalty programs that let you pool, share or stretch rewards across family members, households and other eligible travelers.Checklists
Solving for the Group, Not the Airline
PDF Guide
PDF Guide

Case Studies

Solving for the Group, Not the Airline

A real-world Japan award strategy showing why splitting a group across airlines can sometimes produce a better trip than waiting for the “perfect” award.

Solving for the Group, Not the AirlineA real-world Japan award strategy showing why splitting a group across airlines can sometimes produce a better trip than waiting for the “perfect” award.Case Studies
Think Beyond the $200 Amex Airline Incidental Credit
New
PDF Guide
PDF Guide
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Advanced Strategies

Think Beyond the $200 Amex Airline Incidental Credit

A smarter way to think about the Amex Business Platinum airline credit—and why the 35% Pay with Points rebate may matter more than using every dollar of the incidental credit.

Think Beyond the $200 Amex Airline Incidental CreditA smarter way to think about the Amex Business Platinum airline credit—and why the 35% Pay with Points rebate may matter more than using every dollar of the incidental credit.Advanced Strategies

Advanced Strategies

When a Bad Transfer Is Actually a Great Deal

Why a terrible transfer ratio can still be the right move when you evaluate points based on the problem they solve—not the ratio on the screen.

When a Bad Transfer Is Actually a Great DealWhy a terrible transfer ratio can still be the right move when you evaluate points based on the problem they solve—not the ratio on the screen.Advanced Strategies

Advanced Strategies

The Citi SUB Timing Window

How Citi’s welcome-offer language can create a narrow opportunity to earn multiple bonuses—and the strategic costs to consider before using it.

The Citi SUB Timing WindowHow Citi’s welcome-offer language can create a narrow opportunity to earn multiple bonuses—and the strategic costs to consider before using it.Advanced Strategies

Foundations

The Problem With Using Points for Upgrades

Why points upgrades can create more uncertainty and less value than directly booking the premium cabin you actually want.

The Problem With Using Points for UpgradesWhy points upgrades can create more uncertainty and less value than directly booking the premium cabin you actually want.Foundations
Retained Points Value: Why Paying Cash Can Be the Best Redemption
PDF Guide
PDF Guide

Case Studies

Retained Points Value: Why Paying Cash Can Be the Best Redemption

A real-world Cabo booking that shows why spending more cash today can sometimes leave your overall travel balance sheet stronger.

Retained Points Value: Why Paying Cash Can Be the Best RedemptionA real-world Cabo booking that shows why spending more cash today can sometimes leave your overall travel balance sheet stronger.Case Studies
When a Card Is Worth Its Annual Fee — But Still Worth Closing
PDF Guide
PDF Guide

Foundations

When a Card Is Worth Its Annual Fee — But Still Worth Closing

Why positive annual-fee math doesn’t automatically make a card a keeper—and the portfolio-level questions to ask before renewing.

When a Card Is Worth Its Annual Fee — But Still Worth ClosingWhy positive annual-fee math doesn’t automatically make a card a keeper—and the portfolio-level questions to ask before renewing.Foundations
Timing Your Way to Southwest Companion Pass
PDF Guide
PDF Guide

Advanced Strategies

Timing Your Way to Southwest Companion Pass

How to coordinate Southwest card applications, welcome bonuses and point-posting dates to potentially unlock nearly two years of Companion Pass.

Timing Your Way to Southwest Companion PassHow to coordinate Southwest card applications, welcome bonuses and point-posting dates to potentially unlock nearly two years of Companion Pass.Advanced Strategies
Create Your “Don’t Forget This” System
PDF Guide
PDF Guide

Foundations

Create Your “Don’t Forget This” System

A simple system for keeping SUB deadlines, expiring rewards and card credits from slipping through the cracks.

Create Your “Don’t Forget This” SystemA simple system for keeping SUB deadlines, expiring rewards and card credits from slipping through the cracks.Foundations
Alliance Inventory Is Not Equal
PDF Guide
PDF Guide

Foundations

Alliance Inventory Is Not Equal

Understand why searching one airline partner isn't the same as searching an entire alliance.

Alliance Inventory Is Not EqualUnderstand why searching one airline partner isn't the same as searching an entire alliance.Foundations
Booking Channel Strategy – Hyatt vs. FHR
PDF Guide
PDF Guide

Case Studies

Booking Channel Strategy – Hyatt vs. FHR

Compare two booking paths for the same Hyatt stay and see how credits changed the outcome.

Booking Channel Strategy – Hyatt vs. FHRCompare two booking paths for the same Hyatt stay and see how credits changed the outcome.Case Studies
How to Think About Large Expenses
PDF Guide
PDF Guide

Foundations

How to Think About Large Expenses

Turn unavoidable expenses into meaningful opportunities to build travel rewards.

How to Think About Large ExpensesTurn unavoidable expenses into meaningful opportunities to build travel rewards.Foundations
Glossary of Terms
PDF Guide
PDF Guide

Foundations

Glossary of Terms

Your quick-reference guide to the language of points, miles, and award travel.

Glossary of TermsYour quick-reference guide to the language of points, miles, and award travel.Foundations
Portal Convenience vs. Transfer Partner Strategy
PDF Guide
PDF Guide

Case Studies

Portal Convenience vs. Transfer Partner Strategy

Compare the easiest redemption with the one that created the better travel experience.

Portal Convenience vs. Transfer Partner StrategyCompare the easiest redemption with the one that created the better travel experience.Case Studies
Why the Best Hyatt Booking May Not Be a Hyatt Transfer
PDF Guide
PDF Guide

Advanced Strategies

Why the Best Hyatt Booking May Not Be a Hyatt Transfer

Discover why the strongest transfer partner isn't always the strongest booking decision.

Why the Best Hyatt Booking May Not Be a Hyatt TransferDiscover why the strongest transfer partner isn't always the strongest booking decision.Advanced Strategies

Advanced Strategies

Booking Channel Strategy – Mileage vs. OTA Cash Booking

See how the booking channel — not the flight itself—changed the overall value of the redemption.

Booking Channel Strategy – Mileage vs. OTA Cash BookingSee how the booking channel — not the flight itself—changed the overall value of the redemption.Advanced Strategies
Don't Let Hotel Loyalty Cost You
PDF Guide
PDF Guide

Foundations

Don't Let Hotel Loyalty Cost You

See how the same hotel stay required less than one-third the points through a different booking strategy.

Don't Let Hotel Loyalty Cost YouSee how the same hotel stay required less than one-third the points through a different booking strategy.Foundations
Loyalty Shouldn't Trump Research
PDF Guide
PDF Guide

Foundations

Loyalty Shouldn't Trump Research

Learn when loyalty programs create value — and when they quietly reduce it.

Loyalty Shouldn't Trump ResearchLearn when loyalty programs create value — and when they quietly reduce it.Foundations

Case Studies

Hawaii for 4 During Peak Summer Travel

Learn how thoughtful trip structure can unlock better award outcomes when availability is limited.

Hawaii for 4 During Peak Summer TravelLearn how thoughtful trip structure can unlock better award outcomes when availability is limited.Case Studies
What to Check Before Closing a Credit Card
PDF Guide
PDF Guide

Checklists

What to Check Before Closing a Credit Card

Protect your points, benefits, and future opportunities before cancelling a card.

What to Check Before Closing a Credit CardProtect your points, benefits, and future opportunities before cancelling a card.Checklists
What to Check Before Applying for a Credit Card
PDF Guide
PDF Guide

Checklists

What to Check Before Applying for a Credit Card

Maximize sign-up bonuses while avoiding common application mistakes.

What to Check Before Applying for a Credit CardMaximize sign-up bonuses while avoiding common application mistakes.Checklists
What to Check Before Booking Through a Portal
PDF Guide
PDF Guide

Checklists

What to Check Before Booking Through a Portal

Compare booking options before using a credit card travel portal.

What to Check Before Booking Through a PortalCompare booking options before using a credit card travel portal.Checklists
What to Check Before You Move Points
PDF Guide
PDF Guide

Checklists

What to Check Before You Move Points

Avoid costly mistakes before transferring points to airline and hotel loyalty programs.

What to Check Before You Move PointsAvoid costly mistakes before transferring points to airline and hotel loyalty programs.Checklists
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New
PDF Guide
Calculator
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Foundations

ClearSkies Card + Credits Tracking Template

ClearSkies Card + Credits Tracking TemplateFoundations
New
PDF Guide
Calculator

Foundations

ClearSkies Hyatt Transfer Optionality Calculator

ClearSkies Hyatt Transfer Optionality CalculatorFoundations