May 23, 2025

Quick Hits: Insane Rakuten Deals, an Unfortunate End to the Amex to Alaska Airlines Loophole, and More!

23 minutes

Looking to maximize your points game and stay ahead of the travel curve?

In this extended Quick Hits episode, DeAndre Coke dives into one of the busiest travel news weeks yet. From Rakuten and SoFi points play to Delta’s award rate drops and United’s sleek new Polaris business class suites, there’s something for every traveler. He covers the Hilton Honors devaluation, a limited-time AA award sale, and the end of the valuable Amex-to-Hawaiian-to-Alaska Airlines transfer loophole. Plus, there’s new info on Chase’s Instacart perks, updates on the Zil Money saga, and a reminder that May is prime time for booking summer travel.

Packed with strategy, news, and savings hacks—you won’t want to miss it.

Key takeaways:

Rakuten deals: Huge Amex point earning opportunities—some merchants offering up to 95x points.

SoFi bonus: Opening a new SoFi account with a $500 direct deposit can earn 25,000 Amex points.

Delta award rates drop: Flying Blue redemptions on Delta-operated flights are ~20% cheaper for 2026.

United upgrades: New Polaris Studio Suites will offer luxury in-flight experiences starting in 2026.

Hilton devaluation: Standard award nights at top-tier hotels now cost up to 200,000 points.

American Airlines sale: Over 1 million award seats available from 5,000 miles—book by May 28.

Amex transfer loophole: The Amex-to-Hawaiian-to-Alaska points route ends June 30.

Chase Instacart perks: New $10–$20 monthly credits across many cards, plus free Instacart+ trials.

Zil Money update: The payroll on credit card feature was delayed another month, which is now expected in June.

Book now for summer: Prices for flights and hotels are lower than usual—rebooking could save $$$.

Resources:

Rakuten Referral Link

Shopping Portals Explained (Ep. 49)

Blog: How to Use Shopping Portals to Boost Your Points and Miles

Start here to learn how to unlock nearly free travel

This month’s best current card offers

LTH Online Points & Miles In Depth Course:

Use coupon code “BOLDYGO” for a 50% discount!

BoldlyGo Travel With Points & Miles Facebook Group

Truicity Wealth Management

Thrifty Traveler Premium

Daily Drop Newsletter

Book a Free 30 minute points & miles consultation

This month’s best current card offers

BoldlyGo Travel With Points & Miles Facebook Group

Interested in Financial Planning?

Truicity Wealth Management

Some of Our Favorite Tools For Elevating Your Points & Miles Game:

Note: Contains affiliate/sponsored links

Card Pointers (Saves the average user $750 per year)

Zil Money (For Payroll on Credit Card)

Travel Freely

Point.me

FlightConnections.com

Thrifty Traveler Premium

LTH Online Points & Miles In Depth Course:

Use coupon code “BOLDYGO” for a 50% discount!

Connect with DeAndre Coke:

Instagram: BoldlyGo.world

Website: BoldlyGo.world

YouTube: BoldlyGoWorld

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By DeAndre Coke

4.8

5050 ratings