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Google is officially getting deeper into the points-and-miles world, and Ed and Richard have plenty of questions.

Google is adding travel functionality to AI Mode that can search for points-and-miles availability directly from participating airlines and hotel programs. Initial integrations include Alaska, Hawaiian, American, Choice, Hilton and Wyndham, with Flying Blue, Hyatt, LATAM and Lufthansa among those expected to follow. And the results can be fast—Richard gets award pricing back almost instantly during the show.

But fast doesn't necessarily mean accurate.

Ed puts the new functionality through a series of tests and finds incorrect Hilton award prices, missing hotels, problems with dates and days of the week, and incomplete results. Richard gets Google to find an Alaska Mileage Plan redemption on American—but only after specifically asking about it, and even then Google provides the wrong partner booking fee. They also conduct a live experiment looking for Marriott award availability during Atlanta Braves home games, with some interesting results.

So, is Google AI ready to replace dedicated award-search tools? Not yet. But Ed and Richard agree that if Google can make the data more reliable, the ability to ask a broad question like "Show me every date in October when I can fly this route for 7,500 miles" could become extremely useful.

Richard also breaks down Bilt's new partnership with Blacklane, which allows members to book the chauffeur service directly through Bilt and use Bilt Cash or points toward rides. He explains why a premium airport pickup can be particularly valuable at airports where rideshare pickup is a hassle—and acknowledges that the convenience comes at a price.

Plus, a $10 Uber Eats order somehow becomes a $29 order, the guys discuss air traffic controllers reportedly leaving work early before a fatal airport accident, and Ed celebrates a very points-and-miles-specific parenting achievement.

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✈️ What We Cover in This Episode

  • ✈️ Google AI enters the award-search game

    • Searching airline and hotel awards through AI Mode
    • Direct integrations with travel programs
    • Near-instantaneous results
    • More airlines and hotels coming soon

    ✈️ Can you trust the results?

    • Incorrect award prices
    • Missing hotels and flight options
    • Wrong partner-booking fees
    • Google failing to catch contradictory date information
    • Why knowing the right question to ask still matters

    ✈️ A live Google AI award-search experiment

    • Searching Marriott availability around Braves home games
    • A $700+ hotel room versus 48,000 Marriott points
    • Where Google got the answer right—and where it didn't

    ✈️ Could Google replace award-search tools?

    • The potential of flexible natural-language searches
    • Why accuracy needs to improve first
    • Where dedicated tools still have the advantage

    ✈️ Bilt adds Blacklane

    • Booking chauffeur service through Bilt
    • Using Bilt Cash and Bilt Points
    • Airport pickups without rideshare roulette
    • Richard's experiences testing Blacklane
    • Convenience versus cost

    ✈️ When a $10 food order becomes $29

    • Uber Eats fees
    • A new marketplace fee
    • Small-order fees
    • The economics of delivery apps

    ✈️ Air traffic controllers and "early shove"

    • Two controllers reportedly leaving early
    • The difference between scheduled staffing and actual staffing
    • Why aviation accidents rarely have a single cause
    • Building systems that account for human behavior

    ✈️ Ed's lifetime points-and-miles achievement

    • His daughter gets approved for the Chase Sapphire Preferred
    • Building credit with authorized-user accounts
    • Helping young adults establish credit
    • Using rent reporting as another credit-building tool
⏱️ Episode 452 Timestamps

2:07 – Marriott stays not posting and an MGM booking trick

8:34 – Google brings points-and-miles searches to AI Mode

10:38 – Richard tests Google's award search live

15:05 – Wrong prices, missing results and Google's accuracy problem

18:30 – Live test: finding a Marriott award during a Braves home game

22:49 – Would Ed and Richard actually use Google AI to book travel?

24:14 – Bilt's new Blacklane partnership

28:52 – How a $10 Uber Eats order turns into $29

30:50 – Air traffic controllers, "early shove" and airport staffing

36:06 – Ed's lifetime achievement: his daughter gets a Chase Sapphire Preferred

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