AI Hustle Podcast: Google Pushes AI ‘Flight Deals’ Globally, New Travel Features in Search

Episode Date: November 21, 2025
Hosts: Jaeden Schafer and Jamie McCauley

Overview

This episode dives into Google’s recent global rollout of its AI-powered “Flight Deals” tool and the addition of new travel planning features in Google Search. Jaeden and Jamie explore how these tools are transforming the travel booking experience, discuss their personal trial runs, and provide a candid assessment of where Google’s new features succeed, where they fall short, and what this all might mean for travel agents and entrepreneurs.

Key Discussion Points & Insights

1. Google Flights Deal Tool Goes Global

• What’s New:
  • Google’s AI-powered tool now searches across sites to find the cheapest flight deals worldwide.
  • The rollout extends features previously limited to the U.S.
  • Notable: New “Canvas” feature for trip planning/visualization.

2. Personal Experiences & Honest Reviews

• Jamie’s hands-on experience:
  • Jamie helped his mom book flights to Switzerland—secured a $600 round-trip deal, about $200 cheaper than elsewhere.

    “The flight that we found was like $200 cheaper than anywhere else…it really does work.” (Jamie, 01:50)

• Jaeden’s test-drive:
  • Initially found the tool underwhelming:

    “My first experience with it was disappointing, but I probably had too high of expectations…” (Jaeden, 03:28)

  • Found its natural-language search was more limited than hoped.
  • Praised Google Flights for showing transparent price calendars that make deal-finding “never been easier.”

    “I don’t know what people did before that.” (Jaeden, 04:07)

3. Natural Language Search: Potential & Current Limits

• Google’s tool can handle basic, fairly broad natural language requests (e.g., “Help me plan a girls trip to Phoenix with three friends…”)

• Complex itineraries (multiple stipulations, kids, flexible ranges) can overwhelm the system.

  “I said I want to go to Hawaii for the next two weeks with a family of two adults and three kids...it said we couldn’t match your search. Your search might be a bit too complex for our current capabilities...” (Jaeden, 06:37)

4. Comparison with ChatGPT and Expedia Plug-in

• Jaeden tests the same itinerary in ChatGPT + Expedia.

• Finds integrations are not obvious or consistent.

  “It feels like no one has really figured this out…every time a new AI model comes out…everyone uses the book-a-trip demo…and yet here I am struggling to get ChatGPT to search… and Google’s own flight deal is struggling to do it.” (Jaeden, 08:16)

5. The “Canvas” Visual Trip Planner

• New feature lets users visually map out trip segments: flights, hotels, activities across dates.

• Has potential to simplify planning and reduce the back-and-forth of traditional travel booking.

  “You can actually plan out your trip… gives you a visual to help you plan your trip and make all those connections.” (Jamie, 02:40)

6. Vacation Rentals Feature

• Jamie notes Google Search includes a “Vacation Rentals” tab (links to VRBO and Expedia, not Airbnb).
• Observes some quirks:
  • Some links go to unknown third-party sites, not direct booking pages.

  • Not fully reliable for vacation rental entrepreneurs (e.g. properties don’t always show up properly).

    “It had basically any link I would click on…it would go to a third party site that didn’t even have my property…so it’s not actually pulling up the Airbnb link where you can book it.” (Jamie, 09:44)

7. Limitations and "Workarounds"

• The system currently struggles with complex requests, especially those involving children in the party.

• A workaround: remove kids from the search to get results (obviously not ideal!).

  “Pro tip, if you have kids, don’t put them into the flight deal thing. I’m sure you could still go book their tickets, but it’s not going to look for them.” (Jaeden, 10:25)

• These quirks highlight that even top AI travel tools still involve trial-and-error and aren’t “agentic” in the way demos promise.

8. Broader Reflections

• Both hosts see the potential for these AI tools to threaten traditional travel agents—eventually.

• They caution against the hype: even with exciting demos, users will run into random and inconsistent limitations.

  “Perhaps people oversell and overhype the capabilities of their AI models…” (Jaeden, 08:56) “I think eventually it will all work…but for now I think Google Flights is a pretty good tool specifically for flights. I don’t know about planning a whole vacation yet.” (Jamie, 09:35)

Notable Quotes & Memorable Moments

• Success story:
  • “The flight that we found was like $200 cheaper than anywhere else...It really does work.” (Jamie, 01:57)
• On Google flights’ UI:
  • “I don’t know what people did before that.” (Jaeden, 04:07)
• On AI travel hype:
  • “Every time a new AI model comes out…and yet here I am struggling to get ChatGPT to search for two weeks for five people, and Google’s own flight deal is struggling to do it.” (Jaeden, 08:16)
• Pro tip for workarounds:
  • “Pro tip, if you have kids, don’t put them into the flight deal thing...it’s not going to look for them doing that specific search.” (Jaeden, 10:25)
• On current state and future:
  • “I think eventually it will all work, but, you know, I think we’re in the beginning stages of it right now.” (Jamie, 09:35)

Important Segment Timestamps

• [01:50]: Jamie details real-life savings using Google Flights for international travel.
• [02:40]: Overview of the Canvas visual trip planning tool.
• [03:28]: Jaeden’s disappointments & observations with natural language capabilities.
• [06:34]: Live demonstration of complex search breakdown.
• [07:09]: Jamie highlights Google’s foray into vacation rentals.
• [08:16]: Jaeden’s big-picture complaint about AI travel demos and reality gap.
• [09:44]: Jamie points out limitations in Google’s vacation rental integration.
• [10:25]: Jaeden discovers quirks with searching for flights with kids.

Tone & Takeaway

The episode maintains an upbeat, candid, and slightly irreverent tone, with both hosts sharing both victories and frustrations, always focused on practical realities for entrepreneurial listeners. The key message: Google’s new AI travel features are promising and already useful for deal-hunting, but don’t expect seamless “AI agent” experiences just yet—and be ready for some quirky workarounds!