✈ Lessons From My ChatGPT Travel Itinerary, Flight Cancellations Ease & More Daily News From TPG ✈

Also: How I got a 45% return on a Hyatt stay in Barcelona

November 15, 2025 View in browser         TOGETHER WITH     TOGETHER WITH

Does the house always win? by Ben Smithson, Senior writer Could artificial intelligence replace hours of travel research? I put it to the test on a last‑minute weekend in Las Vegas — and the results were part jackpot, part bust. Where AI triumphed Time-saving planning: ChatGPT produced an easily digestible "AI-tinerary" within seconds, complete with dining, sightseeing and even a handy map. Brilliant hotel comparisons: Since I was redeeming Hilton Honors points, it compared and ranked Hilton properties, recommending the Conrad Las Vegas at Resorts World for its lively casino energy and Strip location — and I loved my stay there. Helping me save money: ChatGPT found happy hours and sensibly priced dining options, and even reminded me to use my $50 daily Hilton Honors Diamond food-and-beverage credit right after check-in, which was great to keep a rein on costs in an increasingly expensive destination. Where it stumbled Not considering major events: My leisurely day trip to hike the beautiful Valley of Fire State Park coincided with a massive music festival which unexpectedly turned the rental car collection into chaos, and there was no indication in my itinerary of this nearby event. Always suggesting ride-hailing services: ChatGPT doubled down on suggesting ride-hailing services for all short hops that were better suited to walking, where I risked missing unforgettable scenic sunset strolls along the Strip, a must-see for a first-time visitor like myself. Too structured for Sin City: While a ChatGPT itinerary would work great for solo travel or in destinations where punctuality and structure are key, I had the most fun in Las Vegas when I threw caution to the wind and let the night take its course. I would definitely use AI again to plan travel, but would not rely on it for every decision. Ultimately, leaving some flexibility for spontaneous fun rather than following every instruction to the letter is a more preferable way to travel. Want to know more? Check out these resources: I used ChatGPT to plan a Las Vegas trip: Here’s what worked and what didn’t The best hotels in Las Vegas for a Sin City getaway My weekend at the Las Vegas Hilton at Resorts World How buying points saved me $700 at the Conrad Las Vegas at Resorts World The latest attraction in Vegas? Dynamic pricing at hotel lobby shops Hertz rolling out AI rental car inspections: Consumer protection or a new way to charge for damage? Posts in this newsletter contains references to products from one or more of our advertisers. We may receive compensation when you click on links to those products, and this may impact how or where they appear. For an explanation of our Advertising Policy, visit this page. Photo Credit: MACKENZIE ROCHE/THE POINTS GUY.

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Today's top stories Shutdown recovery: FAA will only require airlines to cancel 3% of flights this weekend The FAA reduced its requirement by half on Friday as air travel continued to recover after the government shutdown. Read more Poll: Many Americans worried about travel post shutdown cancel or change holiday plans As much as 40% of holiday travelers considered or made changes to their flight; many are concerned about airline safety. Read more Chase adds new welcome bonus restrictions to its no-annual-fee business cards Chase has introduced new welcome bonus restrictions for the Ink Business Cash and Ink Business Unlimited cards. Read more How I got a 45% return on a Hyatt stay in Barcelona by stacking promotions Learn how I stacked World of Hyatt promos, elite perks and the right card for big hotel savings. Read more Marriott Bonvoy elite status 'soft landing' policy: How to requalify for status If you didn't requalify for your Bonvoy status last year, Marriott will give you the status just below your expiring tier. Read more

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