Once upon a time travel agents helped passengers book their airline tickets and consulted on hotels. That’s now really just something that’s available for high end bookings. And it’s a shame, because you just don’t very good advice from Expedia.

Twelve to fifteen years ago I expected Google Travel to step into the void. They already know so much about you and that’s only increased. From e-mail to location, they know where you go already and what kind of travel you choose. And yet, that never really happened, despite an incredible head start in AI.

Not all travel agents were very good, but there’s a huge opportunity to take AI and offer really great, customized advice – where should you stay? What flights should you take? How long is long enough for a connection, say, in Chicago or Detroit in winter? And does it change based on how many flights per day the airline operates on the route?

One entrant into this space is Gondola.ai, which I first read about at Frequent Miler which heartily endorsed their hotel award search tool.

Gondola.ai is an AI-powered hotel search and booking platform that compares cash and points rates, provides personalized recommendations, and tracking loyalty program balances.

You earn rebates on booking hotel stays through them – even though they are just passing you through to the chain’s website to complete the reservation. And they do a nice job helping you compare hotel redemption options swiftly.

• Gondola allows users to search for hotels across various loyalty programs, displaying both cash and points prices, along with cents-per-point valuations. This facilitates direct comparisons across different programs.

• By analyzing past stays and preferences, Gondola suggests hotels that align with a user’s travel history and loyalty statuses.

• Users can link their email accounts to automatically import and track loyalty program balances, streamlining the management of multiple programs.

• Gondola monitors booked stays and notifies users of any price reductions, allowing for potential rebooking at lower rates. (They don’t have award availability alerts, though.) They help you rebook when prices drop.

• Bookings made through Gondola can earn users up to 3% back towards future bookings.

I really like the way they let you sort search results by point value, rather than just point cost or cents per point. Detailed information provided for each hotel, including typical cash and point price ranges, is really useful.

For instance, it doesn’t just know that getting over 6 cents per point with Hyatt is a good deal – 1 cent per Hilton point is fantastic redemption value. (And the show you both the prevailing room rate and the price inclusive of tax, because you’re saving on taxes when you redeem points, too.)

The real power and potential comes from Gondola getting to know you. You can link your email and it’ll learn all about your travel preferences in order to guide your bookings going forward. This isn’t something everyone will do, and isn’t something you need to do in order to book hotels or use their award search tool.

• They tell me they only see travel reservations (domains like @united.com, @marriott.com, etc.)
  
• They do not store any email (or share data)
  
• And you can delete your account and data
  
• Linking email is optional, but the AI features are where the real potential lies.

During signup I chose to ‘track points manually’ and not give them access to my email… yet.

So I’m covering this right now because they’re offering an a promotion for 5% Gondola cash back (on top of existing hotel loyalty + credit card spend points) to anyone who books three stays in 30 days. (You pick when the 30 days starts.)

Their pitch is that they help you use your points and use them more effectively, and that you save time going to separate hotel program websites to run parallel searches. Honestly I think they undersell themselves here because its the tailored recommendations, if they get that right, that will really add value (to consumers, and to them). They aren’t just recommending hotels that give them the best margin – they look at where you’ve chosen to stay before and suggest properties offering the most value that are most like those.

And they work to make bookings eligible for hotel loyalty program credit, status-earning and status benefits so that their rebates for future bookings are layered on top. They’re booking directly with the chain, and you can even manage your reservations through your hotel program account. Where this applies, and they’re offering the same rates, a 3% rebate is a no-brainer.

But even if you don’t use their AI learning, and you don’t use them for booking, they’re still a useful hotel award search tool for comparing hotel points options across chains quickly and easily, where you can sort your options based on points value (and not just number of points, since those aren’t directly comparable across chains).