Unbundling the Platinum Card: How Lola's AI is Rewiring Travel

NEW YORK, NY – September 29, 2026

For the better part of two decades, the digital travel landscape has been defined by a familiar, friction-filled routine: opening a dozen browser tabs, cross-referencing prices, reading endless reviews, and ultimately cobbling together an itinerary through sheer force of will. Metasearch engines brought order to the chaos, but they still required the user to do the heavy lifting. Now, the architects of that very metasearch era are attempting to dismantle it, replacing the search bar with an autonomous agent.

Lola, a newly launched AI assistant for travel and lifestyle experiences, is stepping into this void. Backed by travel behemoth Booking Holdings, the platform is the brainchild of serial entrepreneurs Steve Hafner and Paul English—the very duo who co-founded KAYAK and helped define the modern online travel agency experience. But Lola is not a search engine. It is a conversational AI designed to take users from the initial spark of "What should I do?" directly to "I've booked it," bridging the persistent gap between artificial intelligence recommendations and real-world transactional execution.

The Autonomous Agent: Moving Beyond the Chatbot

The fundamental flaw in the first wave of generative AI travel planners was their inability to act. A user could ask a large language model for a boutique hotel in Paris or a hard-to-get dinner reservation in Manhattan, and the AI would happily oblige with a beautifully formatted list. Yet, the user was still left to navigate the actual booking process manually, often discovering that the AI's suggestions were fully booked or wildly out of budget.

Lola addresses this by integrating directly with the application programming interfaces of its launch partners. These include Booking Holdings' own formidable stable of brands—Booking.com, Priceline, Agoda, KAYAK, OpenTable, and FareHarbor—as well as external luxury and lifestyle services like BLADE, Aero, SeatGeek, GetYourGuide, Nuitee, and Ten Group.

By piping real-time inventory and pricing directly into the conversational interface, Lola transforms from a passive advisor into an active concierge. It understands natural language requests, maintains context through follow-up questions, and, crucially, executes the booking without forcing the user to switch platforms.

"We built Lola to give everyone the advantage of being well connected. The next generation of AI assistants should do more than answer questions. They should understand what you’re looking for, help you decide, and make it happen," said Steve Hafner, co-founder of Lola, in the company's launch announcement.

Unbundling the Luxury Credit Card

Perhaps the most disruptive element of Lola's launch is its business model. While the core conversational discovery and booking engine is available for free, Lola is introducing a tiered subscription model designed to directly challenge the lucrative ecosystem of premium travel credit cards.

For decades, access to elite concierge services, priority dining reservations, and high-end travel perks has been gated behind financial instruments like the American Express Platinum Card, with its nearly $900 annual fee, or the Chase Sapphire Reserve. These cards bundle financial credit with lifestyle access. Lola is attempting to unbundle that access, offering it as a standalone software subscription.

The math presents a compelling alternative for the modern traveler. Lola's Plus tier costs $5 per month, requiring a $60 annual commitment, and offers 10 percent savings on eligible hotels, two-day advance access to sought-after restaurant reservations via ResX, $300 off premium Aero flights, and quarterly access to Ten Group's global concierge service.

The VIP tier, priced at $25 per month or $300 annually, aggressively targets the luxury demographic. It unlocks up to 15 percent savings at four- and five-star hotels, complimentary OpenTable Gold status, five-day advance ResX reservations, and access to $150 BLADE helicopter transfers in New York City. The VIP tier also increases the Aero flight discount to $400 and provides extensive, ongoing access to Ten Group's lifestyle management services.

For a consumer who utilizes even one BLADE transfer or Aero flight a year, the VIP subscription pays for itself, entirely bypassing the need to apply for a high-fee credit card or navigate complex points ecosystems.

"Every partner we add gives members more to choose from and more reasons to be a member," noted co-founder Paul English. "Lola learns what each member likes and searches across hotels, restaurants, events, and experiences to find the options worth their time, with member rates and perks attached. We’re building Lola to be comprehensive, and there are many more partners to come."

A Defensive Moat Against Big Tech Search

To understand why Booking Holdings—a company whose empire is built on traditional search and online travel agency models—is backing Lola, one must look at the shifting tectonic plates of the broader tech industry. The traditional search paradigm, long dominated by Google, is under siege.

Consumers are increasingly turning to conversational AI assistants, such as OpenAI's ChatGPT, Anthropic's Claude, and Meta's Muse, for complex queries. For travel giants, this represents an existential threat. If a general-purpose AI agent becomes the primary interface for travel planning and booking, traditional booking platforms risk being relegated to mere invisible inventory providers, losing their direct relationship with the consumer and their lucrative margins.

Lola is Booking Holdings' defensive moat. By building its own AI-first entry point, the company is attempting to secure its distribution pipeline against Big Tech gatekeepers. Hafner's recent transition from his long-held post as KAYAK chief executive officer to an AI-focused role within Booking Holdings underscores the strategic urgency of this project. Lola keeps users within the broader corporate ecosystem while offering a modernized, frictionless user experience that general-purpose AIs cannot easily replicate without deep, proprietary inventory access.

The Third Act of the Lola Brand

For industry veterans, the name Lola carries a sense of déjà vu. The brand is currently in its third distinct iteration. Paul English originally founded Lola in 2015 as a consumer-facing app that connected travelers with human travel agents via chat. The high operational costs of human-in-the-loop services eventually forced a pivot to corporate travel management, a model that showed promise until the global pandemic decimated business travel.

The company subsequently pivoted to financial technology and expense management before its assets and team were quietly acquired by Capital One in late 2021. The fact that English and Hafner have repurchased the domains and resurrected the brand for this new Booking-backed venture speaks to their enduring belief in the core premise: conversational travel is the future.

What makes this third act different is the underlying technology. In 2015, the natural language processing capabilities required to fully automate a travel concierge simply did not exist. Today, advanced large language models paired with Booking Holdings' massive repository of live inventory make the autonomous agent a viable reality, eliminating the crippling labor costs that doomed the first iteration of the brand.

The Promise of Unbiased Discovery

As Lola enters the market, its most ambitious claim may not be its technological prowess, but its algorithmic neutrality. The company explicitly states that its search results and recommendations are "strictly unbiased and uninfluenced by advertising, vendor payments, or sponsored placement."

In an era where digital real estate is routinely auctioned to the highest bidder, and where "sponsored" tags clutter nearly every commercial search result, a truly neutral discovery engine would be a radical departure. Lola argues that its subscription revenue model frees it from the need to monetize user attention through advertising, allowing the AI to prioritize the consumer's actual preferences.

Whether Lola can maintain this purity while operating under the umbrella of a publicly traded travel conglomerate remains to be seen. However, the proposition itself—a travel assistant that works for the user rather than the advertiser, executing complex bookings with a single conversational prompt—represents a compelling vision for the future of digital commerce. By merging the conversational ease of modern AI with the tangible perks of a luxury lifestyle membership, Lola is not just answering the question of where to go next; it is fundamentally rewriting how we get there.