You Booked the Flights. AI Travel Site From Kayak Co-Founders Wants to Do the Rest
A new AI service backed by some of the bigger names in the travel business aims to bring conversational ease to booking the non-flight parts of your trip: places to sleep, places to eat, and things to do. The founders of Lola, opening for business Tuesday, say they want to bridge the gap between asking an AI chatbot for help with those things and actually booking them. “LLMs do a really good job of answering free-form questions,” said co-founder Steve Hafner, who also co-founded Kayak.
- ▪A new AI service backed by some of the bigger names in the travel business aims to bring conversational ease to booking the non-flight parts of your trip: places to sleep, places to eat, and things to do.
- ▪The founders of Lola, opening for business Tuesday, say they want to bridge the gap between asking an AI chatbot for help with those things and actually booking them.
- ▪“LLMs do a really good job of answering free-form questions,” said co-founder Steve Hafner, who also co-founded Kayak.
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| Original publisher | PCMag |
| Canonical URL | https://www.pcmag.com/news/you-booked-the-flights-ai-travel-site-from-kayak-co-founders-wants-to-do |
| Publication time | Tue, 29 Sep 26 13:00:00 +0000 |
| Retrieval time | 2026-09-29T13:31:21.929Z |
| Last seen | 2026-09-29T13:31:21.929Z |
| Headline source | Publisher (no WeSearch rewrite) |
| Excerpt source | publisher body |
| Excerpt method | First ~120 words (~800 chars) of extracted publisher body, fair-use limited. |
| Summary | WeSearch · cerebras-chat (WeSearch summarizer) |
| Summary source text | contentText |
| Citation coverage | Summary is a WeSearch-generated derivative; primary citation is the original publisher URL. |
| Cluster | iiIgVsRIR2Kn · 1 stories |
| Cluster logic | Grouped by semantic title/content similarity across sources within a rolling window. Same-publisher template collisions are excluded from coverage comparison. |
| Ranking reason | Story pages are not engagement-ranked. Hub feeds use recency, with optional source-diversified chronological ordering (cap consecutive stories per source). No personalized ranking. |
| Publisher visit | Yes — open original |
| Substitutes article? | No — link-out required for full text |
Rights status (four layers)
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| Indexing | May the item be indexed (stored, ranked, made findable)? | Allowed |
| Snippet | May a short excerpt of the publisher's text be shown? | Allowed |
| AI summary | May WeSearch generate its own short summary of the article? | Limited |
| Retrieval / RAG | May the content be exposed for third-party retrieval-augmented generation? | Not asserted |
| Model training | May the content be used to train AI models? | Not asserted |
| Commercial reuse | May the content be reused commercially? | Not permitted |
Basis: Derived from the published RSS/Atom feed. Contact: [email protected]. Reviewed: 2026-07-24.
Opening excerpt (first ~120 words) tap to expand
A new AI service backed by some of the bigger names in the travel business aims to bring conversational ease to booking the non-flight parts of your trip: places to sleep, places to eat, and things to do. The founders of Lola, opening for business Tuesday, say they want to bridge the gap between asking an AI chatbot for help with those things and actually booking them. “LLMs do a really good job of answering free-form questions,” said co-founder Steve Hafner, who also co-founded Kayak. “But where they fall down is once they make you a recommendation.”We’ve seen the transition from chatting with an AI interface to having the AI try to complete a booking at another site become brittle.
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Excerpt limited to ~120 words for fair-use compliance. The full article is at PCMag.
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