Layla plans anywhere and moves you toward an Expedia checkout. Winnie plans India specifically, has no inventory to push, and is free forever. For India, Winnie wins.
Acquired by Expedia Group on July 31, 2026. Operates as a standalone brand alongside Expedia.com, Hotels.com, and Vrbo. Absorbed Roam Around in 2024; layla.ai/roamaround is live.
Compared as of September 2026. Legend: yes, no, partial, or coming soon on the Winnie roadmap.
Layla was acquired by Expedia Group in July 2026. Its job now is to move you from chat to an Expedia-family checkout: Booking.com, Skyscanner, Viator, GetYourGuide. That is a real product with real utility, and it is also a real incentive on what the chat recommends. Winnie is independent and has no inventory to push, so the itinerary is the product, not the funnel.
Layla plans the whole world, which means India gets the same generic treatment as everywhere else. Winnie only does India. That difference shows up the moment your trip hits a real Indian edge case: a temple town without on-site hotels, a Himalayan pass closed in your travel month, a train class that sells out 90 days ahead, a state that needs a permit. Winnie was built to know these.
Layla's full experience sits behind $49/year on web, higher on iOS, and reviewers disagree on where the free tier actually ends. Winnie is free forever, no card, no signup for your first plan. Guest mode is the default so you can judge Winnie on the plan itself, not on a paywall.
Winnie treats every refinement as an edit. Add Munnar and Munnar appears, drive times adjust, and Winnie reports what shifted. Nothing regenerates from scratch. That is the difference between a friend who knows your trip and a template engine that starts over.
Layla's live flight and hotel pricing from booking partners is genuinely strong for worldwide trips. If you want a bookable multi-country Europe itinerary or a Southeast Asia loop and you are happy transacting through the Expedia family, Layla is a fine choice. When your trip touches India, come back to Winnie. A specialist wins on its home turf.
For India, Winnie. Layla was acquired by Expedia in July 2026 and now optimises for moving you to a partner checkout. Winnie is independent, India-only, and free forever with guest mode. On India-specific rules like Inner Line Permits, Kedarnath's on-site hotel constraints, and Manali-Leh's winter closure, the specialist wins.
Winnie is free to plan forever, with a guest mode so your first plan does not need a signup. Layla has a free tier plus Premium at $49/year on web (higher on iOS), and reviewers report core features like the full day-by-day plan sit behind Premium.
Not today. Winnie is planning-first. You plan the trip with Winnie and then book on your preferred platform. In-app booking with INR and UPI is on the Month 6 roadmap and will be a convenience layer on top of your plan, not a commission funnel.
Yes, and this is where the India specialism pays off. Winnie plans multi-city inside India with honest drive times, correct train routing, seasonal awareness, and permit lead times. Ask for 'Golden Triangle plus Rishikesh in 10 days' and Winnie plans it end to end.
Winnie. Because it is India-only, Winnie tunes routing, hotel tier, and pacing to the traveller type. A honeymoon plan leans houseboat plus hill station, a family plan reduces travel days, a solo female plan prioritises well-lit stays and daytime transfers.
For trains and monuments, Winnie uses verified fares where the data is available. For hotels, Winnie gives honest tier ranges (budget, mid-range, upmarket) rather than pretending to know a single exact rate. For flights, Winnie surfaces wide ranges plus live booking links.
No, and that is a design choice, not a limitation. Winnie is India-only on purpose because that is what lets us go this deep. For anything outside India, Layla is a reasonable generalist pick.
Both use large language models; Layla has not publicly disclosed which. The difference is what wraps the model. Winnie is a product with India-specific data and rules (train fares, hotel tiers, monument timings, permit lead times) baked into the output. Layla is a worldwide generalist that now pipes chat to Expedia-family checkouts.
Free. No signup for your first plan. India-only, planning-first.
Start planningCompetitor pricing, ownership, and feature scope change often. If you spot something out of date, tell us at hello@trywinnie.com and we will fix it.