How does upselling work in Chekin?
How does upselling work in Chekin? A host configures a catalogue of offers once from the dashboard. The system then distributes those offers across the online check-in form, the Digital Guidebook, and the Unified Inbox with AI, which proposes offers in context inside guest conversations.
Offers can be the host's own services, the host's own external partners, or partners already pre-integrated by Chekin. The guest pays in one click and payment lands directly in the host's Chekin account. This article walks through how each piece of the system fits together.
The two-part architecture: sources of offers and surfaces of display
Most explanations of Chekin Upselling skip this distinction, which is why the system often sounds more complicated than it is. There are two separate things going on:
- Sources of offers: where the offer comes from (host's own services, host's own partners, Chekin marketplace).
- Surfaces of display: where the guest sees the offer (online check-in form, Digital Guidebook, Unified Inbox AI).
The catalogue is one object, not three. The host doesn't configure separate catalogues per channel; a single offer, created once, propagates across whichever surfaces the host activates.
Sources of offers: three ways to fill the catalogue
1. The host's own services
Anything the host runs in-house: early check-in, late check-out, room upgrade, breakfast, parking, welcome packs, spa amenities, transfers operated directly. The host picks the price, sets the availability window (date range, quantity per day, lead time), and chooses which guest profiles see it.
The host keeps the full price minus the 10% Chekin commission applied only on what guests actually pay for. If a guest doesn't buy, no commission is charged.
2. The host's own external partners
External providers the host already works with: a nearby restaurant, a surf school, a wine cellar, a local masseuse, a private guide. From the FAQ on the Chekin Experiences page: "if you have any agreements with restaurants or companies that offer experiences such as horseback riding, snorkelling and more, you can include it. Setting it up is as simple as adding a photo, text and the price you decide."
Configuration takes three fields: photo, description, price. The host negotiates the deal with the partner outside Chekin. Chekin only processes the guest payment.
3. The Chekin marketplace
A set of partners pre-integrated by Chekin: eSIM data plans, airport transfers, walking tours, and curated local activities. The host activates each one with a single click from the dashboard. No negotiation is needed and no inventory has to be maintained. Commission is paid out automatically to the host's Chekin account on each booking.
Surfaces of display: three places where the guest sees the offer
Online check-in form
When the guest fills in the online check-in, Chekin shows the offers tied to that reservation. This is the highest-converting surface because the guest is already engaged with the booking. Anything tied to arrival timing (early check-in, transfer, welcome pack) belongs here.
Digital Guidebook
Once the check-in is confirmed, the guest opens the guidebook to find Wi-Fi, directions, house rules and local recommendations. The configured offers from the catalogue appear inside the same screen, reaching guests who never read marketing emails. Local experiences from the host's partner network usually convert best on this surface, because guests are already in planning mode while reading the guidebook.
Unified Inbox with AI
This is the surface that changed the most in the 2026 update. The Unified Inbox centralizes WhatsApp, email, SMS, OTA messages and phone calls into one conversation thread per guest. The AI reads each message and matches it against the catalogue to suggest a fitting offer when one exists.
A guest asks "can we leave bags after check-out?" and the AI offers paid luggage storage from the catalogue. A guest writes "we land at 2am" and the AI offers an airport transfer from the Chekin marketplace. When check-out day approaches without an extension request, the AI can proactively propose a late check-out from the host's own services.
The AI replies in natural language and in the guest's own language, based on documents the host uploaded (property manual, house rules, FAQ).
Setup: from zero to live in one session
- Log into the Chekin dashboard. If the host doesn't have an account, the 14-day free trial signs up in under 5 minutes.
- Open the Upselling section in the top menu, between Bookings and Documents.
- Click 'Create Offer'. Choose between a custom offer or one of the pre-built templates (Early check-in, Late check-out, Transportation, Pizza on arrival, etc.).
- Register suppliers if needed. For partner offers, the host first registers the supplier in the left-side menu, then links the offer to that supplier.
- Fill the offer fields: title, description, price, availability window, quantity per day, lead time. The dashboard shows a live mockup of how the offer will look during online check-in.
- Pick the image. The host can upload one or pick from the Chekin image library.
- Set the targeting. Select which properties the offer is available in, and which guest profile sees it (families, couples, business travelers, solo guests).
- Save. From this point on, the offer is live across all three surfaces simultaneously. The host can also copy a direct link to send the offer manually if needed.
- Activate marketplace partners (optional). One click in the marketplace section adds eSIM, transfers, walking tours and curated activities to the catalogue with no further setup.
- Upload the property manual to the Inbox AI (optional but recommended). This is what lets the AI propose offers in context, in the guest's own language. The host uploads PDFs, Word docs or text. The AI is live within 10 minutes.
After setup, the host doesn't need to touch the offer again. Sales, payment and reporting happen on their own.
How the offer reaches the guest: the workflow
| Step | What happens | Where |
|---|---|---|
| Booking confirmation | The reservation enters Chekin from the PMS or OTA | Chekin dashboard |
| Online check-in invite | Guest receives the link to complete check-in | Email/SMS |
| Online check-in form | Guest fills personal data and sees relevant offers | Online check-in surface |
| Check-in confirmed | Guidebook becomes accessible with offers inside it | Digital Guidebook |
| During the stay | Guest writes to host. AI replies and proposes offers when they fit | Unified Inbox AI |
| Payment | Guest pays in one click. No redirect, no second form | Inside the same surface |
| Settlement | Commission deducted, balance lands in the host's Chekin account | Chekin dashboard |
Tracking results: where the host sees what happened
Two places matter for tracking:
- Booking details: the host sees the status of every offer for that reservation. Pending, paid, refunded, awaiting approval.
- Upselling reports: the host sees which offers convert best, which guest profiles buy more, and the total revenue from upselling for any time range.
The data feeds back into the catalogue. If a romantic pack only converts at 2%, the host either rewrites the copy, lowers the price, or retires the offer. If a partner restaurant deal converts at 25%, the host expands that partnership.
FAQ
How does upselling work in Chekin in a nutshell?
The host creates a catalogue of offers once in the Chekin dashboard. The catalogue is shown across three surfaces: the online check-in, the Digital Guidebook, and the Unified Inbox with AI. The AI also proposes offers in context during guest conversations. Payment is processed inside the same flow.
Where do I configure offers in Chekin?
Inside the Chekin dashboard, the Upselling section sits in the top header menu, between Bookings and Documents. From there the host clicks 'Create Offer', picks a template or builds a custom one, fills the fields, sets the availability and targeting, and saves. The offer is live across all three surfaces immediately.
Can I use templates or do I have to build offers from scratch?
Chekin includes pre-built templates for common offers: Early check-in, Late check-out, Transportation, Pizza on arrival, welcome packs, and more. The host can use a template as-is, edit it, or build a custom offer from scratch with photo, description, price and availability rules.
How does the AI in the Unified Inbox decide when to propose an offer?
The AI reads each guest message and matches it against active offers in the catalogue. If a guest asks about luggage storage and a paid storage option exists, the AI proposes it. If check-out approaches and late check-out is available, the AI proposes it. Matching uses message content and stay timing.
Do offers from external partners and Chekin marketplace work the same way for the guest?
For the guest, yes. The catalogue looks identical regardless of source: same photo, description, price and one-click payment. The differences are operational for the host. Own services keep 100% minus a 10% Chekin commission. Partner offers use the host's negotiated price with that partner. Marketplace experiences pay commission from Chekin to the host's account.
Can I set different offers for different guests in Chekin?
Yes. Each offer can be targeted to specific guest profiles using check-in data: couples, families, business travelers, solo guests. A romantic pack appears only to couples. A welcome breakfast for two kids appears only to families. Targeting runs automatically once configured.
How Chekin Upselling fits into the rest of the guest journey
Upselling in Chekin sits inside the same account the host already uses for everything else. The guest data captured during online check-in feeds the segmentation. The PMS sync surfaces the right reservations. Payments run through the existing Chekin infrastructure. The Unified Inbox the host already uses for guest messaging becomes the AI-driven sales surface. Activating upselling doesn't require a second tool or a separate login.
Conclusion
The mechanic behind how upselling works in Chekin is simple once the two layers are separated. The catalogue draws from three sources (own services, host partners, Chekin marketplace) and reaches the guest across three surfaces (check-in, guidebook, Inbox AI).
The AI manages the in-context proposals during messaging; the dashboard shows what converted. Setup takes one afternoon. For property managers and hoteliers who want to know exactly how the system operates before activating it, that's the working picture.
