Automate Basics

Calendly vs Chili Piper

Calendly or Chili Piper? Here is how they compare on price, free plan, platforms and the jobs each does best, from each vendor's own pages.

Compiled by · Facts checked 21 October 2026

Compared on
Calendly

Free plan · from $10/seat/mo

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Chili Piper

From $1,250/mo

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What it isBooking-link scheduler with routing forms, Stripe and PayPal payments, and AI add-ons for notes and emailInbound lead routing and instant meeting booking for B2B sales teams, on annual contracts from $15,000 a year
Free planYesNo
Cheapest paid plan$10/seat/mo billed annually (Standard)Calendly pricing$1,250/mo billed annually (Routing & Scheduling)Chili Piper pricing
What it coversUnlimited event types, multiple calendar connections, automations and reminders, HubSpot and Mailchimp, Stripe and PayPal payments. Seats are needed only for people who connect calendars and host meetings, not for invitees.$15,000 a year, billed annually; 15 seats included, then $45 per seat a month; 45,000 AI credits a year. Multi-year contracts get 15% (2 years), 25% (3 years) or 40% (4 years) off.
Free trial14-day free trial; the account then moves to the Free planNone stated
PlatformsWeb, iOS, Android, Chrome extension, APIWeb, API
Integrations (vendor's figure)100+ integrations, including Zoom, Google Calendar, Outlook, Salesforce, HubSpot, Slack, Stripe, PayPal and ZapierSalesforce, HubSpot, Google and Outlook calendars, Slack, Microsoft Teams, Marketo, 6sense, Bombora, Gong Engage, Salesloft, Outreach, Clay, Apollo and ZoomInfo
Open sourceNoNo
Made byCalendly LLCChili Piper, Inc.

Choose Calendly if…

  • You want a free plan: Chili Piper does not have one.
  • You want a mobile app (iOS and Android).
  • The job is sharing a booking link so clients and prospects pick a free time.
  • The job is taking payment when someone books a session.

Choose Chili Piper if…

  • The job is booking demo requests the moment a web form is submitted.
  • The job is routing inbound leads to the right rep in Salesforce.

Still weighing it up?

If neither is quite right, Calendly and Chili Piper are also compared with their other rivals: Calendly vs Cal.com, Calendly vs Acuity Scheduling and Calendly vs Microsoft Bookings.

To see them doing real work, read Send a Feedback Survey After a Calendly Meeting Ends and Add a Zoom Link Automatically to Calendly Bookings.

What Calendly does

  • Booking links and pages with event types, buffers, daily limits and custom availability
  • Connects Google, Outlook and Microsoft calendars to avoid double bookings
  • Automated email and text reminders, and follow-ups
  • Payment at booking through Stripe or PayPal, on Standard and above
  • Round-robin and team scheduling, with routing forms that qualify and route leads, on Teams
  • Notetaker: recordings, transcripts, meeting recaps and draft follow-up emails (Plus plans)

Watch out for

  • Free plan: 1 event type and 1 calendar connection, with no payments
  • Round robin, team scheduling and routing forms need Teams, from $16 per seat a month billed yearly
  • Notetaker and Callie come only with the Plus plans, are available only in English, and Callie is in beta

What Chili Piper does

  • Qualifies, routes and books meetings straight from web forms, including HubSpot, Marketo and Pardot forms
  • Round robin with weighting, meeting limits and fair distribution across products
  • Routes any standard or custom Salesforce object, with fuzzy lead-to-account matching
  • Instant phone or video connect from forms, and live handoffs from SDRs to account executives
  • ChiliCal scheduling links that log meetings to Salesforce or HubSpot
  • AI agents for spam checking and meeting prep, and 24/7 AI chat on Experiences

Watch out for

  • No free plan or self-serve trial; plans are sold after a demo
  • Annual billing only; the pricing FAQ says monthly billing is not available
  • The entry plan costs $15,000 a year, and ChiliCal on its own needs at least 200 seats

Questions

Is Calendly or Chili Piper cheaper?

They price different things, so neither is simply cheaper. Calendly's entry price, $10/seat/mo billed annually (Standard), is per user or seat; Chili Piper's, $1,250/mo billed annually (Routing & Scheduling), is for the whole plan. Price the number of people, channels or contacts you have on each.

Do Calendly and Chili Piper have free plans?

Calendly does; Chili Piper does not.

Every fact here comes from each vendor's own pages; the sources are listed on the Calendly and Chili Piper pages.