Calendly vs. Chili Piper: Which scheduling app is better?

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Struggling with a backlog and chaotic schedules? Find out how to streamline your appointment booking processes in this Calendly vs. Chili Piper comparison.

Free - $20/mo (per seat)
$22.5/mo - $45/mo
Everyone from small businesses to Fortune 100 companies looking for a tool to make scheduling (and remembering) meetings easier.
Large marketing or revenue teams
Free - $20/mo (per seat)
Everyone from small businesses to Fortune 100 companies looking for a tool to make scheduling (and remembering) meetings easier.
$22.5/mo - $45/mo
Large marketing or revenue teams

Most scheduling apps today claim they can streamline appointment booking.

However, they lack details on how they can help users streamline scheduling to improve productivity.

So, we researched two schedulers that have recently gained popularity: Calendly and Chili Piper.

Let’s look at how they compare and see what makes each unique in this Calendly vs. Chili Piper comparison.

Calendly vs Chili Piper: At a Glance

CriteriaCalendlyChili PiperWinner
SMB Guide’s Rating9/109/10Calendly
Appointment Workflow AutomationChili Piper
Customization OptionsCalendly
Calendar Management FeaturesCalendly
Automated Reminders and NotificationsCalendly
Client Management & CommunicationTie
Automatic RulesTie
In-Meeting ToolsChili Piper
Meeting TemplatesTie
UX and UIHigh user-friendlinessFocuses on functionalityCalendly
Integrations & API CapabilitiesCalendly
Supported PlatformsCalendly
Customer SupportLive chat, automated chat box, email support ticketsLive chat and emailTie
PricingFree – $20/mo (per seat)$22.5/mo – $45/moCalendly

Calendly: Key Features, Pros, Cons, & Pricing

calendly homepage

Calendly is an all-rounded scheduler, unlike Chili Piper, that allows for the scheduling of appointments of various types.

The software simplifies scheduling through the automation of routing and reminders. You can create various event types and forms with targeted questions for the leads.

Then, from there, use logic-based automation to guide the clients to book the right appointment through a URL.

Pros & Cons


Free forever plan

iOS & Android apps

100+ integrations

Easy to build workflows


Too many features

Expensive for larger teams


Calendly pricing model is straightforward with four packages. The plans rise with tiers, with the entry plan free.

The paid plans get a 2-week trial period, and choosing the annual subscription allows for a 20% discount.

Here are the plans:

  • Free: $0
  • Standard: $12 per seat
  • Teams: $20 per seat
  • Enterprise: Custom

Chili Piper: Key Features, Pros, Cons, & Pricing

Chili Piper homepage

Chili Piper is a scheduler and routing software focusing on sales and marketing teams with a leaky funnel.

The software integrates with most CRMs, allowing for custom workflow and routing rules. In turn, they enable real-time scheduling and confirmation automation of appointments.

Pros & Cons


Easy-to-use interface

60+ integrations

Instant lead qualifying

Schedule meetings with ease


No free plan

Rescheduling meeting is challenging


Chili Piper’s pricing model is also straightforward, offering four plans. Unlike Calendly, Chili Piper lacks a free plan, but you can request a demo to test the inner workings of the software.

The plans rise with tiers, and subscribing to the annual plan offers a 33% discount. Here are the plans:

  • Instant Booker: $22.5 per user
  • Handoff: $37.5 per user
  • Form Concierge: $45 per user (Plus platform fee $225 – $1500)
  • Distro: $45 per user

Appointment Workflow Automation

Calendly and Chili Piper offer common features that ease appointment booking and improve convenience.

They include integration with several calendars like Outlook, Google and more. The softwares also allows for creating custom rules, appointment types and booking pages.

Sending follow-up messages is also available, where you can send emails and SMS with custom content.

Embedding booking links on email and team schedules are also available on both.

calendly appointment scheduling

However, unlike Chili Piper, Calendly has more event types, including a round-robin that helps distribute appointments evenly among staff, depending on availability.

Not only that, admins can create and manage events like, setting payment collection, max number of attendees, and more.

Calendly also allows recurring appointments with durations of 2 weeks or monthly to maintain client relationships.

Chili Piper instant booker

On the other hand, Chili Piper supports instant appointment booking via email, online forms, and more.

Admins can also route and schedule appointments with customers in real-time. Unlike Calendly, Chili Piper allows live calling once a lead books an appointment.

An admin can transcribe or record the live call for better insights. Chili Piper also allows you to incentivize appointment booking, where you can offer discounts or a reward to leads.

In fact, the software integrates with the Sendoso gifting platform for instant incentive delivery.

✅ Winner: Chili Piper

Customization Options

Calendly and Chili Piper both allow the creation and management of various appointment types, including group events and one-on-one.

Admins can also set appointment durations, depending on their preferences. However, unlike Chilli Piper, Calendly allows you to create unlimited events, each with a custom rule or setting.

The software also supports collective, group and round-robin scheduling, enabling even appointment distribution.

calendly events

Now, customizing the scheduling page is something Calendly excels at, unlike Chili Piper. An admin can tweak the logo or content and embed a link to their custom domain.

Not only that, but you also have access to a white-label option for removing Calendly branding on your emails or scheduling page.

Chili Piper has limitations with the customization options, especially for durations and meeting types.

One thing to note is that you can create internal, inbound, or outbound appointment types. 

However, customizing an event message, name, or location is impossible. Not only that, you have to use pre-defined durations for every appointment type like 20, 45 or 1 hour times.

Even though Chili Piper has round-robin, other scheduling options like group or collective aren’t available.

Customizing a scheduling page on Chili Piper also has limitations. Admins cannot use a custom domain or remove the Chili Piper branding from their emails or scheduling page.

However, you can tweak the content or logo of your brand.

✅ Winner: Calendly

Calendar Management Features

Calendly allows admins to create team pages showcasing staff availability, enabling leads to pick one they prefer.

You can also manage or add resources like meeting tools and assign them to specific events.

calendly calendar management

Now, Calendly syncs with most calendars, including Google and Outlook, allowing admins to set time zones.

The software automatically detects the time zone and converts the time to a specific region.

Then, from there, you can display the time zones on scheduling pages, allowing leads to choose the convenient slot time.

Chili Piper check-in calendar

Unlike Chili Piper, Calendly allows you to set custom rescheduling and cancellation rules.

You can set a cancellation fee, limit reschedules and more. The software also sends notifications automatically whenever a client reschedules or cancels an appointment.

Chili Piper cannot match Calendly management features, especially for multiple team members and resources.

However, you can create staff queues and assign clients to the team members, depending on expertise or availability.

Now, Chili Piper allows setting time zones, and the software converts it automatically depending on the client’s location.

However, the feature is basic, unlike Calendly, where admins cannot display several time zones on the scheduling page.

Not only that, Chili Piper only integrates with Google and Outlook Calendar. Rescheduling and cancellation on Chili Piper come with some limitations.

You cannot turn cancellation or scheduling on or off. Not only that,  the software also doesn’t send email alerts on cancellation or rescheduling of an appointment.

The only option admins get is setting custom rules on cancellation and rescheduling.

✅ Winner: Calendly

Automated Reminders and Notifications

Calendly supports sending automated reminders through SMS or email for client appointment booking.

The platform gives you the flexibility of sending as many alerts as possible and customizing the content of the message.

Calendly also allows you to send booking links through email to prompt customers to confirm attendance.

calendly automated reminders

One thing to note is that Calendly integrates with more calendars and CRMs than Chili Piper.

The software also provides automation templates for tasks like sending follow-up emails, updating records and more.

chili piper automated reminders

Chili Piper also automates sending reminders and delivering them by SMS or email.

However, there are some limitations. For example, users can only send a single reminder per appointment, and it limits message tweaking.

Not only that, the software doesn’t support SMS messages outside the US. Unlike Calendly, Chili Piper also lacks automation templates.

It requires admins to use Zapier to add any custom automation template.

✅ Winner: Calendly

Client Management and Communication

Calendly has a built-in email and SMS reminder feature that you can use to send alerts for any event.

You can also choose the notifications to receive, like cancellations, rescheduling, new bookings and more.

calendly text reminders

The admins can also pick the frequency of the alerts and even modify the message content with a variable like location, event name or date.

The software also connects to Slack and Microsoft to send in-app messages. Not only that, you can integrate Zapier, which can help integrate a medium of choice for sending reminders.

Chili Piper Hubspot automated reminders

Unlike Calendly, Chili Piper lacks a built-in reminder and relies on CRM integration like HubSpot to send messages.

However, admins can choose notification types they can receive, like new booking, reschedule, cancelation and more.

While you do have the ability to adjust reminder message content, it doesn’t offer the same level of comprehensive control and freedom as seen on Calendly.

✅ Winner: Tie

Automatic Rules

Calendly offers the auto-cancelation feature in the premium plans. It gives you the flexibility to enable it for any event.

Unlike Chili Piper, Calendly supports longer time frames for setting a confirmation due date between 1 and 7 days. 

Another thing to note is that the time zone adjustment feature is standard in all Calendly plans.

Plus, the working hours are flexible, and admins can set them to show availability. Chili Piper also offers the auto-cancelation feature in its 2 premium plans (Concierge & Enterprise).

You can enable it for any appointment type and set confirmation due dates. However, the time frames are shorter than Calendly, ranging from 1 to 24 hours. 

One thing to note is that the time zone adjustment feature is standard in all Chili Piper plans.

In addition, the working hours are flexible, and admins can set them to show their availability.

✅ Winner: Tie

In-Meeting Rules

Admins will not find a built-in meeting minutes or note-taking feature on Calendly. However, the software integrates with tools like Evernote that you can use to sync calendars and meeting notes. 

The software also has a custom question feature that you can use to ask leads for relevant data before the appointment.

Calendly doesn’t have a built-in collaboration feature, yet it does offer integration options with platforms such as Zoom for conducting video meetings.

Chili Piper lacks a built-in meeting minutes feature, but it offers a note-taking accessible in all plans.

The feature allows you to jot notes during the meeting or after and sync the data with the native CRM. 

Now, for meeting minutes, admins must integrate platforms like Gong or Zoom to help record or transcribe the meeting for later analysis.

Not only that, Chili Piper has a custom field feature that you can use for collecting data from leads before or after meetings.

✅ Winner: Chili Piper

Meeting Templates

Calendly and Chili Piper offer several meeting template options you can use for appointment types.

The templates on both softwares share similarities, but the design and focus are the major differences.

Calendly meeting templates

Calendly template design is simple and suits a wide variety of use cases. The templates also allow for customization, allowing admins to add buffers.

Not only that, you can duplicate or edit the existing ones to create new ones that meet your needs.

Chili Piper meeting templates

On the other hand, Chili Piper templates are complex and niched, catering to marketing and sales teams.

You can also customize them to your liking by adding custom fields. Similar to Calendly, you can duplicate or edit the existing ones to create new ones that meet your needs.

✅ Winner: Tie

User Experience and User Interface

Calendly provides a modern interface that’s easy to navigate. The dashboard is the central hub, and accessing any feature is one click away.

Admins also get the option of tweaking the platform. You can add or delete widgets, colors, or fonts that speak to your brand.

Not only that, the experience on the platform is also satisfying.

calendly dashboard

Chili Piper also has a modern interface, but it’s dashboard is challenging to navigate and full of clutter.

Chili Piper dashboard

The design of the software focuses on functionality, offering features that cater to sales and marketing.

Onboarding is also seamless, where the platform has tutorials with clear instructions and helpful customer support.

✅ Winner: Calendly

Integrations and API Capabilities

Calendly integrates with various systems, including HR tools like BambooHR and payroll platforms.

calendly integrations

The integrations help simplify appointment booking and payroll management without leaving the platform’s dashboard.

Admins looking to add a custom application or retrieve data from the database will find Restful APIs and webhooks.

Chili Piper integrates with HR systems like Workable but the stack is not as extensive as Calendly.

chili piper integrations

The software also allows for the customization of workflows based on need. Not only that, but Chili Piper also allows admins to add custom applications or retrieve data through Restful APIs and webhooks.

✅ Winner: Calendly

Supported Platforms

Calendly is a web-based platform accessible through a browser on platforms like Windows, macOS and Linux.

The software also offers a mobile app compatible with Android and iOS, allowing admins to access the workflows on the go.

The good thing is the app syncs well with the web version seamlessly. Chili Piper is also a web-based platform accessible through a browser on platforms like Windows, macOS and Linux.

Unlike Calendly, Chili Piper lacks a mobile application, and admins must use the web version to run their workflows.

✅ Winner: Calendly

Customer Support

Calendly offers 2 channels for reaching customer support: live chat and email. The response times on the live chat are instant, while email can take up to 6 hours.

calendly customer support

The platform also has an extensive customer education resource, including a blog and help center.

The content of the articles is in-depth, covering topics like productivity, recruitment and more.

Chili Piper also offers two channels for contacting customer support: email and live chat.

chili piper support

The email response times take up to 24 hours, while the live chat is instant. The platform also has a resource center, but not as extensive as Calendly’s.

However, it has guides and an FAQ section covering common queries.

✅ Winner: Tie


The pricing models of Calendly and Chili Piper are similar, but have some discreet distinctions.

Calendly offers tiered plans, with the entry package being free. The paid plans start at $12 per seat; the topmost package is custom.

Unlike Chili Piper, Calendly offers a 2-week trial period for software testing. Chili Piper also offers tiered plans but lacks a free plan.

The entry plan starts at $22.5 per user, and the topmost package costs $45 per user. One thing to note is that Chili Piper doesn’t offer a free trial but has a demo.

✅ Winner: Calendly


Calendly packages are scalable, providing more advanced features as you rise through the tiers.

The plans also suit different teams, from budget-conscious to large enterprises looking for custom packages.

Chili Piper also offers scalable plans that rise with tiers. The packages also fit different types of users, but mainly medium to large teams.

The software also offers standalone features that you can purchase at a custom price.

✅ Winner: Tie

Standout Features of Calendly

Calendly is a versatile platform, making it one of the best scheduler currently in the market.

Here are 2 features that make it stand out.

Customization options

Calendly supports the customization of the scheduling page, allowing admins to add images and colors that match the brand voice.

The software also allows the creation of custom quizzes and follow-up emails targeting the clients.

Admins can also set event types like round-robin, group or one-on-one.

Dynamic pricing

Calendly pricing is versatile, offering a free plan that suits solopreneurs on a budget looking to create an event type.

The other paid plans have reasonable pricing with a 2-week trial period.

Standout Features of Chili Piper

Besides being a scheduler built for sales and marketing teams, Chili Piper provides unique features that make it one of the best.

Here are 2 features that make it stand out.


It is a feature that enables admins to create a custom booking experience for their clientele.

The feature allows customizing the booking page and using dynamic rules that match leads to the ideal account manager.

Instant booker

It is a feature that allows admins to connect online forms, allowing leads to schedule appointments seamlessly.

The platform also offers appointment reminders that help to lower no-shows.

Calendly vs. Chili Piper: SMB Guide’s Verdict

Our Calendly vs. Chili Piper comparison shows that both software are decent schedulers.

The features they offer share similarities, like automated reminders and automatic rules.

However, their functionalities differ, with Calendly offering more advanced features that fit a wide range of businesses.

It is the reason Calendly is the winner, and here is why;

Calendly offers a free plan that appeals to budget-conscious teams. The pricing plans are scalable, and the cost is reasonable.

The software also offers extensive customization options, allowing admins to set event types like round-robin, group, one-on-one and more.

These and many more features are the reason Calendly wins. Chili Piper is a decent alternative, providing an instant booker and a unique Concierge feature.

However, the lack of a free plan and customization limitations make it lose to Calendly.

Choose Calendly If:

You need a versatile and affordable schedular that can streamline your appointment scheduling.

Choose Chili Piper If:

You need a scheduler for your revenue team to streamline the appointment pipelines.


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Jessica Pereira helps SaaS and digital marketing brands build long-lasting customer relationships with meaningful content. Her favorite topics include career development, productivity, and email marketing.