Calendar & Time Management · head to head
Outlook Calendar vs Calendly
Outlook Calendar
Calendar & Time Management
Professional calendar management for Microsoft 365
- From
- Free
- Rated
- -
Calendly
All industries
Scheduling automation platform for eliminating back-and-forth
- From
- Free
- Rated
- -
The short version
- Each has a real cost: Outlook Calendar offline support limited to only past 30 days of events, older events unavailable; Calendly the free plan allows one event type and one calendar connection, so it cannot handle different meeting formats
- They diverge on capability: Outlook Calendar covers Meeting scheduling, Calendly covers Calendar sync.
Where they differ
Only the attributes on which Outlook Calendar and Calendly actually diverge.
| Attribute | Outlook Calendar | Calendly |
|---|---|---|
| Platforms | Web, Windows, macOS, iOS, Android | Web, iOS, Android |
| Category | Calendar & Time Management | All industries |
| Founded | 1975 | 2013 |
Identical on both: starting price (Free), pricing model (Unknown), free tier (Yes), user rating (Not yet rated).
What each one covers
Drawn from each product's published feature list. An absence here means we hold no record of it - not that the product lacks it.
Only in Outlook Calendar
- Meeting scheduling
- Shared calendars
- Room booking
- Availability sharing
- Recurring events
- Microsoft Teams
- OneDrive
- SharePoint
Only in Calendly
- Calendar sync
- Automated scheduling
- Custom availability
- Time zone detection
- Reminder emails
- Buffer time
- Meeting polls
- Embed on website
Both cover
- Slack
- Zoom
What people use each for
The jobs each tool is most often brought in to do.
Outlook Calendar
- Schedulingnot Calendly
- Appointment bookingnot Calendly
- Time trackingnot Calendly
- Resource managementnot Calendly
- Team coordinationnot Calendly
Calendly
- Sales meetingsnot Outlook Calendar
- Interview schedulingnot Outlook Calendar
- Customer callsnot Outlook Calendar
- Office hoursnot Outlook Calendar
- Webinar registrationnot Outlook Calendar
Where each one falls short
Documented limitations, not opinions. Every one is a constraint you would hit in normal use.
Outlook Calendar
- Offline support limited to only past 30 days of events, older events unavailable
- Shared calendars and group calendars not available offline
- Cached Exchange Mode issues can limit available offline data
- Occasional sync conflicts when coming back online
Calendly
- The free plan allows one event type and one calendar connection, so it cannot handle different meeting formats
- Automated reminders and multiple calendars need Standard at $10 per seat per month
- Round-robin routing, lead qualification and Salesforce integration require Teams at $16 per seat per month
- SAML single sign-on, audit logs and domain control are Enterprise only, starting at $15,000 a year
- Advertised prices are the annual rates
Pricing, plan by plan
Outlook Calendar
Free- FreeFree
- Outlook.com email and calendar
- 50MB attachment limit
- 1GB cloud storage
- Microsoft 365 Basic$19.99/year
- Outlook with limited features
- Cloud storage
- Microsoft 365 Personal$99.99/year
- Premium Outlook
- Ad-free email
- 100GB mailbox storage
- Microsoft 365 Business Basic$6/month
- Business-class email
- 1TB cloud storage
- Microsoft Teams
Calendly
Free- FreeFree
- 1 event type
- 1 calendar connection
- Basic confirmation email
- Standard$10/month
- Unlimited event types
- Multiple calendars (up to 6)
- Integrations with HubSpot, Mailchimp, Stripe, PayPal
- Teams$16/month
- All Standard features
- Salesforce integration
- Round-robin meetings
- Enterprise$15000/year
- All Teams features
- Salesforce routing lookup
- Microsoft Dynamics 365
Which should you pick?
Choose Outlook Calendar if
- You need meeting scheduling.
- You want to start without paying.
- You work on Web, Windows, macOS, iOS, Android.
- You also want shared calendars.
Choose Calendly if
- You need calendar sync.
- You want to start without paying.
- You work on Web, iOS, Android.
- You also want automated scheduling.
Questions people ask
- Is Outlook Calendar or Calendly better?
- Neither clearly leads. Outlook Calendar starts at Free and Calendly at Free, and user ratings are close enough to be indistinguishable. Choose on capability and platform support.
- Which is cheaper, Outlook Calendar or Calendly?
- Outlook Calendar starts at Free and Calendly at Free.
- Does Outlook Calendar or Calendly run on more platforms?
- Outlook Calendar runs on Web, Windows, macOS, iOS, Android. Calendly runs on Web, iOS, Android.
- Can I use Outlook Calendar for free?
- Both have a free tier, so you can try either at no cost before committing.
- What is Outlook Calendar best used for?
- Outlook Calendar is most often used for scheduling, appointment booking, time tracking, resource management. Of those, scheduling and appointment booking are not what Calendly is typically brought in for.
- What can Outlook Calendar do that Calendly cannot?
- Outlook Calendar covers Meeting scheduling, Shared calendars, Room booking, Availability sharing. Calendly covers Calendar sync, Automated scheduling, Custom availability, Time zone detection. Both handle Slack, Zoom.
Answered from the vendors’ own pages
Outlook Calendar: Is Outlook Calendar free?
Outlook.com with calendar is free via a Microsoft account. Outlook Calendar also comes with Microsoft 365 Personal ($99.99/year), Family ($129.99/year), or Business plans starting at $6/user/month.
SourceCalendly: Does the free tier include automatic reminders?
No. The free plan only includes a basic confirmation email when someone books. Automated reminder workflows, SMS reminders, and follow-up sequences require the Standard plan ($10/month or higher).
SourceOutlook Calendar: Does Outlook Calendar work offline?
Outlook Calendar has limited offline support. New Outlook caches only the past 30 days of calendar items. Shared calendars and group calendars are not supported offline. Changes sync when you reconnect.
SourceCalendly: Can I offer multiple meeting types on the free plan?
Only one event type can be active at a time. You can create multiple event types, but only one booking link works simultaneously. Switching between different meeting lengths requires manually activating another event type.
SourceOutlook Calendar: What platforms does Outlook Calendar support?
Outlook Calendar is available on Windows (desktop and web), macOS (desktop and web), iOS, and Android. Real-time synchronization works across all devices.
SourceCalendly: Does Calendly work with Apple Calendar and iCloud?
No longer for new users. As of August 20, 2024, new users cannot connect iCloud or Apple Calendar. Existing connections continue to work, but Calendly ended support for new Apple Calendar integrations citing Apple's security changes.
SourceOutlook Calendar: Does Outlook Calendar integrate with Slack?
Yes. Outlook Calendar integrates with Slack to sync your status and receive meeting notifications. You can RSVP to invites directly in Slack and join Microsoft Teams meetings from Slack reminders.
SourceCalendly: What platforms can I use Calendly on?
Calendly is available on Web, iOS, and Android. Browser extensions are available for Safari. There are no dedicated Windows or Mac desktop applications.
SourceOutlook Calendar: Can you share calendars and set delegate permissions?
Yes. Outlook Calendar supports calendar sharing with delegate permissions, color categories for organization, and the Scheduling Assistant to view attendee availability for meeting times.
SourceCalendly: What does the Standard plan ($10/month) add over free?
Unlimited event types, multiple calendar connections (up to 6), integrations with HubSpot, Mailchimp, Salesforce, Stripe, PayPal, Zapier, and webhooks, plus automated reminders and email sequences.
Source