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Calendars · head to head

Outlook Calendar vs Timely

Outlook Calendar logo

Outlook Calendar

Calendars

Professional calendar management for Microsoft 365

From
Free
Rated
-
Full reviewWebsite
Timely logo

Timely

Scheduling

Smart scheduling software with AI-powered features

From
$11/month
Rated
-
Full reviewWebsite

The short version

  • Only Outlook Calendar has a free tier, so it costs nothing to try first.
  • Each has a real cost: Outlook Calendar offline support limited to only past 30 days of events, older events unavailable; Timely starter is capped at 20 projects and a maximum of 5 users, at $11 per user per month billed monthly or $9 billed yearly
  • They diverge on capability: Outlook Calendar covers Meeting scheduling, Timely covers AI-powered scheduling.
  • Prices and features above were last checked on 30 August 2026.

Where they differ

Only the attributes on which Outlook Calendar and Timely actually diverge.

Attributes where Outlook Calendar and Timely differ
AttributeOutlook CalendarTimely
Starting priceFree$11/month
Pricing modelUnknownsubscription
Free tierYesNo
PlatformsWeb, Windows, macOS, iOS, AndroidWeb, Ios, Android, Api
CategoryCalendarsScheduling
Founded19752015

Identical on both: 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 Timely

  • AI-powered scheduling
  • Online booking
  • Automated reminders
  • Staff management
  • Client management
  • Resource allocation
  • Analytics and reporting
  • Mobile app

Both cover

  • Slack

What people use each for

The jobs each tool is most often brought in to do.

Outlook Calendar

  • Schedulingnot Timely
  • Appointment bookingnot Timely
  • Time trackingnot Timely
  • Resource managementnot Timely
  • Team coordinationnot Timely

Timely

  • Team time tracking for professional servicesnot Outlook Calendar
  • Project billing and utilization reportingnot Outlook Calendar
  • Workforce capacity planningnot Outlook Calendar
  • Multi-team time management across currenciesnot 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

Timely

  • Starter is capped at 20 projects and a maximum of 5 users, at $11 per user per month billed monthly or $9 billed yearly
  • Premium is capped at a maximum of 50 users, at $20 per user per month billed monthly or $16 billed yearly
  • Unlimited users requires the Unlimited plan at $28 per user per month billed monthly or $22 billed yearly
  • Capacity management and reporting, overtime and undertime tracking, Azure user management and 50+ currencies are all on the Unlimited plan only
  • Team management, budgets and costs, and accounting and project management integrations are excluded from Starter
  • The Enterprise plan is contact sales only with no published price
  • Tasks is sold as a paid add-on rather than being included

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

Timely

$11/month
  • Starter$11/month
    • Up to 5 users
    • Up to 20 projects
    • Basic time tracking
  • Premium$20/month
    • Up to 50 users
    • Unlimited projects
    • All Starter features
  • Unlimited$28/month
    • Unlimited users
    • Unlimited projects
    • All Premium features
  • Enterprise$null/month
    • Custom pricing
    • All features

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.
Outlook Calendar review

Choose Timely if

  • You need ai-powered scheduling.
  • You work on Web, Ios, Android, Api.
  • You also want online booking.
Timely review

Questions people ask

Is Outlook Calendar or Timely better?
Neither clearly leads. Outlook Calendar starts at Free and Timely at $11/month, and user ratings are close enough to be indistinguishable. Choose on capability and platform support.
Which is cheaper, Outlook Calendar or Timely?
Outlook Calendar has a free tier; the other does not. Paid plans start at Free for Outlook Calendar and $11/month for Timely.
Does Outlook Calendar or Timely run on more platforms?
Outlook Calendar runs on Web, Windows, macOS, iOS, Android. Timely runs on Web, Ios, Android, Api.
Can I use Outlook Calendar for free?
Yes. Outlook Calendar has a free tier, so you can try it without paying. Timely starts at $11/month.
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 Timely is typically brought in for.
What can Outlook Calendar do that Timely cannot?
Outlook Calendar covers Meeting scheduling, Shared calendars, Room booking, Availability sharing. Timely covers AI-powered scheduling, Online booking, Automated reminders, Staff management. Both handle Slack.

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.

Source
Timely: Does Timely offer a free trial?

Yes, Timely provides 14 days of full feature access without requiring a credit card.

Source
Outlook 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.

Source
Timely: What annual discounts does Timely offer?

Annual billing discounts range from 20% to 22% off monthly prices. Starter saves 20%, Premium saves 21%, and Unlimited saves 22% when billed yearly.

Source
Outlook 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.

Source
Timely: Can I add team members to the Starter plan?

Starter plan supports a maximum of 5 users. For larger teams, Premium supports up to 50 users and Unlimited supports unlimited users.

Source
Outlook 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.

Source
Timely: What is the cost of Timely's Tasks feature add-on?

The Tasks feature starts at $5 per person per month and is available across all Timely plans.

Source
Outlook 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.

Source
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