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9 Best AI Scheduling Assistant Apps in 2024

Best AI Scheduling Assistant Tools in 2024

Have you ever considered how much time and mental effort it takes to stuff and prioritize all the tasks and meetings into your calendar?

study of 6,000 professionals revealed a surprising fact: on average, people spend almost 20% of their workweek playing calendar Tetris. That’s like dedicating one full 8-hour day each week to the puzzle of calendar planning! The struggle is real, especially when coordinating with international teams across multiple time zones.

Drawing from my 11+ years in the commercial aviation industry, I’ve faced firsthand the chaos of managing global projects and teams. Planning ahead and staying organized is crucial for maintaining productivity and reducing stress.

But, the game changed with the advent and vast applications of AI. The latest smart calendar apps offer intelligent scheduling suggestions and efficient calendar management.

After extensive research and hands-on experience, I’ve identified the top 9 AI scheduling assistants that truly harness artificial intelligence for scheduling suggestions and hassle-free calendar management.

Read on to learn how these new solutions can help you focus on your goals instead of calendar logistics.

What are The Best AI Scheduling Assistants?

Ever wonder which AI scheduling assistant is the best for your task management? What you should be looking for are smart tools that go beyond basic calendar functions, leveraging AI to automate planning and coordination.

I’m sharing my top picks for the best AI scheduling assistants to save you time, prevent double bookings, and take the tedium out of scheduling.

  • Motion: Best for AI-enhanced project management, meeting scheduling, and productivity boost.
  • Trevor: Best for time-blocking and effortless control over daily tasks and meetings.
  • Clara: Best for employing a human-like AI assistant for meticulous calendar management.
  • Kronologic: Best for utilizing AI scheduling in lead generation and conversion processes
  • Clockwise: Best for synchronizing and optimizing team calendars for improved time management.
  • Reclaim: Best for balancing work and habits in student and team schedules.
  • Calendly: Best for eliminating email back-and-forth and streamlining scheduling.
  • Sidekick AI: Best for flexible scheduling and smart meetings, the AI agent that converts customers effortlessly.
  • Schedule.cc: Best for seamless appointment generation and management.

Motion (Web, iOS and Android)



To me, Motion is the closest thing to having a real personal assistant – but one that works 24/7 without the hefty price tag or mood swings. Leveraging artificial intelligence, Motion takes care of your calendar planning, meeting scheduling, and project management with just a few clicks.

Essentially, Motion aims to automate the scheduling and coordination process as much as possible, freeing you and your team to focus on execution. It claims to save you a whole month’s worth of scheduling effort!

This intelligent calendar app uses AI to analyze your data – including scheduling behavior, preferences, and tasks – to create optimized plans tailored to you. It uses machine learning to learn and adapt to your working patterns, creating a schedule based on your optimal working time. Put simply, the more you use Motion, the better it gets in organizing your schedule.

It’s not just for individuals; it syncs with your entire team’s calendars and to-do lists, ensuring seamless coordination and timely completion of tasks!

Key Benefits

  • AI-driven automated planning. Perfect for those eager to (significantly!) cut down on planning and prioritize action. Motion merges your calendars, to-do lists, and meetings into one organized schedule, complete with time blocks. This approach boosts focus on current tasks and prevents overcommitment and the need for overtime, ensuring a balanced work-life.
  • Effortless Meeting Setup. Forget about back-and-forth email exchange or switching to another software to schedule a meeting. Just a few clicks to create and share a customized booking page and meeting link that reflects your availability and preferred meeting times.
  • Adapting Schedule Changes with Ease. Changes to any schedule are inevitable. But when this happens, Motion’s AI instantly reprioritizes tasks for you and your team in just 1 click. Its flexibility means you and your team can easily roll with whatever comes up without losing momentum.
  • Projects Under Control. You get customizable, easy-to-understand reports showing remaining time, task status, and the project’s overall trajectory and progress. Choose between List and Kanban views for real-time updates. Plus, end-of-project reports offer valuable insights into the team’s performance and areas for future improvements.
  • Integrations. Motion stands out as an all-in-one productivity platform, offering a comprehensive solution enhanced by its wide array of integrations. Sync with Google Calendar, Microsoft Outlook 365, or iCloud Calendar for holistic task and event management. Easily schedule and join Zoom, Microsoft Teams, or Google Meet meetings within Motion. Use its Gmail integration for quick meeting reminders and rescheduling. Plus, connect to thousands of apps via Zapier for unmatched versatility.



You can choose one of two Motion pricing plans:

  • Individual: $19/month (billed annually) or $34/month (billed monthly).
  • Team: $12/user/month (billed annually) or $20/user/month (billed monthly).

Trevor (Web)



Trevor AI is an assistant that helps manage your tasks and utilizes the concept of time blocks to help you organize your tasks and make your day more productive. Emphasizing simplicity and intuitive design, Trevor streamlines your scheduling experience, allowing you to maintain control while reaping the benefits of AI assistance.

The core idea behind the Trevor scheduling assistant is to help you achieve the coveted Deep Work state. This state of heightened concentration and flow is within reach, thanks to Trevor’s brilliant blend of to-do lists and the time-blocking technique. This dynamic duo helps you:

  • Visualize and prioritize tasks in one unified space
  • Allocate task duration, aka time blocks, to every task
  • Schedule tasks into your calendar using drag and drop, creating a solid base for smooth workflow

This approach lets you focus intensely on one task at a time, be in full control over your schedule, and master your to-dos and daily planning. I know it might seem simple, but simplicity is Trevor’s superpower. If you’re after an intuitive planner or dipping your toes into the world of AI calendar apps, Trevor is your guy.

Trevor evolves with you. Thanks to its AI scheduler app capability, Trevor adapts to your work style, auto-setting task durations and suggesting the best times to tackle them. These suggestions pop up in your timeline, ready for you to accept, tweak, ignore, or auto-schedule.

With Trevor, you enjoy the capabilities of AI technology without the complexity. User experience is straightforward, so it doesn’t feel overwhelming as with some more dense AI calendar tools. Trevor provides clarity on what to do and when with its clean interface across two well-designed views: your Task list and Calendar.

Key Benefits

  • Master Time-Blocking with Ease. Trevor intuitively guides you through time blocking with its effortless drag-and-drop system, ingraining this effective habit. Regular use will transform how you manage time daily.
  • Cultivating Deep Work. Trevor’s time blocking system aids focus and promotes deep work, minimizing distractions. It builds your concentration “muscle” for heightened productivity.
  • Explore Trevor for Free. The free plan lets you explore Trevor’s features at no cost. The paid version has a 30-day money-back guarantee for risk-free testing.
  • Outstanding task reminders. Trevor highlights overdue tasks, so you always remember to return to unfinished work. Daily email digests summarize achievements and uncompleted tasks, keeping you focused each morning.
  • Personalized AI Planning. AI-driven planning assistance provides personalized advice for task scheduling and execution. This includes predicting task duration for realistic schedules, recommending optimal time slots, and generating step-by-step plans to carry out tasks smoothly.
  • In-depth Performance-Based Insights. Trevor’s My Progress dashboard delivers actionable insights to optimize time use and sharpen productivity habits for continual performance gains.
  • Integrations. Trevor instantly syncs with Todoist and connects with Google Calendar, Outlook, and Office 365. Upcoming integrations include Google Tasks and Microsoft To Do, further enhancing its connectivity.


You can choose one of two Motion pricing plans:

  • Free Plan.
  • Pro Plan: $3.99 per month or $29.99 per year

Clara (Web, inbox)



Clara is a robust virtual assistant designed to streamline your meeting scheduling process. Using advanced natural language processing, Clara can automatically schedule, reschedule, and handle cancellations in real time through simple email exchanges. Once you cc Clara in your emails, she efficiently manages all meeting coordination tasks, eliminating endless email threads and freeing you to focus on meeting preparation.

Clara also offers 24/7 support, proposing suitable meeting times, sending out invitations, and delivering real-time event reminders. Her proficiency in understanding complex scheduling requirements is enhanced by the human-in-the-middle support provided by Clara Labs. This unique blend of AI and human intelligence ensures seamless integration into your workflow, making Clara versatile for managing professional communication.

Moreover, Clara’s premium plan allows customization of her name and email domain, adding a touch of personalization and mystery for your invitees. Clara AI is your virtual employee committed to optimizing your scheduling process while maintaining a human-like interaction experience.

Key Benefits

  • Automated scheduling: Clara can help you schedule meetings by CCing her on email chains. She will then reach out to your recipient to find a time that works for both of you.
  • Prompt response: Clara usually responds within a few minutes, with the median response time under 30 minutes.
  • Natural language: Clara is driven by AI, but it has a team of experienced Executive Assistants double-checking every mail that Clara drafts and categorizing conversations to teach Clara about etiquette and the nuance of conversation.
  • Meeting preferences: Clara can learn your meeting preferences and suggest times that work for you.
  • Reminders: Clara can send you reminders about upcoming meetings and tasks.
  • Reporting: Clara can provide reports on your meeting schedule and productivity.
  • Integrations: Clara integrates with other apps, such as Zoom, Google Meet, and Microsoft Teams.

Pricing (to be updated!)

Clara pricing

Clara is in the process of updating its pricing structure, with details expected to be released soon. The image above offers a snapshot of Clara’s pricing from the past year as a reference point for what was previously in place.

Kronologic (Web)



Kronologic stands out among AI calendar apps, tailor-made to boost conversion rates for sales teams by efficiently managing leads and optimizing their pipeline. A unique blend of automation and personalization, it utilizes AI capabilities to schedule and reschedule meetings automatically, minimizing the need for back-and-forth communication.

Kronologic’s natural language processing features effectively manage potential rescheduling requests, ensuring seamless calendar management. Its high-density scheduling feature enables mass scheduling, which is ideal for contacting many leads while avoiding unnecessary team chaos.

Kronologic is not just a tool; it’s a strategic partner that understands your objectives and refines the user experience to maximize returns. It simplifies the lead conversion process, automates task lists, and lets your team focus on closing deals. Powerful integrations and a dedicated AI-powered chatbot enhance Kronologic’s user experience, establishing it as a comprehensive solution in AI calendar apps.

Key Benefits

  • Lead generation: Kronologic can schedule invites for potential customers, send automatic messages, and track the performance of your lead generation campaigns.
  • Predictive lead scoring: Kronologic uses a predictive machine learning model to calculate the score for open leads. This helps salespeople know which leads to focus on and which are most likely to convert.
  • Calendar management: Kronologic can help you manage your calendar more effectively by automatically scheduling meetings, sending reminders, and tracking your time.
  • Task management: Manage your tasks more effectively by creating to-do lists, setting deadlines, and monitoring progress.
  • Communication: Improve communication with your team by sending messages, scheduling calls, and managing your email.
  • Reporting: Kronologic provides detailed reports on your lead generation, calendar management, and management tasks activities. This helps you to track your progress and identify areas for improvement.


Kronologic pricing

Kronologic offers various pricing plans depending on the size of your team.

Clockwise (Web)



Clockwise is an advanced AI-powered scheduling tool that entirely transforms the way you handle your calendar. With the trust and endorsement of over 200,000 Google Calendar users and organizations such as Twitter, Zoom, and Etsy under its belt, Clockwise refines your timetable to strike the perfect balance between productivity and personal life.

This AI calendar app leverages your work preferences to create the ideal day, blocking time for lunch, project catch-ups, thinking, and Focus Time to minimize distractions and boost productivity. Clockwise offers scheduling suggestions for efficient one-on-ones and team meetings while preserving focus time and reducing calendar conflicts.

It integrates with tools like Slack and Asana, updating your status based on your calendar and assigning tasks accordingly. Clockwise provides real-time analytics for team leads to monitor team bandwidth and ensure healthy work boundaries. The most customizable engine among AI calendar apps, Clockwise provides personalized scheduling capabilities that help create more time in your day.

Key Benefits

  • Intelligent scheduling: Clockwise AI can help you schedule events more effectively by considering your availability, the availability of the people you need to meet with, and your team’s overall calendar constraints.
  • Focus Time: Clockwise AI can help you protect your focus time by blocking out time on your calendar for uninterrupted work.
  • Meeting insights: Clockwise AI provides insights into your meeting habits, such as how often you attend meetings, how long they last, and who you meet with most often.
  • Integrations: Clockwise AI integrates with Slack, Zoom, and Asana productivity tools. It also connects with Google Calendar and offers convenient Chrome and Firefox extensions. Excitingly, they were beta testing Microsoft Outlook calendar compatibility as of November 2023, so a full launch could be just around the corner!


Clockwise pricing

A free plan covering basic functionalities is available; for more advanced features, team productivity tools, and enhanced security and support, premium plans commence at $6.75 per user per month.

Reclaim (Web)



Reclaim is a dynamic AI scheduling assistant that transforms teams’ management and prioritization of tasks. Harnessing advanced AI scheduling algorithms, Reclaim tailors personalized weekly schedules, creating an optimal balance between priority tasks, meetings, and personal habits. Reclaim integrates with your routine with a calendar-like interface, defending crucial work hours and automatically finding the most suitable time slots for meetings and important tasks.

One of its key features includes ‘Smart 1:1s’, which simplifies the scheduling of one-on-one meetings by automatically finding suitable timings and accommodating changes as required. With a simple dashboard, Reclaim gives you a comprehensive overview of upcoming tasks and meetings, saving you from the hassle of back-and-forth emails and manual rescheduling.

In addition, Reclaim prioritizes work-life balance by automatically scheduling breaks, limiting meeting hours, and protecting personal time. This AI-powered tool offers seamless integration with task management apps, effectively automating your scheduling process, enhancing productivity, and reclaiming up to 40% of your time. Although currently available only as a web app, Reclaim is also designed for a satisfactory mobile experience.

Key Benefits

  • Intelligent scheduling. Reclaim AI can help you schedule meetings more effectively by considering your availability, the availability of the people you need to meet with, and your team’s overall calendar constraints.
  • Buffer time. Reclaim AI introduces buffer time to safeguard your focus and prevent the rush between meetings and tasks. This thoughtful feature allows smoother transitions, ensuring you get the necessary breaks to stay sharp and productive throughout the day.
  • Task prioritization. Effortlessly prioritize your tasks using a combination of factors, such as due dates, estimated completion time, and priorities.
  • Habit tracking. Reclaim AI can help you track your habits by setting reminders and tracking your progress. This can help you build new habits and break bad habits.
  • Integrations. Reclaim AI integrates with many productivity tools like Todoist, Slack, Zoom, Google Tasks, Asana, Jira, ClickUp, Linear, and Raycast. Integrations with Trello and Monday are on the way.


Reclaim pricing

A free plan offers access to 2 calendars, three habits, and a limited set of integrations and features for enhanced functionality, including unlimited calendars, unlimited habits, expanded integrations, and more advanced features; paid plans commence at $8 per month.




Calendly is one of the leading AI calendar apps known for its power, ease of use, and versatility in scheduling solutions. Ideal for businesses and professionals alike, Calendly provides an accessible platform where users can establish their availability, enabling clients or team members to schedule appointments seamlessly. This process is simplified through a unique link that can be shared via email or embedded in a website.

Calendly goes beyond basic calendar availability with various features that support one-on-one, round-robin, and collective availability meetings. Its compatibility with various calendar platforms such as Google, Outlook, Office 365, and iCloud further enhances its usability. 

The app also offers customization options, time zone detection, buffers, and automatic SMS and email notifications. Integration with apps like Salesforce, Zapier, GoToMeeting, Slack, Intercom, and various platforms, including Google Meet and Zoom, makes Calendly a robust AI scheduling assistant, ensuring a streamlined user experience.

Key Benefits

  • Intelligent scheduling: Calendly AI can help you schedule meetings more effectively by considering your availability, the availability of the people you need to meet with, and your team’s overall calendar constraints.
  • Automated booking: Calendly AI can automatically book meetings based on your preferences and availability.
  • Meeting insights: Calendly AI can provide insights into your meeting habits, such as how often you attend meetings, how long your meetings are, and who you meet with most often.
  • Integrations: Calendly boasts a broad range of integrations, connecting effortlessly with tools like Slack, Microsoft Teams, Google Meet, Zoom, Webex, Gong, and Notion, among others. It seamlessly links Google Calendar, Outlook/Office 365, and iCloud calendars.


Calendly pricing

Calendly provides a free plan for users. However, if you require advanced functionalities such as integrating multiple calendars or creating group events, consider upgrading to their reasonably priced paid plan.

Calendly: From Free to Custom – Find Your Fit!

Sidekick AI

Sidekick AI


Sidekick AI is one of the best AI scheduling assistants to streamline your meeting and event organization. Leveraging language processing and AI algorithms, it offers multiple scheduling options, allowing you to automate your appointment bookings efficiently and quickly. The AI scheduler app provides three main scheduling features: Sidekick Scheduling, Forward to Schedule, and Scheduling Pages.

The Sidekick Scheduling feature finds the best meeting time and sends requests to both Sidekick and non-Sidekick users. Forward to Schedule simplifies meeting arrangements by letting you forward an email to Sidekick for it to handle the details, eliminating the need for tedious back-and-forths. Scheduling Pages enables you to create custom shareable web pages for individual meetings.

The platform integrates smoothly with widely-used tools like Microsoft Teams, Google Calendars, and Zoom, synchronizing seamlessly with your existing workflow. Sidekick AI’s advanced team scheduling capabilities also make organizing group meetings hassle-free.

For a more personal touch, the scheduling software allows customization of your scheduling pages, with options to include a logo, description, and unique preferences. Moreover, it offers automated meeting reminders, ensuring no appointment is missed. Whether you need to schedule discovery calls, demos, or kickoff calls, Sidekick AI optimizes the process, making scheduling painless and efficient.

Key Benefits

  • Schedule meetings: Use Sidekick to schedule meetings by finding a time that works for everyone involved. It can also help you to send out meeting invitations and track RSVPs.
  • Find meeting times: Sidekick can help you find meeting times by taking into account your availability, the availability of the people you need to meet with, and your team’s overall calendar constraints.
  • Time blocking: Sidekick lets you block time on your calendar for focus work or other commitments. This can help you to avoid feeling rushed and to give yourself time to transition between tasks.
  • Automate scheduling: Sidekick can automate scheduling by automatically scheduling meetings for you based on your preferences and availability.
  • Send meeting reminders: Sidekick can send meeting reminders to you and the people you are meeting with. This can help you to remember meetings and to make sure that everyone is on the same page.


Sidekick pricing

Sidekick offers two pricing plans:

  • Hero PlanFree 
  • Superhero Plan$5/month

Schedule CC

Schedule CC


Schedule CC is one of the best AI scheduling assistants that revolutionizes how businesses and individuals manage their appointments and events. This AI tool offers a comprehensive solution to streamline the scheduling process, minimizing the need for back-and-forth emails while maximizing appointment generation from your website and emails.

The standout features of Schedule.CC include its built-in video conferencing through 500Conference, enabling seamless, high-definition audio and video interactions. Its automated scheduling feature improves efficiency and enhances customer satisfaction by reducing no-shows through proactive appointment reminders.

Further, Schedule.CC facilitates easy and professional payment collection before appointments, ensuring a smooth transactional experience. Its flexible online scheduling capabilities cater to one-on-one sessions and group events, with adjustable event duration and invitee limits.

The software integrates seamlessly with various platforms, including CRM systems, Gmail, Stripe payments, and WordPress. From online schedulers, embeds, and AI chatbot integration to Gmail extension for sharing schedule links, Schedule.CC truly encompasses a comprehensive automated scheduling solution.

Key Benefits

  • Online booking: Schedule.CC allows clients to book appointments online, 24/7. This can help you to save time and improve your customer service.
  • Availability calendar: Schedule.CC displays your availability calendar so clients can see when you can meet. This can help you avoid double bookings and ensure you are always available to meet with clients.
  • Customization: Schedule.CC is highly customizable so that you can tailor it to your specific needs. You can change the software’s colors, fonts, and layout to match your branding.
  • Reports: Schedule.CC’s reporting feature efficiently tracks your appointments and meetings by day, date, and category. This functionality provides a clear overview of your scheduling trends, including self-booked events and those booked by clients.
  • Integrations: Schedule.CC integrates with various other software, such as Google Calendar, Slack, and Zapier. This can help you to streamline your workflow and to keep all of your appointments in one place.


Schedule CC pricing

You can get all 50 Schedule.CC’s apps with monthly or yearly cloud plans for just $14.99 per month.

Elevate Your Scheduling Experience. Try Schedule.CC!

What is an AI Scheduling Assistant?

AI Scheduling Assistants are advanced software solutions that use artificial intelligence technology to automate and streamline the process of scheduling appointments, meetings, and events.

These AI calendar apps analyze user calendars and suggest optimal time slots for scheduling, reducing conflicts and saving considerable time. They interpret and respond to scheduling requests through natural language processing, eliminating the need for tedious back-and-forth communication. Additionally, these AI tools provide reminders, handle rescheduling and manage cancellations, helping to prevent missed appointments.

Their ability to integrate with existing productivity tools, such as email, calendar apps, CRM systems, video conferencing tools, and payment gateways, makes them versatile and convenient. Over time, they learn from the user’s patterns and behaviors, providing increasingly personalized and efficient scheduling solutions. By significantly improving efficiency, productivity, and time management, AI Scheduling Assistants have become an essential tool for both businesses and busy individuals.


Reflecting on the journey from AI as a sci-fi concept to its tangible impact on our lives today, I couldn’t be more excited. As someone who has personally struggled with messy calendars, I empathize with those yearning for a more streamlined approach to time management.

Today’s productivity landscape is blessed with various AI scheduling assistants, each with unique strengths and capabilities. From Motion’s focus on project management and Clara’s human-like email scheduling to Kronologic’s sales-oriented organization, there is an AI tool for everyone’s needs. The stories of Sidekick AI saving time with its smart meetings or how Kronologic is becoming a powerful ally for sales teams are a few examples of how AI continually reshapes our lives.

By sharing these insights with you, I hope to help you navigate the ubiquitous world of AI scheduling assistants and find the perfect tool for your unique needs. Happy scheduling!

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