Uncommon Comforts Plain comparisons of the tools you keep your people and your work in

ChatGPT vs Microsoft Copilot in 2026

Compare ChatGPT, Microsoft Copilot and Connections Boardroom: what each does, pricing, getting started, and how to choose.

By Uncommon Comforts ยท

Uncommon Comforts is published by the team behind Connections, whose products are compared here alongside other tools.

ChatGPT has a free version available to everyone [1]. Microsoft Copilot has a free tier that requires a signed-in Microsoft account [2]. Connections Boardroom has several AI advisers answer in turn to what you say, and they can argue with each other [3]. It is for paying members only [3].

OptionFree optionPaid plans
ChatGPTA free version is available to everyone, with limited image creation, file uploads and deep research [1] [1] [1] [1]Go, Plus, Business and Enterprise are paid plans, priced per user per month; the amounts are not published here [1]
Microsoft CopilotA free tier is available with a Microsoft account [2]Microsoft 365 subscriptions include the Copilot app and premium features; their price is not published here [2]
Connections BoardroomConnections Free costs $0, and the Boardroom is for paying members only [3] [3]Connections Pro, the first paid plan, is $39.99 a month [3]; Connections Business is $99.99 a month [3]

The short answer

ChatGPT's page describes its intelligence for everyday tasks [1]. Microsoft Copilot helps you research, create and get answers, across work and personal life [2] [2]. Some capabilities are subject to usage limits, and more are available on paid plans [2]. Connections Boardroom works differently: you say one thing, and several advisers answer one after another, each from their own brief, and they can argue with each other [3].

Which one meets your needs depends on the job. ChatGPT's page describes its intelligence for everyday tasks [1]. Microsoft Copilot's free tier requires a signed-in Microsoft account [2]. If you want several AI advisers that respond to a prompt and argue with each other, and then get minutes and a plan written from the meeting, Connections Boardroom is described for that [3] [3].

What ChatGPT and Microsoft Copilot are built for

ChatGPT's own page says its free version is available to everyone [1]. ChatGPT Free includes everyday text chats [1], and it has limited image creation [1], limited file uploads [1] and limited deep research [1]. The page says ChatGPT works on the web, iOS and Android for the plans it lists [1]. It also says all data is encrypted in transit using TLS 1.2 [1].

Microsoft Copilot is free with a signed-in Microsoft account, and a free tier is available with a Microsoft account [2], and it is available on the web, desktop and mobile [2]. Its page says it helps you research, create and get answers, with some capabilities subject to usage limits and more available through paid plans [2]. Work and personal conversations stay separate, with chat history, files and organizational protections tied to the right account [2]. Copilot responds only when you choose to use it, and your existing privacy and security settings still apply [2]. Word, Excel and PowerPoint can also be used for free on the web [2].

What Connections Boardroom is built for

Connections Boardroom is made by the team that publishes this site, Uncommon Comforts. It is a standalone web app where you hold a meeting with a board of AI advisers [3]. You pick a scene, seat a few advisers and say the first thing on your mind [3]. Every workspace comes with five ready-made advisers and a starter boardroom scene [3]. You can also create your own board members by giving each one a photo, a written description and a voice [3]. Creating a board member costs one credit [3].

Any adviser can take any seat at the table, and swapping one in the middle of a meeting is a click [3]. An adviser with nothing to add replies with a pass instead of padding out the meeting [3]. The advisers can also ask you numbered questions about your plan, each with a suggested answer, and any question you skip takes that suggestion [3]. When the meeting is over, the minutes and the plan are written from it, and any number nobody stated in the meeting is marked so you can see it [3] [3]. You can drop in a PDF, a Word document or a screenshot, and the advisers read it [3]. You can dictate using your browser's speech recognition, and each reply is spoken aloud [3]. Every meeting is saved as a transcript you can leave and come back to later [3]. You can also change the background, table and chairs of the room your board meets in [3]. A member can have a meeting thought through by a model running on their own computer [3].

Pricing and fees

ChatGPT's page lists Go, Plus, Business and Enterprise as paid plans; their prices are not published here [1].

Microsoft 365 subscriptions include the Copilot app and additional premium features [2]. This page does not publish a price for that subscription or for Copilot's paid plans, so check Microsoft's current pricing [2].

Connections Free costs $0, and going over a limit stops the feature rather than billing you [3]. Connections Pro, the first paid plan, is $39.99 a month and adds premium features across every Connections product [3]. Connections Business is $99.99 a month, with higher limits across every Connections product [3]. The Boardroom is for paying members only, so a free Connections member has to upgrade to use it [3]. Meetings use up the member's Connections AI usage [3]. Creating a board member costs one credit [3].

Getting started

ChatGPT's free version is available to everyone [1], and its page lists web, iOS and Android access for the plans it names [1]. The page does not describe the sign-up steps, so look at the first screens before you commit.

Microsoft Copilot is free with a signed-in Microsoft account [2]. For the Copilot app, the minimum version on an iPhone is iOS 26 or later [2], and on an Android phone it is Android 13 or later [2]. If you already use it, existing chats, history and files carry over automatically to the updated experience [2].

For Connections Boardroom, pick a scene, seat a few advisers and say the first thing on your mind [3]. The Boardroom is for paying members, so a free Connections member has to upgrade first [3]. The sign-up steps are not covered here, so check the first screens before you commit.

Things to check before you choose

Ask whether you need the tool to read your files. ChatGPT's free version has limited file uploads, not quantified on its page [1], and Connections Boardroom takes a PDF, a Word document or a screenshot [3].

Ask which devices you use. Microsoft Copilot needs iOS 26 or later on iPhones [2] and Android 13 or later on Android phones [2]. ChatGPT lists web, iOS and Android access for its plans [1]. Connections Boardroom runs as a standalone web app [3].

Ask how each tool handles your conversations. Microsoft Copilot keeps work and personal conversations separate [2], and ChatGPT's page says data is encrypted in transit using TLS 1.2 [1]. Ask what each tool costs once you need more than a free option, because this page does not publish those amounts for ChatGPT or Microsoft Copilot [1] [2].

Ask whether you need a record of the discussion. Connections Boardroom saves each meeting as a transcript [3].

How to choose

ChatGPT's page describes its intelligence for everyday tasks [1]. Microsoft Copilot's page says work and personal conversations remain separate, with history, files and protections tied to the relevant account [2]. Check the account setup to confirm that separation for your own use. If you want to use Word, Excel and PowerPoint for free on the web, Microsoft describes that option [2].

If you want a set of AI advisers to answer and argue over your plan, with minutes and a plan written afterwards, Connections Boardroom does that [3] [3]. The Boardroom is for paying members only [3]. Connections Free costs $0, and going over a limit stops the feature rather than billing you [3].

Frequently asked questions

Does ChatGPT have a free version?

ChatGPT's free version is available to everyone [1]. Its page describes intelligence for everyday tasks [1], and lists image creation [1], file uploads [1] and deep research [1] as limited, without giving numbers. The paid plans are Go, Plus, Business and Enterprise, priced per user per month [1]. This page does not give those amounts, so check ChatGPT's pricing before you decide.

Is Microsoft Copilot free with a Microsoft account?

Microsoft Copilot is free with a signed-in Microsoft account, and its page says a free tier is available with one [2]. Some capabilities are subject to usage limits, and more are available through paid plans [2]. Microsoft 365 subscriptions include the Copilot app and additional premium features [2]. This page does not publish those prices, so check Microsoft's current pricing before you decide.

What does Connections Boardroom cost?

Connections Free costs $0, and going over a limit stops the feature rather than billing you [3]. The Boardroom is for paying members only, so a free Connections member has to upgrade to use it [3]. Connections Pro, the first paid plan, is $39.99 a month and adds premium features across every Connections product [3]. Connections Business is $99.99 a month, with higher limits across every Connections product [3].

Can Connections Boardroom read a PDF or Word file?

Yes, you can drop a PDF, a Word document or a screenshot into a meeting, and the advisers read it [3]. Meetings use up your Connections AI usage [3]. You can also dictate using your browser's speech recognition, and each reply is spoken aloud [3].

Does ChatGPT or Microsoft Copilot work on a phone?

ChatGPT says its listed plans support access on web, iOS and Android [1]. Microsoft Copilot is available on the web, desktop and mobile [2]. It needs iOS 26 or later on iPhones [2] and Android 13 or later on Android phones [2]. Connections Boardroom runs as a standalone web app [3].

A plan in the product file is named Connections Pro. [3] Creating a board member costs one credit. [3]

Try Connections Boardroom

Sources

  1. ChatGPT, chatgpt.com/pricing, read 2026-10-08
  2. Microsoft Copilot, copilot.microsoft.com, read 2026-11-01
  3. Connections Boardroom's own description of itself (the product of this site's publisher)

Related comparisons