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Desktop Outlook
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In Outlook, select File > Open & Export > Import/Export.
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In Import and Export Wizard box, select Import an iCalendar (.ics) or vCalendar file (.vcs), and then Next.
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Select the calendar file from your PC and select OK.
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Select Open as New. The items are automatically imported into your calendar.
Outlook Web
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Locate the calendar you want to add and save it to a folder on your computer as an .ics file.
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Sign into Outlook on the web.
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Select Calendar
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In the navigation pane, select Add Calendar.
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Select Upload from file.
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Select Browse, choose an .ics file, and select Open.
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Select a Calendar to add to
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Select Import.
Microsoft References:
Import Calendars into Outlook
Import or subscribe to a calendar in Outlook on the web