How do I sync 'on my mac' calendar in ical with icloud or an alternative for my iphone?

I'm using Outlook 2011  with 2 IMAP email addresses, a business email and a gmail address.  The only reason I'm using Outlook instead of Mail, Address Book and iCal is because there were issues with me receiving meeting invites from business colleagues.  Anyway, now I'm using Outlook, my contacts & calendar are no longer synchronising with my iPhone (4).  I'm using the Outlook synch services to copy the Contact info to Address Book and the calendar info to iCal. BUT, the calendar in iCal is 'On My Mac' and doesnt get picked up by iCloud. 
Can anyone help with simple suggestions for a wireless solution for keeping Outlook calendar in synch with my phone?  Would upgrading my email account to Exchange be a solution?

Thanks Winston.  I'm aware that the 'on my mac' calendar doesn't get picked up by iCloud.  I'm wondering whether anyone can help with the best alternative solution for synchronisation of phone and Outlook.

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