One good way is EasyJet – Glasgow to Berlin is the one we took, but there are others. The UK has high taxes, but I think you can likely get a flight for less than $100 CAD total. The cheapest flights are cheaper elsewhere in Europe.
 
Check www.whichbudget.com .
 
It doesn’t really matter which city you go to – you can enjoy that city and then make your way to Munich, either by train or whatever method.
 
I’d suggest booking your Oktoberfest accommodation way in advance, like even now.

Generally, I would head further south as winter approaches. Maybe start with some place in the north (London, Stockholm, Amsterdam?) and work your way down to Munich. Then maybe head to CH, AT, then south to Italy or Croatia or Greece.

For flights, have a look at www.canadian-affair…. and www.flyglobespan.ca as well as www.bookingbuddy.com — the latter can search Flightcentre, Mobissimo, Expedia.ca, Kayak, and others.

my advice is to try and book flights as far in advance as possible.  There are many cheap flights available and there are a number of price comparison websites that you can check when you arrive in the UK – here’s just one example http://www.travelsup…

good luck