Montreal & Quebec City?

[Presh]

Hi
I am planning to travel to Montreal and Quebec City the last week of September this year. Any tips and recommendation (such as, nice-but not so expensive-hotel/b&b in great location)? How many days should I spend in each city? I am also thinking to visit my friend in Calgary. Also, I have to be in Chicago for few days before travelling to Canada. Pppffffff... I am still not able to decide how can I manage my multi-destinations transportation. Budget wise, is it better to fly to Calgary/Montreal from Chicago and return to Chi or NY by train or bus (with worth seeing scenery?) to catch my flight back to SG?
Anyone happen to be there too during the same period? I know, bunch of questions I have. Thank you all in advance.

[beenhere10years]

You are very fortunate. The leaves will be magic in Montreal/Quebec that time of year. In fact, it is an extremely busy time for them as they are inundated with 'leaf-peepers'. Better make you reservations ASAP.

OK. Not sure if I can really help you out here but I'll try. You'll want more time in Quebec. Montreal is lovely but Quebec City is very special.
The food! Coffee in huge bowls! Crepes filled with everything you can imagine! I think I had the best Italian food of my life in the Old City. There are lots of petit auberges (little inns), find one near the old city if you can.

The scenery from Montreal to NYC can be lovely, but that's a long trip on The Montrealer (12 - 14 hours I think). Better to fly if you can. Look into budget airlines like JetBlue, Ted and Independence Air which don't penalize you for one-way travel. Calgary is a long way, can't your friend come and meet you, then you'll have a buddy to split expenses with.

I think you should find the cheapest flight to either Chicago or New York and cobble together the rest of your trip from there. Try an around-the-world ticket. They have restrictions but can be much cheaper. Hope this helps,

BH10Y