I think it would be very rare if you were to find a business or restaurant that would only give you C$1 for one greenback (but I am sure they exist), so to avoid this possibility, change your money at an exchange outlet or bank to ensure you get the going rate.

Winnipeg is far more economical than most other cities in Canada for most everything and as for food and accommodations, your travel dollar will certainly go quite a way.

You could probably get a room at the Fairmont Winnipeg or Fort Garry (both superior properties) for a around C$130 not taking into account CAA/AAA or other possible discounts, which would be about US$90. My choice would be the Fort Garry

http://www.fortgarryhotel.com/

You might want to run the $30 hotels past some of us as it might be hit and miss on value for money.

Safe travels and say hi to my Mom