The driving distance from Winnipeg to Calgary is 825 miles (1329 km) and depending on the conditions of the road, i.e Traffic or construction, the journey should take around 14 hours. However since you may be planning to make stops along the way this time would be significantly longer.
The route i imagine you would take would see you driving through Saskatchewan and Alberta
In Saskatchewan you can choose from a range of casinos, spas, great shopping areas and restaurants – you’ll keep as busy as you like. If you prefer the outdoors however you could do some canoeing, kayaking, hiking, biking, boating, camping, horseback riding, wildlife viewing – the list goes on and on
In Alberta you have the well known tourist destinations Banff National Park and Jasper National Park. The two mountain parks are connected by the scenic Icefields Parkway. 5 of Canada's 13 UNESCO World heritage sites are located within the province: Canadian Rocky Mountain Parks, Waterton-Glacier International Peace Park, Wood Buffalo National Park, Dinosaur Provincial Park and Head-Smashed-In Buffalo Jump.
When arriving in
Calgary there is so much you can do! Many people travelling to this area like to experience the wild-west flavor of the city. A good start on your Calgary tourism trip is the Bar U Ranch National Historic Site. This historic site is actually an hour southwest of the city, but gives a great insight into what Calgary Canada might have looked like 100 years ago. There are 35 original buildings still standing, some dating back from the 1880’s. You can take a tour of these buildings.
Also there are markets, and several parks, your days could easy be filled by enjoying your surroundings. There are tours avavilable and you could contact Calgary Tourism to see whats available or simply get some local maps and do the exploring for yourself.
You havent mentioned if you have accomodation booked already but you could check out the link below to see what is available.
http://www.destination360.com/north-...ary-hotels.php
Sounds like it could be a fantastic trip!
Winnipeg to Calgary 
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