Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Winnipeg to Mount Kilimanjaro as you normally would.
If you book a flight to Mount Kilimanjaro from Winnipeg, you will be flying from Winnipeg, which is the city’s only airport. Winnipeg (YWG) is located 7.3 km from the centre of Winnipeg.
These are just IATA (International Air Transport Association) codes. They are used in aviation to identify and differentiate airports. That’s why a Winnipeg Airport to Arusha Kilimanjaro Airport flight would often be abbreviated as a YWG to JRO flight.