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Churchill is fantastic. In every trip I have had pictures of at least 10 bears/ sometimes 30. Go very late October or Early November. Smaller bears are more plentiful earlier in October but as the bears congregate waiting for the ice to freeze the little ones disappear and the males play spar. August has very nice pictures too with flower and bears but for that I suggest Nelson House, MB (http://www.churchillwild.com/adventures/great-ice-bear-adventure/ . March has baby bears coming out of the den's but its at -40 and they are hard to find and even more expensive to arrange. For fall, the later the better for bears but as soon as the ice freezes they are gone onto the ice looking for ring seals (they have not eaten in 6 months) so not later than Nov 15 is my advice.
Going to Churchill is expensive. $1500 return from Winnipeg to Churchill. $500 return to Winnipeg. An overnight in Winnnipeg $150. $150/night in Churchill. $400 per person per day on tundra buggy. Thus a 2 day trip would be $3000pp. There is very little to do in Churchill in the evenings and aurora shooting should be done with much caution because the bears wander through town ( and did I mention that they have not eaten in 6 months).
I am limited in time so what I do is book with http://www.classiccanadiantours.com/ and they have a tour that leaves Calgary at 6am and returns the same day at 9pM for about $1700 (737 1.5 hour flights). Occasionally I ask them to leave me there and I catch their return the next day for another $1000 or so (cost $400 for tundra and $100 for hotel so its a great deal). You have to ask them for this ability. They probably call it the Stoness deal ( ) So for $2700 you save $300 or $1000 and a day. They have a terrific tour. If you go I will give you tips about where to sit etc. On balance this is a really good deal for time and money if you are only going for 1-2 days.
It is very family friendly with lots of old people and young people taking the trip of their life from Calgary. It also runs from Edmonton.
I am going with this tour operater Saturday to Prince Rupert for Grizzly and I have been with them on about 5 trips to Churchill so far.
Alternatively, contact Calm Air for flights from Winnipeg, I stayed at Aurora Inn last time and it was clean and warm and friendly. Tundra buggies is the recommended operation because they have a better spot on the beach in my view. There is a hotel with their own bus but last year they went to a spot on the beach with very few bears. It could be just an anomoly but give the price and time I woudl go with a large buggy operator. Make sure you understand the weight/cargo restrictions on Calm air before booking.
Each of the buggy operator's have a lodge (mobile home on wheels). I am not sure if it is a fair conclusion but I concluded that it was not worth it since its lots more than aurora inn and its mostly dark when you are there and you can't get out because of the bear risk.
You can also drive to Thompson and take the train to Churchill but it runs at about 15miles /hour and takes forever and you woudl have to check to see the latest leave time in the season.
Churchill is wonderful and worth it. The bears are fantastic. If you follow my smugmug link in animals you will see some of my polar bear pictures from Churchill [green smiley face under my icon is the link]
I would leave the 2 year old at home (he/she will get in the way of pictures and its cold and you need to be quiet which is likely the reason they do not accept under 8).
I would bring a 500mm or bigger. Rent a 600 is best because you are up high and if you get a long lens it does not look high but if you have a short lens you will only get shots looking down on the animal. Expect to hand hold because the people shifting on the buggy make monopod not work. I have gone with a 100-400 and I consider this the minimum lens you should take.
The polars show up at the sled dog area and a local might take you there to view but don't go anywhere without a car close to you.
PM me if you have any questions. I am from Northern Manitoba and have a passion for this area.