Travel system strollers suck. I'd rather spend $300 on a good stroller and use a convertible from birth than be stuck with a crappy stroller. How about Valco Snap4? Go through ebates and shop.ca and get 15% back.
http://www.shop.ca/m20/c/valco-baby-snap4-SNP0392-22403661
And you could get a Graco car seat through there too with 15% back and maybe be closer to your budget? Looks like the Graco adapter is out of stock on shop.ca but you could get it elsewhere.
There are other strollers as well. The baby stuff ships direct from reputable baby stores. One being Snuggle Bugz.
SO agree with this. Do not get a travel system package like any of the Chicco or Graco boxes at BRU. The infant carrier will be solid, but the stroller will be a throw away in frustration if it didn't break before it.
We got the Britax B-Safe carrier recently and it clicks in perfectly (they make an attachment) with our 3+ year old Baby Jogger City Mini (the B-Agile is a competent copy of this stroller w/o the need for an attachment). That stroller is a tank, lasts forever, light, is INCREDIBLY easy to fold and store, and will be the only stroller you will really need until the kid outgrows the need for a stroller (i.e. like 6-7 years old...they still like it if you go to Disney World or something where they have to walk a lot...long day at a park, etc...not to mention another child down the road).
There are some deals out there...so if you can figure out what you want, then be on the look out for the best deal. I can say with confidence, you can get these two items for right around $300-$350 if you look hard enough. With the ONLY caveat being that this is based on US pricing which I think is lesser than Canada. You will keep your AWESOME stroller for a lot longer and use it for multiple kids.
The only other option would be to get an infant carrier and a frame stroller for the time being to span out your big purchases. Then buy the nicer City Mini type stroller months from now. Frame strollers just snap the infant carrier in, have a basket, and don't take up a lot of room. They are a little more difficult to collapse and such, but it's basic. Should cost you around $200 for the two.
Just don't buy a travel system stroller.