I've been to Vegas many times. I used to alternate between Vegas and WDW every year for my "winter" vacation. LOL I favour Orlando more than Vegas these days. However, that being said, I was just there in May.
There are hotel deals EVERYWHERE right now. If you're not buying a flight/hotel package and doing it separately (you need to price it out to see which is cheaper), go to the hotel sites directly and see what kind of deal you can get. I've been getting emails from Luxor and Treasure Island telling me of really cheap nights. Both are pretty nice hotels. Hotel rooms will be more expensive on Friday and Saturday nights. If you're not going for a week, consider missing the weekend and stay on the weeknights. It'll be a LOT cheaper that way.
I used to love staying at Ballys since it had really big standard rooms and was in the centre of the strip. Last time we stayed at the Las Vegas Hilton (a little bit off the strip) for one night before we moved to a timeshare. I've stayed at the Flamingo ... it's a bit old and showing it but it's still ok. It has a very nice garden in the back with birds, ducks, flamingos, etc. Luxor and Treasure Island have very nice rooms (the pyramid rooms at Luxor are interesting!)
We usually rent a car when we go ... mostly so we're not stuck on the Strip. We like to drive to the State park, the desert, to other casinos, to the outlet malls, etc., etc. When in Vegas, you don't have to in the casinos all the time. If you don't want to rent a car, check out the various shuttles to the outlet malls and to casinos off strip.
Cheap eats are everywhere but not all cheap eats are good. LOL Stay away from Circus Circus food and rooms if you value your lives. It's ok to wander in and look around but don't stay there or eat there. If you want some good value and good food, go to Ellis Island. They have a nice restaurant AND they also have their own microbrewery and bbq restaurant. They have an enormous rib and chicken dinner that is under $15....and it is delicious.
The outlet mall south of the strip (it used to be a Belz but it's called something else now) has a Character Warehouse. You can get discounted
Disneyland stuff there. It's hit and miss. One time I hit the jackpot there and got DL baseball caps for $2 each. Alas, my last trip, there was nothing there that I really liked. It's worth checking out though.
On our May trip, we actually flew from Toronto to Calgary to Vegas. (The direct flights from Toronto that were cheap arrived late in the evening and we didn't like that.) I can't recall how much the Calgary to Vegas leg cost but I'm pretty sure it was a lot higher than $102 or even $188.