North44 ($100/head easy)
Old Mill ($60-$90)
Marcellos (St. Clair West/Dufferin @ $30/head average)
Kum Jug Yun (I can't remember the actual spelling, its on Spadina south of College on the east side next to a Grosmans Tavern...locals joint Chinese BBQ, $5-$10/plate)
Country Style (Bloor St, east of Bathurst, locals joint Hungarian food, awesome schnitzels, $13/plate last I was there)
I can probably name a lot more but I'm having a hard time bringing them up to my mind and I regular at these places.
Island Foods on King just east of Dufferin has the best boneless chicken roti I have had in my life. Two people can eat for a little over $20 depending on what you get. It's a cross between fast food and a sit down place. You order and pay at the counter and they are licensed so you can have a beer or whatever with your meal but I usually stick to my diet coke and a bottle of water when I eat there.
The Bright Peal in Chinatown (it's on Spadina but you enter on a sidestreet then go upstairs to the restaurant) has the best Dim Sum! They serve it the traditional way with the carts. The servers bring the carts by your table so you can take what you like. The tea they serve is wonderful too and I've always left there feeling well taken care of and of course well fed. The last time I was there it was just my daughter and I (we were having a girls day in TO) and our meal was $25 for the two of us.
For pub grub I like the Elephant and Castle on King Street West, and also the Brazen Head on East Liberty Street. The Brazen Head is a little more expensive than the Elephant and Castle but still it's nice.
We went to Shoeless Joe's on King east of Dufferin a few weeks ago for the first time and I was pleasantly surprised. We were a table of eight and I know that big tables can be a challenge for the kitchen and servers but they handled it well. The kids' food all came first and that was fine with us, and then not even five minutes later the adults' food arrived so we were all eating at the same time. Prices were reasonable and the only thing you need to bear in mind is that it's a sports bar so the experience in the evening would be very different to what we had at lunchtime.
The Old Spaghetti Factory on The Esplanade has always been a favourite of mine. It's one of the places my husband and I used to go to when we were dating and then when we had the kids we loved taking them there for dinner. Prices are reasonable (around $20-25 per person) but I haven't been in a few years so I can't speak to the food quality today.
For fine dining I would suggest:
-Ruth's Chris Steakhouse (on Richmond West in the Hilton Toronto Hotel) Prepare to spend at least $100/per person but the food is amazing
-Harbour Sixty Steakhouse (on Harbour Street, just past the off ramp from the Gardener Expwy) Again you're looking at at least $100 per person just like Ruth's Chris. I prefer the side dishes that Harbour Sixty offers compared to that of Ruth's Chris but both are equally good.
-Rosewater Supper Club at 19 Toronto Street is an amazing venue and I recommend it for that alone.. we have been there a number of times and the quality of food and service has been varied. I tend to order steak when I eat out so for me my dining has been good but we always go with the same group of people and others in our party have had disappointing meals at times. Plan on spending at least $100 per person to dine here as well.
For fast food it depends on my mood... I love Popeyes but catch me at the right moment and you will find me in Harvey's with a bacon cheesburger and a poutine! Lick's is good and I really do like the Pita Pit as well.
Bright Pearl is good, a bit touristy and a little pricey crowded with guai lao compare my normal haunts. River Seafood on Gerrard and Broadview has excellent dim sum, 3 people can eat generously for $30, its small but you'll never have to wait for a table, and the ladies there surprisingly know a lot of English. I usually go to Sky Dragon only because its easier for me to get to and their Sunday happy hour lasts longer.
I went to Ruth's Chris some 15 years ago, perhaps longer. It was easily $100/head, nice to see nothing has changed there. Everything was a la carte. I'd suggest the Keg Mansion on Jarvis for better value.
My mother told me of a place on Ossington and College called Phils that does some wicked BBQ and the only place in town I can think of that does pulled pork albeit a bit on the pricey side, around $25-30/head. Come to think of it, that area has become a hot bed for good eating.
I forgot to mention the Keg Mansion.. I've enjoyed it every time we've been there. I don't think it's there anymore but the Old Fish Market on Esplanade was good as well.. the last time I was there was seventeen years ago and I was in the beginning stages of labor with our son. I had the stuffed mushroom caps for an appetizer and then didn't feel so great so I had chicken fingers and fries as my entree..
Kom Jug Yuen is f'ing AMAZING! I lived literally around the corner when I was going to school in TO. I probably ate there upwards of 3 times a week. Also Musa on Dundas West. It's just west of Bathurst and Dundas. Awesome brunch. I have never actually eaten there for any other meal. Gilead Bistro in Corktown is one of Jamie Kennedy's places and is garnering some pretty good reviews. Food Arts had hailed him as the Alice Waters of Canada. I actually worked there for a couple of few weeks after I graduated school and had a single morsel of food that was so flavorful it's what I use as a benchmark up to today. In short go there and eat.
I finally had the chance to hit the Old Spaghetti Factory. Unimpressed.
Its a tourist trap, always busy with people from out of town and not too many locals will hit the joint. Parking is a pain and pricey plus its just south of the financial district meaning regardless of the directions you take, severe traffic will ensue. Food comes in very small quantity for the price you pay; I had the fettucini alfredo with a grilled chicken breast (3.5oz precooked chicken breast, 8oz pasta, 5oz sauce), dish was just under $20 before tax. I don't work too far away from the place, we share suppliers as I know a couple drivers doing drop offs on me asks directions to the OSF so I knew what was in everything. Could easily eat better in Little Italy for at least the same price if not cheaper.
Found another great place, Green Eggplant. They've got 2 locations, Eglinton West and Spadina that seems to have an older crowd. I was disappointed to learn they didn't do the restaurant's specials there. Location 2 is in the Beaches area, Queen and Woodbine I think. Servings are huge, I swear I saw a salad that must have been served on a 32oz plate piled high. I recall none of the salads being over $8. They do chicken sewers, easily 12oz worth of white meat, that are awesome. My uncle's girlfriend had I think a teryaki salmon, 2x10inch pieces. Most of the main plates went for $15-$20/ea. Only gripe are their sides; rice is lumpy and flavorless, fries don't get tossed so they come lumped together. They also do a pretty mean goulash.
Headless, it sounds like OSF has changed alot since I was last there. It was a while ago (both kids were under the age of 7) and we did enjoy our meals. I can see it becoming (and likely always has been) a tourist trap just based on the decor of the place and I know the area it's in really sucks for traffic. When we would go to that area, we would take the TTC to Union and then walk over.. it was much less stressful that way.
I don't know if they have expanded into Toronto yet but Bombay Bhel has two locations.. one in Mississauga and the other in Markam and their food is very good. Prices were average for an Indian place and they have very good naan bread. If you have a way of getting out to either location it is worth the trip. The Markham one while it has seating, it feels like a takeout place, but the Missisauga one is much more intimate. (I suspect the one in Mississauga was the original one)
Got another great place to recommend, http://www.positanorestaurant.ca/ on Mt. Pleasant North of Davisville. Very small and quaint restaurant, you'd probably pass by it without giving it a second thought. Excellent food, we went as a party of 4 and had a beautiful antipasto della casa that included grilled veggies, olives, buffalo mozzarella, all with some really thick aged balsamic. I recall they do some seasonal menu, I had their veal chop that I don't see on their regular menu.
The Black Hoof on Dundas West is good, cool with interesting offerings, if you like meat, offal and charcuterie. Shameless plug, but if you don't mind forking over some cash George restaurant (where I work) on Queen near Jarvis is pretty good too.