I don't know of any late-night deals, but there are often cheap set menus/special deals on wine on Sundays, Mondays, Tuesdays and Wednesdays (Union, Ascari Enoteca, Porzia - Monday nights 1/2 off wine, Brockton General - Weeknight prix fixe, Beast - Wednesday 1/2 off wine etc).
Summerlicious will be on when you're here in July (I think?), not everyone on the board likes it, but there are some good deals (Luma, Canoe, George, 93 Harbord, Drake, Globe are some of my faves).
Brunch/Lunch is a good option for saving. I like Luma for upscale downtown.
Harbord Room would be nice for your more celebratory dinner and you'll get a great experience there without food that's too fussy.
For Mexican there's been a rash of tacos - La Carnita (now doing brunch), Grand Electric (also doing lunch) and Playa Cabana (takes reservations!) are the top three, but Seven Lives in Kensington is a good option as well.
There may be food truck events when you're here - follow them on Twitter to check.
For comfort food, Caplansky is near Kensington. Or for upscale pub comfort food you're very near The Queen and Beaver. You should also check out The Gabardine on Bay.
There's okay ice cream at Ed's in Leslieville/The Beach, but you're better of with gelato uptown (Gelatiere, Simply gelato) if you like frozen treats.
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