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Jazz is chill
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The Pilot
Located in Yorkville. If you go and decide you're not into it, there are many other bars and restaurants on this strip.
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our budget isn't quite up to par with the rest of 2p2.
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Then Yorkville is def not an area you'll want to hang.
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If you're going for drinks, as opposed to shopping, Yorkville is fine. You won't pay any more for a pint of beer at The Pilot than you will at most other uptown pubs.
And to be fair I balanced it out with The Silver Dollar where you can drink on the cheap. When you leave the Dollar walk south down Spadina and head west on College - tons of good little bars with patios and most of them will have live music and affordable drinks - Rancho Relaxo, Oasis are a couple I remember.
OP was also asking about strip clubs. I can only speak to The Brass Rail (also on Young just south of Charles). Go in for a beer or two and check the place out. The chicks are the hottest of the hot but the place is tiny and the drinks are very expensive.
If you're looking for an after hours bar I can give you directions to The Matador. They open at 2 AM and they have a rock and roll house band that plays until around 5 AM. It's a police / biker co-op so you don't have to worry about the place getting busted. The bar only sells mix but you buy your booze from a lady in an elf hat who sells bottles of vodka, rum etc.. out of her satchel... honest. It's a pretty cool operation. Warning though... the dudes outnumber the women around 2:1 - good party though.