Thought I'd go back and put in some summaries to summarize the trip/areas.
Drive, this is a long and fairly boring drive from Toronto. Roughly 9 hours, I'm not sure we would do it again. Even with the initial stopover at the outlet malls, doesn't seem worth it. If I went again, I would probably opt to fly depending on the cost.
Food, the food was really good here. Props to Mike taking the time and effort in finding the places and thanks to Alex for actually getting us a reservation at Girl and the Goat. No complaints about any of the places we stopped at for snacks or meals.
Accommodations, the place was okay. The area could've been a bit better, but the price was pretty good for the city especially since it included parking (parking in this city is ridiculous.
Regrets, I wish we could've done the boat cruise. It looks like it would've been interesting given how unique the architecture in the city is.
Disappointments, deep dish could've been better, but that may be because we didn't go to the better pizza joints in town. Next time!
Highlights, definitely the food and architecture.
Costs, accommodations worked out to about $81 Canadian for 3 nights, car rental + gas was $89, plus food and other things.
Would I return, yes. The food and architecture is worth another visit.