Hey, just reporting back in. Here's my takes from my visit. Just to thank you guys, and give anyone else planning a visit some insight.
Okay, first day the first three things I did after checking into the hotel was walk down Magnificent Mile, a burger at Gibson's and then went on the Architectural tour. Literally, couldn't have asked for a better kick off to the city. Went that night to RPM Italian which I would strongly recommend to anyone who hasn't been, and unless you are really chasing the high-end steak or seafood is well priced. Day two, hit Wrigley, walked to Pequod's (but couldn't get in) went to Al's Beef, and went to Signature Room at night, . Third day, hit Lou's, top of the Sears, the Art Institure of Chicago to see Van Gogh (unreal collection), and go to the White Sox game. I'll say this, Wrigley the Stadium has character (although a ton of obstructed views), White Sox's fans have character for better and worse (hope no one takes offense). I don't think anywhere else I've seen unlicenced liquor sales of shots before a game (and I've tailgaited at Browns and Bills games), so since I've been to Fenway, in many ways despite going to Wrigley, Comiskey was the most unique baseball stadium experience I've had. Despite the loose laws outside, it def felt like the strictest inside stadium experience (The Cell nickname may have multiple connotations), but the food was good (to try to experience more of chicago, I just got one Polish sausage and one hot dog from Vienna Beef) and the options around looked amazing. Finally, today, I hit Pequods with an early reservation and then walked Oak Beach to Navy Pier and back.
In totality. While Signature Room was a cool experience, especially because I sat on the south side of the building looking at all of Chicago and the food was good, the support staff outside the waiters felt like they were trying to rush me out. Amazing place to see once, but I didn't think it was fine dining. Now, RPM Italian is amazing, and makes me want to go back to every other RPM whether Seafood or the Steakhouse. I only ate there for lunch and drank at Gibson's bar (went once for food once for drink), but I'd love to check it out again, the staff there was amazing. A waitress there gave me a list of things I need to check out if I ever return (Little Chaval for Burgers, Luke's Italian Beef, etc).
In short
-Italian Beef is a must try (pick your spot). I loved Al's. (oh and for outsiders go all out, get the spicy giardiniera and dipped)
- Pequods is great, but I've had similar in Toronto, while Lou's may not be better, it is more unique. And, whoever said here that Pequod's is more Detroit style, after trying Lou's, I agree.
-unfortunately couldn't get to Jimbo's.
-I feel Toronto always gets compared to Chicago good and bad. I will say this, Your waterfront and parkspace makes me ashamed of what we've managed to do with ours, and we don't have anything that touches magnificent or park allocation on the positive front.
As expected, while I feel I accomplished most of what I wanted to do, I am itching to return. Thanks to everyone here who helped give advice. Especially
@Paul Allen and
@ChiHawks10 I didn't think an American city could surpass NYC, and while I'm not sure you did, you guys are seriously 1A and 1B of American cities I've visited. Thank you again to everyone for all your help in helping me figure out what I should do.
Fortunately, I now need to return to try some of this infamous thin crust, some of the mexican food, and some of your burger joints on top of enjoying a truly world class city.
edit: Thanks again, threads like these have helped me for multiple cities. Unfortunately, for whatever reasons the Leafs board doesn't have this, if anyone here sees this and is visiting Toronto, please DM me, threads like these have helped me have great experiences in cities, and I'm more than glad to return the favor for anyone coming my way.