I hate to be this guy but I just wanted to check in on Streeterville because I actually like Streeterville a lot. Particularly as my #1 hotel destination within Chicago because it’s easy to get to Wrigleyville but centrally located for walking.

You got a bunch of awesome bars off in/around Chicago Avenue up into Gold Coast’s Viagra Triangle. It’s close to Michigan avenue for day time walking and of course all the action in River North, but at a major discount for quality. So personally speaking, I actually like Streeterville a lot and think it’s one of the better areas of Chicago as you get older.
The only problem is that Chicago leadership doesn’t give a shit about Streeterville or anything around it. They see it as a place for rich people that doesn’t need to be policed because Northwestern Medical Security is already all over the place with the hospital. So they started sandbagging city services and now about a decade later, the place is completely up for grabs around the clock. From car jackings to violent assaults and unruly teenage mobs. Streeterville is perfectly symbolic of Chicago’s collective nosedive. It’s a place that used to be awesome, should be better and will probably suck at an increased rate for at least the next decade.
MEANWHILE
Property taxes are up 89% over the last 20 years with a rapid increase since the Chicago Teachers Union completely hijacked local politics. Bunch of fucking jabronis running that union if you ask me.

Anyways – it’s a good time to be positive about Chicago because it’s simply too easy to be negative. I know that sounds backwards but my point is I can’t fall into the herd mentality of these basic criticisms that Chicago is falling apart.
Truthfully – leadership is downright pathetic. Something as a kid that you don’t really understand but now as an adult, it legitimately makes you puke when you think about the men & women that are tasked with making Chicago a better place. They’re all such assholes. Literally every single one of them.
But that doesn’t mean we’re hopeless so much as it just means we’re completely fucked right now with how things are currently being done. And unfortunately nobody worth a shit will come anywhere near this catastrophe any time soon. So don’t waste your time getting romantic about some salvation-wielding mayoral candidate.
Realistically it’s just going to take a lot of time and turnover, and ultimately divine intervention from whoever slays JB Pritzker’s communist agenda.
Until then I think the best we can do is 3-fold:
- try not to get robbed
- enjoy the food
- tip your local bartender