One of the CRAZIEST Hotels I've Been To! (The Waldorf Astoria Chicago Review)
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This is some old school, balling out like a Rockefeller or a Kennedy level shit. This is some you aren’t sure if you’re allowed to be there if you’re black, Latino or Asian level shit (but fuck it, this person of color Editor-in-Chief loves fuckin’ with white people’s heads by booking a room here).
The Waldorf Astoria Chicago looks like some place where the Great Gatsby would hang out. Marble floors, deep soaking tubs, tv’s in the bathroom, everything classy and understated while simultaenously screaming “I’m fucking killing it by being here!” This hotel has been named one of the best luxury hotels in the country by a ton of different publications, including Travel and Leisure and Conde Nast Traveler. It’s definitely on the Baller Hotel Bucket List (article coming soon!) If you take a girl here, you’re definitely getting laid — but she’s probably gonna want to lock you down after!
The suites are huge and come with a really chilled out living area. There’s a quality fitness center (just because you’re on vacation doesn’t mean that you should be taking time off from the gym) and one of the nicest pools I’ve ever seen, with some nice seats to lounge around in by the pool. It’s hard not to feel like you’ve made it when you’re swimming in this while the Chicago skyline zooms by you on either side:
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About the only thing that isn’t amazing here is the bar: there’s only one tiny bar that looks like a hidden-away parlor. The bartenders are friendly and the drinks are stiff, but the crowd tends to be middle management consultants with their wives — not really the baller environment the hustlers who read this magazine usually go for. That being said, it’s fun hanging out at the bar and thinking about how hard those middle aged chumps have to work to afford shit like this, while folks like you and me who like to hustle get the same lifestyle while goofing off and having fun. Plus you never know — maybe you can get lucky with that chump’s cougar wife. After the way their Baby Boomer generation fucked our Millenial generation, it’ll be some apt payback…
WHO TO TAKE WITH YOU: Some girl you’re REALLY trying to impress — if you’ve convinced her you’re a billionaire, this is a good way to keep the illusion going. Also a great place for a staycation or a personal getaway when you really need some time to remind yourself how much of a baller you are.
ATTRACTIONS NEARBY: Shopping on Michigan Avenue. The Art Institute of Chicago is a short Uber ride away, and is my personal favorite art museum in the US (check out Sunday Afternoon on the Island of La Grand Jatee, aka where Ferris Bueller took Cameron on his day off).
FOOD NEARBY: Lou Malniati’s for deep dish pizza, of course! (Totally worth the 20 minute wait for them to make the pizza fresh) Or take an Uber to Girl and the Goat to have a really amazing feast.