Recently, as I contemplate my life in this soulless dystopian tech city, I cannot help but fantasize about Chicago and how awesome that city really is. So underrated. The only true negative is the winters. Consider the following:
- Very cheap for a major city, especially rent. There are amazing luxury highrise apartments everywhere, but the rent is still below not just NYC and SF but also Seattle, LA, Boston, DC. The city is super affordable on all aspects.
- Only U.S. city aside from NYC where you really don't need a car to get around. Yes, other cities have public transportation systems, but they are not as well developed and comprehensive. Chicago is truly urban in this regard.
- Amazing restaurant and nightlife scene. It's world class, just below NYC. You have everything from upscale lounges in River North to Big 10 sports bars in Lincoln Park and hipster dive bars in Wicker Park and everything in between. The restaurant scene is massive, with enough diversity to keep you engaged for years.
- Urban beauty and aesthetics. The downtown core and the surrounding area is stunning, as it straddles pristine Lake Michigan, with Lincoln, Grant, and Millennium parks nearby. One can go jogging or biking on the trail right next to the lake, a trail that extends more than 10 miles. You also have North Avenue and Oak street beaches, where you can play beach volleyball, grab drinks, and hang out. The city is very walkable and clean, as there are no garbage bags lying on the streets.
- Incredible summers. Best summer city in the country. It's plenty warm but not too humid (far less so than NYC and obviously the South), and the social scene is out of control, as everyone is out and enjoying the summer: Cubs games, outdoor festivals, rooftop parties, daydrinking at outdoor bars, lounging by the pool, and so much more. Words cannot describe how awesome Chicago summers are.
- Dating scene. I have to admit that it's not as good as NYC but a close second. Plenty of beautiful fit women and a vibrant singles scene.
- Midwestern humility and culture. Despite being a world-class city, it lacks the elitism of NYC, the superficiality of L.A., and the obnoxious ultra-liberal sanctimony of Seattle and SF. For the most part, the people are nice and down to earth. Although the city is liberal, the people don't obsess over politics; very rarely will you meet a woman who asks about your political views on a first date. The city is quintessentially All-American.
- Fantastic work-life balance. People here just don't work crazy hours. Even in finance, 80+ hours are virtually unheard of. People are out of the office by 7 PM for the most part. This allows ample time to actually do stuff on weekday evenings.
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