I wasn’t born here, but I’ve lived here longer than I’ve lived anywhere else, surrounded by culture, high fashion, awesome beaches, and some of the best food I’ve ever had in my life. Chicago is the textbook definition of a world-class city. It’s filthy and industrial, lavish, and ridiculously extravagant…to quote Sinatra, it’s definitely “my kind of town”. It’s not for everybody, but in my book, it has everything. It is rich and poor, clean and dirty, corporate and industrial, and yet, overflowing with tourists. But more importantly, it’s overflowing with jobs. If you want to work, you’ll find work here. It’s uniquely Midwestern in that unlike New York, this city sleeps. Not because there’s nothing to do. You can always find food and entertainment 24 hours a day. But there’s a reason why it’s called “The City of Broad Shoulders”. We work in Chicago. New York is where you go to play. But Chicago is the city that works. This is a haven for workaholics. And if you work in the corporate sphere, the reason you have that beautiful office with every window overlooking Lake Michigan is because it’s your home away from home. This is the place where you’re gonna spend most of your life, so you live well in it. You may keep your family in a beautiful house in the suburbs. But during the week, your business address is your real address.

Work isn’t just an occupational thing for us. In Chicago, work is a blood sport. It’s fun. If you are career minded, this is definitely the place for you. There is so much money in this town that it’s vulgar. But it’s not like New York. Money’s not the point, at all. Money is just a barometer that lets you know how you’re doing. You spend way too much time at work to actually get out and enjoy your money all that much. In Chicago, your name is your collateral. It’s all about reputation…becoming king of the hill. Being the best and being acknowledged as the best. It’s a very midwestern thing. And being from the Midwest myself, I made it my business as an independent contractor to work in every highrise I could, where every window had a spectacular view of the city on every job I worked, every day that I went to work. But having said that, don’t get the impression that work is all there is to being a Chicagoan. This is the biggest city in the Midwest, but it’s still the Midwest, as in the heart of the Bible Belt. Don’t let the skyscrapers fool you. This is the heartland, the middle of the country. 

Family values are everything here. Outside of Chicago, there’s nothing. Just farms and small towns, for hundreds of miles. People come from around the world to work here, but the natives all reflect the tough, Christian values of all those country folk in the rest of the Midwest. You work hard and you play hard. You provide well for your family. You buy homes in the right neighborhoods so your children get into the best schools. And one other thing: Churches are huge here, both literally and culturally. The churches and temples are packed, not just on the sabbath but all week long. There’s always something going on. Chicago choirs are extremely competitive. Gospel Grammys routinely go to Chicagoans. It‘s the weirdest thing, for a city this big, this sophisticated, and this cosmopolitan to have such a deep relationship with faith. But if you’re a midwesterner, it makes perfect sense. 

Chicago is New York the way New York would be if it was a city in the Midwest. New Yorkers generally despise Chicago and can’t wait to leave, and vice versa. It may resemble New York, but at its core, Chicago is the embodiment of the entirety of the Midwest: Work, faith, and family, in that order…our holy trinity. We’ve got plenty of atheists, but faith is just part of the fabric of the city. I’ve met real witches who belong to actual covens in Chicago. But even so, that’s still faith in a higher power, and they’re deeply devout. Irish Catholics come out of the woodwork every St. Patrick’s Day. There are enormous Hindu, Buddhist, and Muslim communities, and Judaism is a stable of Chicago. It’s an enormous city with room for everybody, so if you aren’t into religion, that’s cool. Just work hard, live and let live, and you’ll love it. In Chicago, being lazy is way more unforgivable than being an atheist. So if you’re seriously thinking of coming to Chicago, take these tours. See what you think. Chicago may be calling you. Yes, it’s meat locker cold in the winter. Our winters can be brutal. But that’s why we spend 98% of our free time playing outside in the summer. My summers in Chicago are the most fun I’ve ever had!