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I love both Chicago and Tampa very much. There really isn't a right or wrong, it just depends on what you want. Chicago's much larger and has a climate closer to Toronto's. Has everything a world class city offers and is still relatively affordable. Tampa is less expensive. Given that you will be making $50k no matter which you choose, you'll get more bang for your buck in Tampa. Tampa has a tropical climate. Great beaches and there's a good bit to do. Orlando is only about 85 miles away, so you have access to all of its offerings as well, especially if you choose a northeast suburb of Tampa Bay. I lived in Orlando for a year about 10 years ago and fell in love with the whole Orlando/Tampa Bay corridor along I-4. The Tampa Bay area is a retirement oriented area, but there are enough young people to allow you to find peers to socialize with. It just depends on what you want. Personally for me, I would choose Tampa because it its climate, lower cost of living, all of the recreational assets, and the year round outdoor activities. No matter which you choose, it will be a good area. Good luck!
Thank you so much, and considering I will be able to work remote I can get away with moving anywhere in in the state, so I won't be stuck in Tampa so to speak and can move around the state. That being said, Chicago is still very attractive to me so it's gonna be a tough decision.
4 seasons, better skyline, better architecture, more urban, walkability, more sophisticated. So many reasons.
Tampa is boring and too hot for much of the year, besides it is in Florida which is full of nuts.
It depends. The four seasons would actually be a drawback if the OP is looking for benign, equable climates. And since OP mentioned the salaries in the scenario to be the same, there would be better bang for the buck in Tampa compared to Chicago.
Better skyline? Not really. Do you mean skyscrapers? Why would skyscrapers make you move to one place over another? Lol
Chicago over Tampa, any day, every day.
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