My brother Shawn, nephew Branden and I took a trip to Chicago over a weekend. For all my travels, I actually had never been to Chicago city proper (just the outskirts). We saw all the sites, like Grant Park, Downtown, Hyde Park, and the beaches of North Shore. I found the city to be a really clean and well designed place with amazing parks, a world class zoo and top notch subway and public transportation options. The food, for me, was a consistent "miss". Nothing really stood out to me or prompted me to want to go back to try anything in particular. That part may have just been bad luck.

I enjoyed our strolls through various far flung neighborhoods in Chicago and down Michigan Ave. I really think the city has a great flair for beauty and it's a multi faceted place. Great beaches, great culture, and lots of things to do. I did not really connect with the city to any degree and I wouldn't go out of my way to return but I would certainly not have any issue with going back if ever the need arose.