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Chicago is like a huge jigsaw puzzle that is comprised of hundreds of otherwise-mismatched pieces that somehow come together to form something unique and wonderful. I have been going to Chicago for years, and recently I started taking an extra day there whenever I was there for work. I did so in order to be able to explore one more neighborhood in this tapestry of a city each time I happened to be in town. It had been fun and rewarding so far, and when I recently found out that I'd be going back to Chicago for meetings, I did the same thing and booked my return flight 24 hours after I knew I'd be done working. I wasn't worried about lodging, either, as I always travel with HotelTonight, an app that helps people find last-minute accommodations. I was sure I'd find an Old Town Chicago hotel when that need arose. It was almost time to explore a new part of town.

The Name

In truth, Old Town Chicago is a neighborhood that's about the same age as the communities that surround it. The residents of this neighborhood named it Old Town, at least unofficially, after World War II. During the war, the residents banded together to form a neighborhood defense unit, and this unit patrolled the area regularly to watch for suspicious activity. After the war was over, the unit began to sponsor an annual event called the "Old Town Holiday" and the name stuck since that time. Before it became known as Old Town, the area was known as North Town.

The Comedy

I'm not usually one for visiting landmarks. If I happen to see them as I explore a new place, then great, but I don't generally go out of my way for them. I like to get a real feel for what it's like to live in a place. When it comes to Old Town Chicago, one landmark speaks to the community directly. That landmark is the Second City improvisational theater, which is known around the world for producing legendary comics for generations. It's been here for more than 50 years, and the list of people who have passed through this place is stunning. Dan Aykroyd, John Belushi, John Candy and Chris Farley are just a few of the names anyone would recognize who have performed here.

The Local Shopping

I'm not generally much of a shopper, either, as I've always felt that you can go to a mall in just about any city. That said, the shopping in Old Town was actually quite fun. There are very few chain stores here, and instead the streets are dotted with local shops and boutiques. I wandered around in these places for a couple of hours and even bought a few things, which is relatively rare for me. I really enjoyed myself.

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I had done a lot of walking that day and I was tired. It was time for a rest, so I pulled out my phone, opened HotelTonight and found an Old Town Chicago hotel just up the road. I booked it and began to head in for what I hoped would be a long night of sleep after an enjoyable day.