Around the time January and I got married, I was doing a lot of freelance work for various Chicago-based companies as a result, I found myself doing a fair bit of travel there for work-related meetings. Given that I lived on the north side of the city for several years, I would regularly take trips out there each year to meet up with friends as well. After one of these recurring trips, I remember coming home to hear January relay the story of her dad asking her if she was concerned about how much I was traveling, and wondering if she thought it was possible that I was "seeing someone," and travelling so much to see a "mistress."

Last weekend, I took another trip up to see my mistress Chicago with Jay and Jason. What instigated the trip was the fact that Jay's wife Jen was planning to have a "girls weekend" at their house and, being the wise man that he is, he decided to take the opportunity to get out of the house for a while. We didn't have any plans in particular, and just loaded into the car on Thursday after work and hit the road.

Hitting the road. Kudos to Jason for his awesome photography.

While most of my trips to Chicago have involved crashing on various friends' couches, we got a pretty good hook-up this trip out; Jay was able to get us booked at the W hotel downtown -- a super-swanky, upscale hotel -- with an employee discount. It was great being able to set up camp in the heart of the city, just a short train ride away from almost everything we wanted to do. The sleeping arrangements were a bit tricky, though; This room had one king sized bed and a short chaise longue. It wasn't the most comfortable thing in the world, but we each took one night on it, using the faux-fux bed runner as a blanket.

January calls this my "dead man's pose." Thanks, Jason, for showing me what I look like when I sleep.

I mean, this hotel was upscale. Walking into the lobby at night was like walking into the scene of a movie where the ultrahip glitterati meet on a Saturday evening to schmooze. Here's a little footage from the lobby to give you a pretty accurate feel for the place.

Our plans were pretty ambitious: hit as many of the obligatory Chicago restaurants as possible, attending to the Pitchfork Music Festival on Saturday evening, and try to settle the age old debate: Lou Malnati's versus Giordano's. In the time between, we spent a lot of time walking around the city and visiting with old friends.

We were actually able to visit several parts of the city that I rarely, if ever, got a chance to see while living there. Chicago actually has several beaches along Lake Michigan, and we spent a little time there Saturday evening before going to the music festival. Jason was able to capture this video clip, which struck us all as hilarious, although were weren't entirely sure why.

While we were never able to settle the pizza debate -- primarily because we ran out of meals -- we did have a nice, laid back time in one of my favorite cities. Personally, I'm hoping Jen volunteers to host her girl's weekend next year as well.