As we were approaching our fifth wedding anniversary, I knew I wanted to do something special with my wife.

I started doing some research and based on the amount of time we were able to be off of work, I decided to go to Chicago.

Since both of us work in public education, the beginning of the school year is a hard time to be away, we should have considered that when we got married in October! Although we could have easily driven to Chicago, I am not a fan of driving in big cities. Airfare is just crazy these days (and back in those days), so I decided it might be fun to take the train.

We worked a full day (big mistake) and then drove two hours to get to Kalamazoo, MI where the train station was.

The station in Kalamazoo is in a part of town that might be nice during the day, but it didn't seem as nice in the evening. There were also many interesting characters hanging around the station. My wife and I were a little concerned about what I might have gotten us into.

We made it onto the train though and surprisingly, the trip was rather enjoyable. Though not anywhere near as fast as a plane, there was much more room to spread your legs on the train and if I remember correctly there were only a handful of people in our car.

Truthfully, if we had driven, I probably could have gotten us to Chicago faster than it took to: drive to Kalamazoo, wait for our train, and then travel by train into the city. It was extremely less stressful just being dropped off in the heart of the city at Union Station though.

We got a cab from the station and had them take us to our hotel. I did one of those name your price things where you don't get to pick your hotel. You simply say the area you want to be in, the "star level" you want your hotel to be and how much you are willing to pay and they match you up.

We ended up at a very nice place called Hotel Sax. If you look for it though, you won't find it. It has since been purchased by Marriott and is now called Hotel Chicago Downtown.

When we arrived at the hotel we immediately wondered if we were out of our league. There was a pretty trendy night club in the hotel so there were several large men working as bouncers at the main entrance. Likewise there were many men and women dressed up much finer than my wife and I in our travel clothes.

The staff was super friendly though and didn't seem to mind that we were obviously not from around there. We got up to our room and it was nice. It really wasn't anything special, but it wasn't dirty and the furnishings were nice, so we couldn't really complain.

This is a view from our hotel window, the rooftop at the bottom of the picture is from the House of Blues.

It was close to Midnight by the time we got to our hotel, but we still thought it might be nice to go out for a little bit. Having never been to Chicago myself, I had no clue where to go. We didn't want to venture too far and ended up around the corner at 10Pin

To get to 10 Pin Chicago you have to enter a building and then go upstairs. Once inside you find yourself in a bowling alley in the heart of the city. We soon found though it wasn't like the typical bowling alley you find around our hometown. Everyone was very dressed up and the drinks were very expensive. We were good sports though and had one drink then we decided to call it a night.

The next morning we got up and walked down to State and Lake to get some breakfast. I remember my wife got something like an eggs Benedict with turkey sausage, but I don't remember what I got. It looks like they have changed their menu since we visited.

After breakfast we got a cab over to the Shedd Aquarium. I had purchased tickets ahead of time and I was really looking forward to visiting. It absolutely did not disappoint, and we got to see so many awesome displays and animals. Although I didn't get any pictures the tropical fish section is my favorite and I could just sit in the dark for hours watching them swim about here and there.

The penguins were pretty awesome too. Shedd is a definite must visit if you find yourself in Chicago. It gets busy though, so make sure you get your tickets ahead of time.

We took a cab back to the hotel and decided to walk over to Portillo's for a late lunch. It ended up being quite a bit farther away from our hotel than we had realized, but we made it alright. Portillo's is an iconic Chicago eatery and is just as famous as the many deep dish pizza places scattered throughout the city.

I couldn't go to Portillo's without trying the classic Italian Beef Sandwich and my wife got the chopped salad. It is pretty crazy inside of Portillo's, so it is easy to get overwhelmed when you first walk in. The best way I can describe it is a mall food court with much less seating space and much longer lines. My wife and I quickly split off to go to our separate lines to get the item we wanted and began the long wait to even put our order in.

We finally got our food and tried to find a place to sit. A table eventually opened up and we quickly swooped in to claim it. As I mentioned before, seating is tight. The tables practically have you sitting on top of the people next to you, but Chicago is supposed to be the friendlier NYC right, so no big deal :)

The food was great and even though it can be quite the experience, I recommend visiting at least once in your life.

We made the long walk back to our hotel and decided to try to take a nap for the rest of the afternoon/evening.

Stay tuned for the continuing adventures...

All pictures were taken by me.

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