Just after Christmas in 2012 Jeb and I head out to Chicago for a vacation together and to celebrate New Year’s. I have been to Chicago several times before because I have family in Illinois. But this was Jeb’s first time there.

The “bean” was our first top on our trip. I think this thing is so neat looking! It’s funny to me that this has become such an iconic symbol of Chicago, considering it hasn’t been there for all that long.

Really trippy looking haha.

Jeb pushing it lol.

This trip was definitely a chance for us to wear lot of different fancy coats haha. As can be expected it was pretty cold while we were there! I kept trying to look cute and sacrificing warmth in the process lol.

Reflection of the city in it. We kind of ate our way through this trip lol, but I didn’t really take pictures of that aspect of our trip. I took Jeb to Giordano’s and made a fan out of him! I know some people disagree but that’s my favorite deep dish pizza place, so delicious! We also went to Portillo’s which I really love.

Chicago to me is the perfect “Christmas city”. I’m not sure if it is just because it is so cold, or because there are so many pretty Christmas trees there, but it definitely feels like Christmas in Chicago.

We also went out to navy pier and took some pictures.

We didn’t taxi a single time on the trip. Not everything is super close together in Chicago, so we definitely did a lot of walking. We had to, in order to balance out just how much we ate! haha.

Why do people always take pictures of us where they stand so far away from us and make us look tiny in the picture? lol.

Since I wanted to go up in both the John Hancock building and Sears (Willis…) tower, we decided to do one at night and the other during the day. So these pictures were taken from the top of the John Hancock building at night.

Looking out over the water.

Another really pretty Christmas tree!

For New Year’s Eve we bought tickets to go to the ball at Navy Pier. It was a fancy affair and we were excited to get dressed up! Thanks to a last minute fiasco with Jeb’s tux rental being screwed up- he ended up buying a used tux to wear to the ball.

The ball was pretty awesome. There was live music in one area and a DJ in another. Our tickets included food (small snacks) and an open premium bar! Plus there was a champaign toast at midnight and fireworks outside over the water!

Finally a picture of us actually together! Looking pretty snazzy if I do say so myself!

We took this just after midnight. First picture of 2013! You can see the fireworks going off in the background behind us. We pretty much just watched the fireworks from inside because it was below 0 degrees outside!

The next day (our last day) we went up in Sears Tower. We had to get some classic, iconic pictures of Chicago from above.

The tall black building in the picture below is the Hancock building.

I don’t know why, but this thing really freaks me out! It does not feel secure or safe at all standing on just glass hundreds of feet above the city…

Sitting down felt even less secure- because if it started to fall you couldn’t just quickly and easily dart back inside! This made me feel nauseous sitting here long enough for a picture. But worth it to have!

We then got on the train and headed back home. That was another unique aspect of the trip- taking an overnight train ride together. It was fun being able to show Jeb Chicago and to have so much good food there together!

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