Chicago Trip: Day One

Chris and I decided earlier this year that we would make a list of places we wanted to travel to and slowly begin to cross them off. Our first adventure led us to Chicago this past weekend! Flights were cheap and we got a killer deal at the Palmer House Hilton.

For weeks we were counting down the days until our mini vacation, putting together a spreadsheet of suggested restaurants, bars, sites and activities. Chris even created a compiled map of everything on our spreadsheet which ended up being really helpful since we wanted to play our plans mostly by ear each day. I’ve never planned a trip with anyone as organized as we had things. I was seriously impressed with ourselves and thought to myself, I could definitely keep him as a travel companion for the future! 🙂


March 1 finally arrived and we caught an early morning flight and took the train into the city to check into our hotel. The Palmer House was only 2 blocks from Millennium Park so naturally, Cloud Gate (or the bean, as I like to call it) was our first stop. We took pictures and walked around the park a little until we decided we were hungry. We found a place on the way back to the hotel to grab a bite, called Rudy’s Bar and Grill. The food was surprisingly good for a bar. My salad came with this amazing pretzel roll that I was left craving for the rest of the weekend! It was just the perfect amount of firm on the outside and soft and salty on the inside.. I have to find a recipe!! Pinterest

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After eating I was feeling tired since we had been out late at the Houston rodeo the night before and I had been too excited to get much sleep before our flight. So, we headed back to the hotel for a nap.

We had originally planned on trying to eat dinner at a place called Ruxbin, which had been written up as being one of the top foodie places to visit in Chicago. Well, halfway to the train Chris asks me if I have our tickets to the show we were seeing later that evening. Of course, I didn’t! 😦 Walking back to get the tickets set us back on our schedule and we didn’t have time for Ruxbin because they don’t take reservations and it was a bit out of the way from the theater.

I could tell Chris was a bit upset but I told him not to worry and that we’d find somewhere else for dinner and we’d try again tomorrow. We came up to street level from the subway stop and saw a restaurant called Devon that looked pretty promising with lots of people, dim lighting and a swanky/modern kind of feel. We decided to give it a try and we were glad we did. We happened to catch happy hour and ordered some specialty martinis and several appetizers to share. It was all pretty tasty, especially the lobster mac and cheese!


After dinner we headed to the theater to catch I Love Lucy Broadway. I was seriously SO excited about this because I grew up on Nick at Nite and constantly watched her show. At one point I even had my room decorated in I Love Lucy stuff. The play was set up as though we were a live studio audience and they were filming two episodes. They even acted out commercials from popular products of the time period and the host interacted a lot with the crowd. I would highly recommend it to anyone that loves this classic; the actors were true to character and there were lots of funny scenes.

When the show was over we found that one of the bars that was on our list was nearby so we strolled the streets until we came to the Clark Street Ale House. The place was totally up our alley. It was sort of divey and you could tell that most of the customers were locals. It had a neighborhood bar kind of feel with a very relaxed atmosphere. Their craft beer menu was impressive which was exciting for my beer aficionado. We ordered a round and sat around recapping our day and discussing our plan for the following day.


We headed to bed afterward in preparation for a full day of sight seeing and romping around the city.

My friend Chelsea recently blogged about her trip to Seattle and I liked how at the end of each entry she included what she learned that day about the city, so I am going to do the same. (Thanks, Chels!)

  • People in Chicago are just as nice, friendly and helpful as people in Texas.
  • Ear muffs or a hat/hood and gloves are essentials for the cold and wind you experience while walking the streets.
  • Pack comfortable shoes, your feet and legs will be sore regardless.
  • It’s probably best to refer to the Willis Tower as the Sears Tower still, as some people seem to be bitter about the renaming.
  • Public transportation in Chicago is pretty efficient and reliable.

Stay tuned for Day Two!