The Windy City

Our Chicago vacation was so much fun! Looking back on the pictures makes me so happy. Reminiscing of the days that I was able to spend hours and hours with my favorite person. I really can’t wait for our next week off together.


We slept in again Monday morning enjoying our slumber and soaking in the feeling of vacation. We had a mid-morning architecture boat tour planned and grabbed some breakfast on our way to the boat.


With coffee in hand we arrived for our boat tour to find out that we were an hour late 😉 Oh vacation you mess with my head. Thankfully, they were kind enough to reschedule us for the next hour tour and we ventured up and down the river until it arrived.

It was a gorgeous day in the city and the tour was the perfect way to spend it. As the tour guide stood up with the microphone she announced that the next two hours would be loaded with more information and history about Chicago then you’d ever known before. I quietly heard Rob say “Yes!” under his breath in appreciation. My history lover was in heaven.

The tour was extremely detailed and so much fun to see angles of the city that you couldn’t without being on the water. Our ride up and down the river channels was jam packed with information on when buildings were built, who built them, and what they were originally used for. We learned all about the Chicago fire, The Worlds Fair, and everything else in between. It was a beautifully relaxing time spent outside on the water. We were so glad that we chose to book the tour. Definitely a recommend.


After our tour we headed towards Millennium Park once again to meet up with one of Rob’s family members who lives just outside of the city. He was kind enough to make the drive in to see us for the afternoon. We ate at Brown Bag Seafood Co just off the perimeter of the park and enjoyed every bite of our lunch and minute of our company.


We ventured through the park across the street with Doug once we finished up our meals. The weather was so beautiful, we couldn’t have asked for it to be better and we wanted to soak in every minute.


We ended up walking all of the way to The Buckingham Fountain, since it was one land mark we hadn’t ventured down to yet. It was gorgeous, complete with a rainbow in the background. From that location in the park we were able to see the aquarium, planetarium and The Field Museum sitting right on Lake Michigan.


We said our goodbye’s and decided to start making the trek back to our cozy apartment. It had been a long day of walking and our feet were ready for a rest. We had a location we were going to walk to and then Uber back the rest of the way, but that didn’t seem to fit into the plans and we ended up walking the entire way back. My feet were done!



On the way, we did get a little pick me up from Eataly full of gelato, cappuccino, and chocolates. I was living through my parents who were in Italy at that time and sending me amazing pictures of the gelato and coffees that they were having. 😉



After our rest back at the apartment we got dolled up once again and headed to The Second City comedy club for our comedy show that night. This was one thing we really wanted to do when talking about visiting Chicago. It was so much fun and we are so glad that we were able to make it.



Rob even got on stage during our comedy show. “The Whitest Male in the Room” was the contest that they were going for. After this picture was taken, they asked for those to sit down if they hadn’t ever Google boat prices. You can bet that my man HAS done that, so he was the last of two guys on stage. So proud 🙂


Tuesday was our last day in the city. Thankfully we had a full day to venture around and enjoy the city before our flight left in the late afternoon. Since Chicago has some of the best shopping, we decided that buying our winter coats for the season sounded like a fun idea. So we shopped until we dropped and came out ahead with two coats to keep these Floridians warm for their first winter. Now that we bought them I am sure it won’t even get cold here.

Off we went back home that night with a quick direct flight into Raleigh. Unfortunately, it was late once we got back home since we had another hour drive back home from the airport. My handsome Mr. offered to drive us back since he was still on vacation for the rest of the week and this girl had to wake up for work bright and early the next morning. What a saint 🙂

Vacation with my best friend was a blast. I am so glad that we were able to enjoy every minute of it, relax, see new things and have new adventures together. He is simply the best.

ANNDDDD if Chicago had that weather through all of the fall and winter that we were able to experience, I would live there in heartbeat.


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