The Queen’s Chronicles – Chicago

It has been a bit since I headed off on a mother daughter weekend with my oldest but she loves to plan a getaway and, well, I love to get AWAY so we decided to take the long Memorial Day weekend and head to Chicago. Neither of us have ever been and it looked like a city we could explore in a short visit. The bonus for me was she planned the entire itinerary and I pretty much just followed her around like a lost puppy. I’m wrapping up our trip and sharing all that we did on our visit in todays Queen’s Chronicles.

After we decided on Chicago, it seemed like the first thing we heard from people was a warning about how much crime there is and to be careful. Here is the thing, everywhere we go can hold some danger if you are not aware and cautious. Our experience was really no different than any other city I’ve visited including Austin, Houston and San Antonio right here in Texas. We made sure to be aware of our surroundings, didn’t stay out late at night and researched the areas we were visiting and never once felt unsafe. We found Chicago to be full of good food, friendly people and beautiful architecture so follow along and see exactly how we spent our long weekend in Chicago!

In order to maximize our time and our Southwest miles, we flew from Austin to Midway on our way to Chicago and took the flight back to Austin from O’Hare. Upon arriving we were so proud as we navigated the “L” train from Midway to the downtown stop just around the corner from our hotel.

First things first, we headed to Giordanos for a deep dish pizza. The Chicago deep dish is so much different than pan pizza in Texas that’s for sure. It is definitely more like a pie with fresh ingredients in the filling. You can actually ship this pizza and I’m thinking Keith might receive this for Father’s day.

Next up was the Sky Deck at Willis Tower (formerly known as the Sears Tower). Jordan reserved our time slot ahead of time online and it was a super quick entry. I am sometimes afraid of heights and wasn’t sure how I was going to feel about walking out onto the glass deck but it did not bother me in the least. Maybe because you stand in line and then have only 90 seconds to take some pictures before they rush you along. You can go through the line as many times as you would like, however, so we did take two trips through. My first view of the city was from the top and it was so good! I loved that we were seeing the sun begin to set while we were there and the lighting was perfect for a new favorite pic with my girl.

We headed out on day two and stopped for a coffee at Goddess and the Baker. There are several througout the city and the pastries looked incredible! We had brunch reservations later that morning and decided to save our calories but I may have regretted this multiple times as we never made our way back as we hoped to.

Next up we spent some time walking around Millenium Park and doing touristy things like pictures at the bean. Lots of beautiful flowers and other art installations here so it is a great place to soak up the day and stretch your legs.

We headed to Terrace 16 for our brunch reservation with more beautiful views of the city along the river. London House is another restaurant with great views literally across the way but Jordan read that Terrace 16 was a great option that was a little easier to book. The food was good and the mimosas were bottomless so we didn’t have any complaints.

Imagine my surprise as we were waiting for our architecture boat tour when I saw Andrea from Living on Cloud Nine walk by!! Truth be told, I noticed her sweet pup Stella first and then I’m sure we caused quite the scene hollering as we were both equally as shocked to see each other in such a sea of people. It has been a few years since we have seen each other in person so it was good to hug her neck.

Next up on our adventure was the Architecture boat tour. Almost everyone who gave us suggestions for our trip indicated this is a must do and I would agree. The history and stories behind why designs were chosen for some of the buildings was fascinating. Hearing how some of the buildings have evolved from their originial use to a new function today was also interesting. There are several tours available but we chose the one through the 90 minute Chicago architecture center and the tour guide was both knowledgeable and engaging.

We dined at a little meditteranean restaurant along the river. Beatnik on the River is breezy and casual with a whimsical feel. The food was yummy too but I am fairly certain after all our walking I never even considered taking a photo and dove right in!

We started off day 3 with brunch at 3 Arts Club Cafe which is located inside the Restoration Hardware in the famed Gold Coast neighborhood. Such a timeless space originally home to the 3 Arts Club, a residence built in 1914 for young women studying music, drama and the visual arts. I love a lovely latte and the food was delicious. I was definitely happy to have this amazing sourdough in my belly to sustain all the walking the rest of the day!

We walked off our lunch and mosied through the streets down to the park and eventually lake Michigan which is the perfect shade of blue. The Shore Club was the perfect little stop to sip a cocktail along the water. I chose the Chicago 71 which was a drink giving a little tribute to the Chicago fire. Hard to tell in the picture but my champagne was extra bubbly and smoking!

We hopped an uber and headed to Wrigley field for a little baseball. I feel like this is an iconic place to visit and originally it was not on our itinerary but so many people told us we had to go. Taking a tour of the ballpark propbably would have been a better choice for us where we could of learned the history, etc but this was a last minute add so the game was our only option. We have just been to alot of ballparks and watched a lot of baseball so we were a little underwhelmed with our visit.

We rode the “L” train back to downtown which was much faster and cheaper than taking an uber and headed for the next stop on our list, Portillos. I had to steal the pictures from the website because this sandwich is incredible but also very messy and not very pretty in real life! We chose the italian beef with both sweet and spicy peppers “dipped”. The entire sandwich is made and then dipped in the juices…y’all…so yummy! Riley’s friend from college who grew up in the area also told me their chopped salad was amazing but I could not resist trying this sandwich.

We walked off the sandwich and headed to Navy Pier. There are tons of restaurants, carnival like rides, a little shopping and we stumbled upon some live music. I was apparently just soaking it all in because I took zero pictures! We ended our day at the Offshore Rooftop and had the best time sitting at the bar enjoying the views and visiting with some new friends we met from Arizona and Miami.

On our last morning we headed to Wildberry Pancakes and I just have to say, I’m glad we saved this for last or I might have wanted to eat here every day!! Just across from Millenium park sits this little cafe with the most amazing breakfast. I had the Napa omelet out of curiousity as it included havarti cheese, applewood smoked bacon and figs. It was so good! We added on the signature berry pancakes and I’m still dreaming about them. That is whipped mascarpone cheese on top…holy yum.

We walked off our breakfast by headingi through millenium park for a few more touristy pics at the Bean and then on to the fountain at Grant park before heading back to our hotel to pack up our things.

Our last stop before heading to the airport was visiting the Palmer House Hilton hotel. Two friends told me it was a must see stop so we popped in and it is stunning. The hotel is over 150 years old and was built as a wedding gift if you can imagine! Many of the beautiful rooms do not have the lights on but we were able to find a kind staff member who gave us a peep at a few of the ballrooms.

Such a fun trip with my girl! Chicago surprised me. I’m not sure what I really expected but was pleasantly surprised with how lovely it is and how much I enjoyed being a city girl for a few days. While I loved not having to actually do the planning, I do wish I had at least peeped the itinerary and looked up the history of a few of the places we visited to learn a little about them. The Beatnik restaurant, for instance, had so much information online about the inspiration for the restaurant and history of the building. Definitely a lesson to keep tucked in my pocket for the future.

The next trip we have planned is to NYC for Thanksgiving as Carly Jo will be heading to dance in the Macys Parade with her senior drill team members! I haven’t been to NYC in almost 10 years and cannot wait to be back.

Share your 2023 travel plans! I love to hear where everyone is heading.