The Heartfelt Collective: CHICAGO TRIP REPORT - PART 4
From Chicago to Ann Arbour, our last full day of exploring.
Current Date:Tuesday, May 27th
Time: 1:05PM
Status Update: On my lunch break, starting this blog post.
Hello, hello, hello! This is the final Chicago blog post, documenting our last full day of being in America. We wandered around downtown Chicago again, just to see the sites one more time before we had to head to our next location. We drove about 4 hours to Ann Arbour Michigan where we had our hotel booked, and ended up eating in the restaurant there. It was also our two year anniversary this day, so we had a fancy dinner to celebrate!
We woke up pretty early on Sunday morning. I was pumped from the concert so immediately started writing my Cowboy Carter blog post. I wanted to try and capture all the thoughts and feelings I had swirling around my head, which was a lot so I’m sorry if that post was all over the place. Reg was still sound asleep so I had lots of time to type up some content. It is what started me getting back in to a creative flow with this blog!
When Reg woke up, we weren’t sure what we were going to do. I knew there was a breakfast spot I wanted to try and that was pretty much all we had on our itinerary for the morning.
Goddess and the Baker
165 W Superior St, Chicago, IL 60654, United States
This is another breakfast place I found thanks to the good people of TikTok and Instagram! It was very full inside, although the line wasn’t too long. One of the employees gave us a little menu so we could figure out what we wanted before we got to the cash. They had a lot of delicious pastries that it was hard to choose what to get. My eyes tunnelled visioned to the Cruffin (croissant muffin) and while it looked amazing, it looked like it could potentially be too much on top of a breakfast sandwich.
Did that stop me? No! I got it. I did get water to drink instead of a vanilla chai latte to try and keep the calories a little lower though! Feels healthier that way. I say as eat a colossal sized dessert filled with cream.


Downtown Chicago
After we were done our delicious breakfast, we had some time to kill before it was time to check out of our hotel. We didn’t want to leave too early because we needed to time it right with our next hotel check in time in Ann Arbour. We were both (or maybe it was just me) full from our breakfast so decided to wander around the streets of Chicago.
I love the Chicago skyline! I get the tall buildings of Manhattan effect but without the crowds and an added river in the middle of the city. Their water looks really nice as well, especially compared to the Seine in Paris. I said it before and I’ll say it again, it feels very The Dark Knight vibes! Kept thinking I’d see Batman pop out of the alleyways.
I also love the fact that their metro system is elevated in some points. All downtown I was able to look up and see the trains go by. That is more what I envisioned for technological advancements in the future, trains above the cities! Maybe it’s just me but using my imagination, it’s kind of giving flying train vibes. But you really have to stretch your mind for that.
The more I’m looking at the second picture, the more I’m appreciating the fact that you can see the buildings (I love tall buildings) but you are still able to see a majority of the sky as well. It’s just a really great city layout (I say that as someone who spent less than 72 hours there and only took Ubers or walked). In the words of Charli XCX, “Everything is romantic”.


The Bean, Round 2
We wandered around and eventually found ourselves back to the Bean! So we snapped a few photos there again, not knowing when we’d be back to see it! There was a couple who asked me to take their photo in front of it, and of course I did! I love taking photos of others, and they offered to take some of us too. They did a really great job! I think the Bean is such a cool sculpture to have in the city, because it’s reflecting the beauty of the city in everyone’s photos. No matter what angle you’re at, it’s capturing the magesticness (according to Google Chrome that’s not a word) of Chicago!





After that we wandered back to the hotel, walking under the train tracks and seeing all the half marathon runners walk by with their participation medals hanging around their neck. It felt like marathon weekends at Disney, but without the Mickey ears.
I was a little worried that traffic would be bad trying to leave Chicago since it was a Sunday and there had just been a big marathon. Traffic wasn’t that bad, it was trying to escape the underground highway of Chicago that was scary! I felt like the Joker was about to pop out of a transport truck and try to shoot me with a bazooka or something.
Siri did not understand that we were underground so she kept trying to direct us to roads that didn’t exist. When I’m telling you we ended up at a shipping dock for a building, I am not exaggerating! The screenshot from The Dark Knight could very well be the same area I got trapped in.
I was on the road headed straight and all of a sudden there was no where to go. It was just a loading dock. Luckily it was easy to turn around but at that point Siri had abandoned us, I just took a right turn and hoped for the best. Luckily it was the correct decision and we finally saw sunlight again. Had no idea where I was at that point but being above ground again would hopefully get Siri back on track and get us out of the underground tunnels!
We made it out and even crossing in to Indiana was not terrible. The lines were short and we breezed through the toll booths this time. We said hi to our favourite billboard lawyer and it was smooth sailing. Until it wasn’t. We were stuck in a traffic jam due to construction for about 45 minutes which wasn’t ideal but I managed to pass the time (singing out of key while Reg suffered in silence). Eventually we made it to Ann Arbor!
Weber’s Hotel
3050 Jackson Ave, Ann Arbor, MI 48103, United States
We finally made it to our last destination of the trip, Ann Arbor Michigan! While we were planning this trip, I didn’t really want to do another 12 hour travel day so I suggested we break up the drive on the way back. We looked at the map and I think my exact words were “I’ve heard of Ann Arbor before”, so we picked it as our stopping point. It was also our anniversary so I didn’t really want to be driving 12 hours for that reason as well.
The hotel itself is pretty eclectic, no coherent theme was established. The lobby felt like a lodge in the woods with a giant gold deer statue, the elevators were made of old wood and felt like something from NYC, the rooms were super modern and even had a bluetooth mirror. Yet somehow it all worked! I only took photos of the hotel room because I was very tired from driving all day.








We debated if we wanted to go explore the city, but I honestly just wanted to eat dinner at the hotel and be lazy for the rest of the evening. We accomplished both. The dinner at the hotel was really good. It was kind of busy due to the fact that it must have been graduation weekend or something, but only took about 20 minutes to get to our table.


The menu had a lot of options, but I had checked it out beforehand knowing I would be ordering the truffle mac and cheese. While it tasted amazing, it arrived in a trough sized dish which was too much for me to eat in one sitting. Reg on the other hand managed to eat his entire 16oz prime rib. Photo of his hand for comparison. Food was amazing and I wish I could have finished my meal!



We finished our night off by watching The Dark Knight since I had been talking about it all throughout our time in Chicago. Luckily American Netflix had it in their library, so we pressed play as soon as we were able to connect the laptop to the hotel TV. What a great way to end our day!
Final Thoughts
This concludes our blog posts for this road trip! It was a whirlwind trip, but it was so much fun. I am so glad I got to see Zack for the first time in years, and see Beyoncé for the first time ever. I am grateful that I have an amazing boyfriend who comes on these adventures with me, and doesn’t complain when I’m singing the Wicked soundtrack for the fourth time that day. I am thankful to have my own car that can take us back and forth on these trips with no issues. I am happy that the city of Chicago was amazing and made me want to go back eventually. Maybe if Beyoncé doesn’t come to Canada again for Act III, however I may fly instead. Driving was fine but took a lot of energy out of me.
Thank you for taking the time to read my blog! I have so much fun recapping my trips and editing photos to go along to enhance the story. Our next major trip isn’t until this fall, but I am so excited to blog about that. We are also going to Toronto in September to see Lady Gaga, so maybe there will be some posts about that as well.
I’m still trying to figure out the direction of my blog but for now I am just trying to have fun with it.
Thank you for reading,
Shannon