Chicago: "The Allergy City" (inside joke)
- Lauren
- Sep 12, 2022
- 7 min read

We arrived to Chicago late on Friday night. As you can imagine, it’s not the cheapest city to visit. While we would have preferred to stay downtown in the heart of the city, we had a private room in an Airbnb in ‘Uptown.'
The whole ‘private room’ set up was quite interesting. We were basically living in someone else’s house – entering from the same door, sharing a kitchen, etc. In our private bathroom, the whole side of one wall (which was shared with the host’s bedroom) was covered with a mirror, and Brad was CONVINCED it was a two-way mirror. Lol.
We were lucky to have free street parking in our very cute neighborhood, and the car stayed put the whole trip! I come from a no-stoplight-town (Louisville feels HUGE to me), so I was so unbelievably grateful to have Brad with me – who has traveled all over the world. He did some research and decided that weeklong bus passes would be our best plan of action. I am sure his Apple watch has the data, but I bet we walked 30+ miles in 4.5 days.
Saturday morning, we woke up and walked about a mile to brunch at a cute little place called “Pick Me Up Café.” The portions were HUGE – we easily could have (and should have) split a meal. I got Florentine Benedict, but I LOVED Brad's berry pancakes.

After brunch, we walked back to our room and then took a train downtown to the AVP tournament on the lake. We watched volleyball (in gross, sticky heat) for a few hours and then took the train back to our room. Brad kept having me repeat “Wilson is our stop” in case we were to get separated – because he knows I am not city-savvy and would be lost, quite literally, without him.

We changed clothes and hopped back on the train to Wrigley Field – where the Lumineers were playing a sold-out concert. The concert, for me, was truly a magical experience. There is something so spiritual about singing lyrics with 40,000 other people, under the city sky. I only cried four times! I stole a few pictures from The Lumineers' Facebook page to try to capture how the concert felt "larger-than-life." The last one is from our actual seats.
The “L” (as the natives call the train) was obviously packed after the concert, so Brad and I decided to walk the mile and a half back to our room. We stopped at a gas station along the way and got a shit ton of snacks. I told the cashier, “The worst part is, we aren’t even high.”
The next morning, we had to wake up early to get to the AVP tournament because the stadium is general admission and fills up very quickly on Championship Sunday. Once you get a seat, that’s where you stay the entire day, or else you’ll lose it. The weather was entirely different than the day before – wet, cold (still gross, but in a different way). My two FAVORITE teams happened to make the finals and would play against each other. You should have seen the look on Brad’s face when I said, “We should go back to the room.” I had to reiterate a few times that I TRULY wanted to leave before Brad was convinced.
I was cold. My butt hurt. My legs were sore. I was hungry. We were surrounded by hundreds of people, and I don’t like crowds. I knew I would find more joy watching the match back in our room, by ourselves, with dry clothes and a warm bed. With snacks. As I predicted, we had a lovely time watching the championship match on my laptop. Go, TKN!
Sunday evening was supposed to be our “fancy dinner,” but Brad and I miscommunicated about the reservations, and it turned out that we didn’t have one at the restaurant I selected for my birthday dinner. He took a nap, and I spent nearly two hours looking for a nice place to eat (I had something very specific in mind), but I kept striking out. After expanding my geographic search a bit, I knew I found the spot for us – Angelina’s Ristorante. The only bad part was … you had to call to make reservations. I do NOT like talking on the phone, so Brad offered to do it, and our reservation was booked for 8:00!
I think Brad and I would both agree that this restaurant – CLEARLY a hidden gem – was one of the highlights of the entire trip. We happened (sheer luck) to get the best seat in the tiny, quaint restaurant – on a platform, right next to the window, looking out to the patio and the Chicago streets. The table came with fresh bread and olive oil. I got a blackberry martini, and Brad got an apple cider old fashioned. For our meal, I got fusilli pollo, and Brad got veal marsala … both were INCREDIBLE (the pictures do not do it justice). Brad said, “I never want to eat anything else as long as I live.” We shared house made tiramisu for dessert (which means I just took a bite, because I don't really care for desserts).
I am SO glad we screwed up our reservation and ended up here.
We went back to the room, and I think I made Brad’s life when he came back from the bathroom, and I was watching King of the Hill – a show he recently introduced me to, that I LOVE.
The next morning, we had reservations for an architectural tour! I am not super “into” architecture or history, but I booked the tour for Brad, as he was a trooper and sat through endless volleyball matches with me. I. LOVED. THE. TOUR. It was beyond fascinating to me, and I was so impressed with our guide, Kylie. She was unbelievably knowledgeable but presented the information in a very digestible manner. I learned a lot and was in awe of the beautiful buildings. To me, "The Palmer House" was aesthetically the most beautiful, but Brad and I both loved our stop at "The Marquette Building" the most. Here, we learned about the Great Chicago Fire and how the city rebuilt itself.
After the tour, we grabbed lunch on the riverfront, and then Brad wanted to go to the Apple Store and then to Ghirardelli for a “hot chocolate,” which is really just melted chocolate squares.

We did some shopping, and then Brad said he wanted to take me to one more place, but he wouldn’t tell me where. We ended up at Lush (I had never been!), and he said, “I know we are in a rush to get back to the room, but I am not leaving this store until you pick out three items. (If you know me, I am very financially conservative, and I do not like spending money or having others spend money on me). I painstakingly (and excitedly) picked out my three items, but apparently, Brad had changed his mind and said I needed to pick out two more, so I did. Actually, I think Brad picked out the “ghost in the dark” soap and put it in our bag. Brad got me A LOT more for my birthday, but I don’t even want to mention it in the blog, because I am honestly embarrassed just thinking about how much he must have spent. I was (and am) severely spoiled.

We then went back to the room for Brad’s FAVORITE activity … watching The Bachelorette! 😉 Brad and I are third and fourth place, respectively, in our ‘fantasy Bachelorette’ league. #PowerCoupleStatus
The next day, it was my birthday! Gino’s East – a famous deep dish pizza joint – was on the itinerary. Brad and I smartly split an appetizer and a pizza, and we still had a TON of food leftover.

We went to H&M to get Brad a jacket to wear to the Cubs game later that evening, because both of us failed to pack anything long-sleeved, and the forecast changed on us (I ended up being the one to wear the jacket he bought for himself. Oops.) Brad poked fun at me, because I packed more of his clothes in my suitcase than my own – so this was on-brand for me.
I told Brad I wanted to go back to Lush to get my best friend Brooke a birthday present. We weren’t in the store for more than two minutes before I dropped a huge tub of the sample orange body scrub ALL OVER THE FLOOR. I was mortified and on the verge of tears, but the staff assured me it happens ALL the time and cleaned it up speedy quick. As we were checking out, I apologized again, and the associate said, “As some comic relief, we bottled some up for you!” Shout out to Gabby and Tucker for being so kind to me. Later that night, we went to a Cubs game, and they pulled off a W. Wrigley Field was electric, and the night was beautiful. We took the train home and watched another episode of The Bachelorette, which we had recorded.

Funny story – Brad claimed he was “listening, but with his eyes closed,” but he kept snoring. I exclaimed, “You aren’t even awake!” And he replied, “Yes, I am! This, this and this just happened.” Somehow, he was SNORING but still retaining information. We BOTH ended up falling asleep during the episode.
The next morning, we slept in quite late (for the first time the entire trip), but it was time to check out. While we packed, we watched the remainder of The Bachelorette, and I was very pleased when Brad asked, “Will you please pause it while I take a shower?” BAHAHA, so he IS invested!
I asked Brad if he wanted to put our stuff in the car and then walk to “Lucy’s” for lunch before we hit the road. Lucy’s was a fried chicken diner right by the train station that we passed more than a dozen times, but we never had time to stop. We, smartly (again), shared a bacon jam fried chicken sandwich and porky fries – neither of which we could finish. The food was delicious, the place was adorable, and the music playlist was fire.
One of my favorite moments actually happened on the car ride home. Brad, on his phone, was watching the ceremonious reveal of the Obama portraits at the White House, and former President Obama and First Lady Michelle gave remarks. Brad and I were both so moved by their speeches, we just looked at each other, with tears running down our cheeks. Brad will disagree, but I often fear we don’t share “enough in common” – and this was such an emotional bonding moment for me. We both laughed out loud when President Obama joked that the portrait artist convinced him "not to wear a tan suit" and when he called Michelle "fineee." ;)
It was a fabulous, whirlwind of a trip, but Brad and I were both so happy to come back home and snuggle our respective pups. Picture of Puppy Finn and Brad below, cuddling on the kitchen floor upon our arrival.

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