Bobby and I decided to take our first real vacation together to visit Chicago! He grew up in Illinois and lived in Chicago for several years after college and all of his closest childhood and college friends still live there (or in the area) so it was a great chance to meet the important people in his life and learn more about his life. Since it was his city and his friends, I took a step back from my normal “Type A” planning and let him arrange everything. That is pretty huge for me, y’all.

June 1, 2018 – Day 1

Our flight out was at 6:19am so we got up very, very early. I had dropped Elliott off at my dad’s house the night before so that was one less thing we had to worry about in the morning but man, we were cutting it close. Bobby had a work social the night before and was out late so it was a late night of packing and getting ready. I had looked up the weather the week before and it said the temperature all weekend would be mid-90s but when we checked Thursday night, it was saying 60s! I was NOT prepared… I packed mostly tank tops and sun dresses and it was too late to go back to my apartment to adjust. Such is life, right?

We managed to get up and out the door a little later than I was comfortable with but I had no doubt everything would work out and we would make our flight. At least, I kept telling myself that. They say you should get to the airport an hour before your boarding time but I knew with a flight that early and the fact that we were not checking bags would mean we had some flexibility. We parked the car and took a very slow, frustrating shuttle over, breezed through security, and made it to the gate with a few minutes to spare. Unfortunately, we did not have time for breakfast!

Bobby was nice enough to let me take the window seat while he braved the middle. He had to work and the guy next to him would not let him put the armrest down, so I know it was not very comfortable for him. I appreciated the window seat so much though because it allowed me to get a little nap in during the flight. As usual, I was freezing so I did my best to stay warm with what I had.

It was a smooth flight. We navigated the airport easily and purchased our train tickets for the weekend. Bobby told me a story about how he once accidentally bought 10 tickets so he stood at the ticket stands and sold them all off to make his money back. Sure enough, while we were in line, that happened to someone else. Apparently that is a common thing! Those machines were kind of wonky though so it did not surprise me too much.

We hopped on the Blue Line, headed towards the city. Our first stop: FOOD. We transferred to the Red Line and surfaced in the city. It. Was. Freezing. I got my jacket out but it was not enough. The cold and wind are not for this southern, hot-yoga-loving, gal. Luckily, Portillo’s was only a few blocks away. Bobby had told me all about them for weeks so I was excited to finally be able to try it (not to mention, we were both starving at this point). I was told they have great hot dogs but since we were going to a White Sox game in the evening, I should hold off on the Chicago hot dog. He said the best thing to get was the Italian Beef so I ordered it exactly how he loves it and it did NOT disappoint. I had never had one before and with the added mozzarella cheese and jalepenos, it was delicious. We shared some fries in an attempt to be ‘healthy’ and somehow managed to walk out of there without ordering a slice of their “famous chocolate cake.” 10/10, would recommend to a friend.

Our Airbnb host was meeting us at 11:30am so in an effort to save time, we took an Uber out to Roscoe Village. We had booked our flights weeks in advance and when we went to book our lodging, we learned that there was a huge conference of some sort going on and all of the hotels were booked and/or had an insanely high nightly rate. Luckily, Bobby managed to find an affordable Airbnb just outside of the city which worked out perfectly for us. The host gave us a quick tour of the place before heading out. Bobby needed to work and I was so exhausted so I took a 3 hour nap while he was much more productive.

I woke up (albeit, a little groggy) to get ready for our White Sox game. Bobby had coordinated with about 12 or so of his closest friends to all meet up before the game to tailgate and then go to the game as a group. I had been very, very nervous to meet everyone but also just because sometimes large group settings make me semi anxious in general. Bobby is a social, friendly guy so I knew his friends would be too… but they are important to him and he is important to me so I wanted to make a good impression and be liked. No pressure. We cleaned up and headed out the door in our Sox gear.

Unfortunately for me, the weather had not warmed up at all so our Uber took us over to a nearby North Face and I bought a little fleece. It turned out I would end up needing something a little warmer by the end of the night but for the time being, it was perfect. Bobby had packed a light jacket and was clearly so much better at braving the cold than I was.

There was a bar nextdoor, Northside Bar & Grill, so we stopped in for a quick shot of Bobby’s favorite: Jameson. Maybe a little buzz would warm me up some?!

We hopped on the train and headed towards Guaranteed Rate Field (where the White Sox play). What an interesting name, right? The area itself was a little sketchy but we were not there to tour the area, we were there to tailgate and go to the game! Some of his friends had staked out some spots in the parking lot and already had food and drinks flowing. I was still a little nervous walking up to everyone but they were so incredibly welcoming and made me feel right at home. I met his 3 best friends and a few other very close ones. Over the next couple of hours, more and more showed up and everyone was social and nice. Everyone made an effort to talk to me and ask me questions about myself (and tell me how great a guy Bob is). They were totally selling him to me but little do they know, I was already sold on him a long time ago. *awe*

The tailgate was great. In the sun I was warm and in the shade I was cold so I kept taking the jacket on and off, on and off, on and off. We snacked on chips, chicken wings, sausage, and burgers. I only had some chips and a chicken wing because I was holding out for the ‘best hot dog’ inside the stadium. I also managed to get… a little drunk in that time. We had already had a shot of Jameson before getting there but once we got there, Big James made me a vodka/soda. When that was empty, he made me another. I caught a glimpse of his bar-tending skills and he sure did have a heavy pour! No wonder I was feeling so good. The group took a round of shots, too, and I obviously could not sit out for that. When Becky and Brad showed up, she offered me a little to-go wine and I had that too. I was good to go. Becky was also nice enough to share her dual-layer jacket with me. Everyone was dressed like it was 80 degrees outside and I was shivering! I tried to not look cold but I guess they could all see it on my face and everyone was trying to keep me warm and block the wind. It was sweet.

We made our way inside the stadium and as promised, our first stop was to order the hot dogs. James (not Big James, there are 2!), Bobby, and I found a booth and I ordered one the same way they did as to fully experience the greatness. Two natives would know more than I would! I skipped ordering a drink and chose water instead; I know my limits. Everyone had kind of gone their own way so we made our way to our seats. The hot dog was amazing and I spilled mustard on my jeans (not surprising). Everyone spent the next maybe 30 minutes coming and going, eating and drinks, and “watching” the game. (Note: I do not think anyone actually watched the game.). A few guys had gone to the bar below the stadium so after it got too cold, the rest of us joined them. It was much warmer out of the wind so I was glad to be down there. They drank and we all socialized until the game was over. This group was a hoot. I really enjoyed talking to everyone and getting to know them and hear stories about Bobby.

Just before the game ended, half the group (who lived outside of the city and who had driven to the game), took off. The rest of us decided to head out to Old Town to go to a bar. As we left the game, fireworks started (the White Sox surprisingly won 7-3)! It does not matter how old you are, fireworks are always nice. We waited at the train with everyone else and managed to grab some seats once on board. They were all reminiscing on old memories and sharing stories so it was difficult for me to keep up and know what was going on but Becky, the only other girl there the whole night, was very good at pausing and catching me up to help keep me in the loop. Girl power.

By the time we made it to Old Town, I had sobered up a bit and was back to feeling like a popsicle. My teeth were chattering, loudly. I do not know how everyone was managing with just a lightweight jacket. Becky shared one of her layers with me again which helped but by that point, I could not stop the chattering. It was so embarrassing.

Andy chose the bar for us, a place called Benchmark. I prefer a more dive-y place but it was a fun time. It was packed and it was loud but Andy knew everyone it seemed and had drinks ordered for everyone in matter of seconds. Impressive. I got a glass of wine and we went to the upstairs section and grabbed some tables. Over the next who-knows-how-long, we all went from drunk to dRuNk. Everyone probably had at least 2 drinks and Bobby bought a round of shots so things were getting dicey. I got to witness Bobby’s amazing dance moves and the whole group was making me laugh. Me being me, I started getting hungry and asking if we were getting food. Brad started a food countdown but when he got to the 3 minute mark, Bobby randomly decided it was time for us to head out. Looking back, that was probably a good call. It was definitely time to go.

He and I made our way through the crowds to the streets. I did not know enough about the trains to navigate our way home so I thought it would be best to just take an Uber home. That turned out to be way more difficult than I thought because I had no idea what the address of the Airbnb was! It was a struggle getting but I eventually found the place in my own email’s Trash folder and we were in a car shortly after. Whew. Bobby instantly fell asleep. After only 3 hours of sleep the night before, no nap on the plane, no nap before the game, and then a night out… I was surprised he had made it as long as he had. It was impressive. The Uber driver was chatty and I barely remember what we talked about and before we knew it, we were home. Bobby and I both had a set of keys, thankfully, and after a brief struggle between the door and me, we made it inside. We both fell asleep the moment our heads hit the pillows. Out.

June 2, 2018 – Day 2

As you probably could imagine, we slept in late. We needed it. When we finally got going for the day, we made our way back to Old Town to have brunch at Happy Camper. Thankfully it was much warmer outside. This place was pretty cool, very trendy, very hipster. It is a pizza place but since we were going to go to a real Chicago pizza place later, we shared a pulled-pork brunch dish and mozzarella sticks (which, to our surprise, were not fried cheese… but instead bread with cheese on a top and a side of marinara). We ate, had a morning drink, and watched Tiger Woods play golf. I had been hungry but after we started eating and drinking, my stomach was kind of achy. I have never been good at being hungover!

By this point, it was mid-afternoon. We decided to start our walking tour and made our way over to Navy Pier. We walked past the Trump Tower, walked along the river, and explored parts of the city even he had not been to yet. I loved strolling through the city, aimlessly wandering, hand in hand together. We people watched and just enjoyed each other’s company.

Eventually, we made it to Navy Pier and walked along it. It was warming up and the sun was starting to come out so it was nice. Lake Michigan was amazing; it really did look like an ocean, just going on and on forever into the distance. The Pier had several fun activities, restaurants, and all sorts of things to do on it. We opted out of those things in favor of just walking and soaking in the sights and people watching. There was an indoor section that we decided to go in and inside was the most beautiful 6-foot tall atrium. It was Bobby’s decision to go inside initially so I credit him for that great find! On our way out, Bobby came THISCLOSE to being pooped on by a bird. It literally landed mere centimeters in front of him. Thankfully, he dodged that bullet!

We had made our way back the front so we decided it was time to head out. We cut through Jane Addams Memorial Park and walked down Lake Shore Drive along the water. Our plan was to grab a drink at the Hancock Tower then maybe meet up with some of his friends again but we were both feeling a little exhausted from the night before that we decided to just keep it the two of us for the time being and check-in with his friends the next day. I struggled with helping make that decision because while I loved the idea of it just being us for the day, I did not want to be the type of girlfriend who held him back from seeing his friends the one time he was in town. It all ended up working out though.

Our walk continued through Lake Shore Park, past the Museum of Contemporary Art (we did not stop inside), and then over to the Signature Room at the 95th in the Hancock Tower where we enjoyed very expensive but very delicious drinks. The elevator took us up and we exited in the restaurant. From there, we wanted to see the view so we went to the windows instead of going upstairs to the bar and we were politely told to go directly upstairs (e.g. we got scolded in a nice way). We sat at the bar and socialized for a bit. The views were tough because it was a bit cloudy but they were still amazing. I ordered a Rose Sangria which quite possibly could have been the tastiest drink I had ever had in my life and Bobby got his favorite: an Old Fashioned. My stomach actually started to feel better after that drink so maybe it was a bit magical, too.

Our next stop was the Water Tower Place (a large, indoor vertical mall). We stopped inside the mall and went to a few different floors just to look around. I ended up buying a pair of shorts at Express before we left. It was a completely different style of mall than I had ever seen so it was cool to see, but at the end of the day it was just a mall so how much time could we actually spend there? Both of us were children though and put our hands in the water fountain as we went down the escalator. The water looked so perfect… we just had to touch it!

We passed the Historic Water Tower, one of the few buildings to survive The Chicago Fire. As we would pass things or through our conversations, we constantly kept saying to each other, “let’s look that up later” and learning about The Chicago Fire was one of them. Bobby was mostly sure he knew the whole story but he wanted a knowledge check.

By this point, it was getting late and close to dinner time. We headed toward Giordano’s, his favorite pizza place, but made a quick pit-stop at Jake Melnick’s Corner Tap for a shot or Malort first. Bobby and all of his friends had talked about Malort and how awful it was but because taking a shot of it apparently made you a “real Chicagoan” so I did not have a choice. Bobby ordered a shot for both of us (that was nice that he was willing to torture himself with me) and immediately the bartender laughed. GREAT. Great first sign. He brought the drinks over and asked what the occasion was. Another bartender heard Bobby say it was my first time having it and asked if she could watch me take it! Bobby even wanted to record a video of my “Malort face” as I took it. Just HOW BAD was this stuff? The bartender brought me a small class of Coke to help “wash it down” too and a glass of water. I was genuinely scared of what I was just about to drink but I was no wuss and took it like a champ. Bobby ended up not getting video (whew) but apparently I did not make a “Malort face” so it would not have been an exciting video anyhow. Anyway, the shot was complete garbage. It was not a burning shot or initially bad, it went down easily. The “gotcha” was the most foul, horrendous, lingering after-taste. Oh my gosh, it was awful. I do not drink soda and I drank that Coke just to help wash the taste out of my mouth. What in the hell was that stuff? Instead of adding it to the list of things to look up later, I immediately googled it to learn about the poison I just digested. Was I going to die? Was this a trap?! It turned out it was not poison and I was not going to die but you can read about it here. I was a real Chicagoan now! Bobby downed his shot and told me he was proud of me. The things we do for love.

Now, it was definitely time for dinner. Not only were we hungry but we needed to get that bitter taste out of our mouths immediately. Giordano’s was across the street so thankfully we did not have a long ways to go. The place was really cool with a fun environment. Bobby is so picky about his pizza in Houston (which makes sense if you come from a place known for pizza) so I was very much looking forward to finally trying his beloved Giordano’s. Last time I was in the city, I tried Gino’s East which apparently is not as good but hey, how could I have known that? We ordered right away because it takes 45-60 minutes to make the pizza. We also ordered a cocktail to cap off the evening.

While we waited, we discussed the components of pizza, the big pizza debate of Chicago (which is better: Lou’s or Giordano’s), and the bizarre couple next to us. When the pizza arrived, it looked so amazing. The couple next to us laughed at us for taking a picture of it and taking a boomerang of the “cheese pull.” Rude. We could have been MUCH more touristy if you ask me but that is fine, at least we entertained them. Finally, we dove in and it did not disappoint. Wow. That was some truly amazing pizza. I understood why it was his favorite and could agree that nothing in Houston compared. The closest thing would be Star Pizza, which we often frequented back home. But even then… Star Pizza had nothing on Giordano’s. It was well worth the wait! We each had 2 slices and took the last 2 home with us, knowing we would enjoy the leftovers later.

Our bellies full, we started to head home. Bobby surprised me and suggested we go back to Portillo’s to try the famous chocolate cake. YES! We got on the train then realized we had actually already been near Portillo’s so after a quick turnaround on the train, we arrived. We ordered a piece but waited until we were home to eat it. On our way home, we finally looked up everything on our “let’s look that up later” list. I love that we both share the need to look up and learn more about things we do not know.

We made it home and devoured that cake in a matter of seconds. Yep, it was just as delicious as they advertised and as it looked. Even Bobby, someone who does not prefer chocolate, admitted it was great. I loved it.

It had a been a long day with a lot of walking so we called it a night and tried to watch a movie. The Airbnb did not have cable and the local channels had nothing on. Netflix was not working. Everything was broken! Just then, it started to rain. We fell asleep to the sound of the thunderstorm, a perfect way to end the day.

June 3, 2018 – Day 3

We got a little bit of an earlier start as to fit in as much stuff as we could for our last day. We split a breakfast at Wishbone, a cute restaurant nearby that the Airbnb host had recommended to us on the first day. It was a great breakfast but we did not want to get too full so we could enjoy a nice lunch in town.

After breakfast, we walked over to where Bobby’s old stomping grounds. He pointed out all of his old hangouts and important places along the way. That was probably my favorite part of the trip as I really enjoyed seeing him in his element and hearing more stories about when he lived there. We arrived at his old house: The Bro-lagio. You could tell he was happy to be back in the area. He took a few pictures out front and we continued on. I loved looking at all the different houses and brownstones. We were constantly looking up the prices of ones for sale and talked about which ones we liked and did not like. It would be a different way to live but I can appreciate the appeal of it. My favorite thing were all of the trees arching over the streets; it made for a beautiful walk.

We made our way down Clark Street through Wrigleyville and past Wrigley Field. I was not allowed to take a picture in front of it because “we are White Sox fans” but that was fine, I did not care either way. It was a great little area though! He told me all about how much it had changed since he lived there and we explored the area a bit. Although, is it exploring when he knows where everything is? The weather was perfect, in the mid-70s, so it was nice to walk around.

Our next stop was the Willis Tower to be tourists and visit the Skydeck. They said it would be about 2 hours and they were not wrong; our total time there from start to finish was just barely over 2 hours. The line to the top was short but the line to take photos instead the Skydeck was insane. In line, it was revealed that I had already been up there before and if I had, then why would I do it again? *oops* I did feel bad for dragging him up there but you cannot argue with a great view of the city from every direction and a cute Skydeck picture together, right? Again, the things we do for love! It was a long, miserable wait but we survived and I appreciated him for being a trooper and doing that with me. It was great people watching, if anything. Of course I had to buy the professional photos, too.

 

It was early afternoon and because of our light breakfast, we were starved. We made our way back to Old Town to meet up with his friends Brad and Becky again. Everyone met at The Rabbit Hole where Bobby and I grabbed a quick bite to eat. We all enjoyed some drinks, of course. Bobby ordered a “mystery beer and shot” which was kind of fun. The place was cute; the windows were open to the outside so it was nice to have the sun on us and there were table-top games (that we did not end up playing).

Afterward, we started our afternoon bar hop. Our first stop was Declan’s Irish Pub where everyone got Jameson and I got a lemon drop martini because I do not like whiskey. We hung out there for a bit, again a half indoor/half outdoor place. I liked how all the restaurants and bars were able to “open up” to the outside when it was a nice day. I know they cannot do that when it is freezing outside but on a nice day like it was, what a great option to have!

Next up was The Fireplace Inn where we all had “Huge Ass” vodka lemonades; their popular item. Those were very delicious but large and strong! Uh oh. It was nice to sit outside and hear all about their time working together in Chicago and more stories. Unfortunately, we were sitting in the shade so we made our way to a sunnier location.

I did not catch the name of our 4th place but there, I had my first Irish Car Bomb! We made a huge mess on the table when we dropped our shots but we were outside so it was fine. We also ordered cheese curds because I had said they sounded gross but they all called me on it and said I only made that accusation because of the word “curd.” Busted. We ordered them and they were fantastic. Y’all got me.

Our last stop was Woodie’s Flat where Becky and I finally contributed and bought a round fireball shots. The waitress asked me if we wanted a sparkler with it and I obviously said yes. No one knew though so it was a surprise to everyone when they came out with sparklers!

The sun was going to be going down soon and I wanted to be a tourist one more time an visit The Bean so we all said our goodbyes and parted ways. I had heard so much about them and loved getting to know them more. They were very kind to me and I appreciated how welcoming and inclusive they were. It was a great afternoon but the one thing I learned from it was that I cannot drink as much as a Chicagoan! I cannot speak for Bobby but I was preeeetty buzzed by that point.

We went to Cloud Gate (the Bean) and took some touristy photos. I had been there once before but it really is a great piece with the reflection of the surrounding buildings and whatnot. It was a beautiful night and a gorgeous sunset. I somehow managed to grab some kind of awesome snapshots of the skyline.

We had strangers take some photos for us and hung around the area for a little bit. We enjoyed one last drink at Park Grill and watched Game 2 of the NBA finals. I had a frozen something (no idea what) and from what I remember, it was good. It was the drink that pushed me over my limit and getting home was kind of rough. The bumpiness of the train was making me feel nauseated!

We made it home and instantly heated up the leftover Giordano’s. Not shockingly, the microwave did not work so our drunk patience was tested with having to wait on the oven. There were only 2 slices and it was definitely not enough; I think we both could have eaten at least one more slice. It was probably best that we did not have more though after how much we had ate and drank all weekend.

June 4, 2018 – Day 4

Our last day in Chicago was much more relaxed. Our flight was not until the evening so I slept in while Bobby got up and worked a little bit. We cleaned up, got ready to go home, and packed before the Airbnb host came by around 11:30am to pick up the keys. We made our way to the Brown Line one last time (the Paulina stop had been our nightmare all trip because the train always took forever). Our train pass was expired so we bought a one-way to the airport and made our way. It was quite the ride out there! I did not remember it being that long on the way but to be fair, we did stop for lunch on the way in and then used an Uber. We eventually made it to the airport.

Before our trip, we both registered for TSA-Pre Check. Our approval and travel ID did not come in time for our trip to Chicago but we had both received our official emails the day before so we were able to utilize our new fancy Pre-Check for the first time! Talk about a time saver. It was great to breeze through security.

We split chips/queso and a buffalo chicken sandwich at Chili’s before getting in line to board our flight. Our timing for that flight was perfect and made me much more comfortable than our one the other day. It was great to not rush or feel anxious. Bobby went to get us water and then we boarded swiftly, this time I took the middle seat. Teamwork.

WiFi on the plane was not working so Bobby could not work and instead, we worked on the in-flight magazine crossword puzzle. I had actually never done one for-real so he was teaching me and we were helping each other. I knew how they worked but it there are definitely tricks to filling it out. Afterward, I lent him my Sudoku book and taught him how to play it. What a bunch of nerds: doing crosswords and playing Sudoku the whole flight. I loved every second of it. When we landed, we stopped to buy me an easy crossword puzzle book and him an easy Sudoku book (flashforward: we both use our books just about every night now). Bobby also surprised me with a cookie he bought for us when he went to get the water. My hero.

We picked up the car and headed to my dad’s house to pick up Elliott. I always appreciate my dad and Suzette taking care of Elliott while I am away. He loves it there and I can trust he is loved in return.

Bobby and I decided to start the Keto diet after our trip so to finish off a weekend of poor eating and have one last carb-loaded meal, we stopped for Pei Wei on the way home. Worth it.

—

I had been told it is important to be able to travel well with your partner so I was so thankful that we had a fun, successful trip. There were moments I wish we had (or I had known of) more of a plan instead of winging it but I trusted him and it always worked out. We never ran out of things to talk about and I loved getting to see where is was from, meet his friends, and share the city with him. For some reason, I had always been a fan of Chicago and it did not let me down. My first time (and only ever time before) to the city was just for part of one day so to be able to experience it in its entirety with someone who knows it so well was perfect. I was worried about the weather but after the freezing Friday night, it warmed up and it was just as I hoped it would be. Everything was!

Thank you, Bobby, for taking me and inviting me to share in that part of your life! It was a wonderful trip and hopefully our first of many. 

Until next time,

Jillian