Travel Diary | A Weekend In The Midwest 🇺🇸

A car accident of sorts, bachelorette fun, epic Chicago views, and so much food!

THURSDAY

My journey to Chicago started off well.  I was, for once, pleasantly surprised to be sitting in an exit row with extra legroom and next to a very handsome young man.  The plane was small but brand new and I was feeling relatively okay about flying that day (I’m a recovering nervous flyer).  Seems ideal, right?  Not quite.  We got all settled in and buckled up, only to sit at the gate for nearly two hours, without communication from the pilots.  I wasn’t too bothered by it, but people around me were losing their minds and it was bringing out the worst in everyone.  The handsome guy sitting next to me?  He turned out to be a super whiny jerk about the situation because “he had PLANS, you know!” I tried my best to stay zen with all the chaos around me, but it definitely was a trying start.

I was on this new but surprisingly small plane to Chicago to attend a bachelorette for my sister-in-law to be.  Anya is marrying Adam’s youngest brother, Ben, this October.  You can read a bit more about them in my recap of our visit last summer.  Once the plane was en route, I binge watched HBO’s Barry, which was most enjoyable and almost distracted me from all the in-flight tension.  If you like a dark comedy and/or Bill Hader, you should check it out. When we finally landed, later than expected, Ben and Anya texted that they were ordering Thai food for dinner and my desperation to get to their place increased.  Nothing can soothe a weary traveler like Pad Thai.

My plan was to Uber to their apartment, but in classic O’Hare fashion, a bunch of flights had all landed at the same time because of earlier thunderstorms.  Prices had surged and I was unsure of where to catch the Uber.  I decided to be basic and hop in a cab instead.  I was in no state to be making decisions, I just wanted noodles!  We sat in traffic for what felt like a lifetime and the driver and I passed the time chatting.  I was also starting to feel slightly motion sick, so when we hit another patch of traffic near the end of the ride, I was like, “are you freaking kidding me?” Turns out Ben and Anya’s new place is right by Wrigley Field and a Cubs game was just getting out, so there were hundreds of pedestrians and cars in this one concentrated area.  We spent like 15 minutes just trying to travel a few blocks.  I told him I’d just walk, but he said it he was stuck anyway and determined to deliver me to their front door as intended.  At last, we made a left turn, stopped in a line of cars and he pointed to their building. I thanked him and paid, threw my backpack on and reminded him that I needed to grab my suitcase from the trunk.  In what I can only describe as a total fluke accident and something that would, of course, totally happen to me, as I opened the door and started to exit the car, the driver tried to throw the car into park, except he accidentally accelerated instead of braking.  The car launched forward at great speed and the force of it flung me out the car door and started to drag me.  I let out an uncontrollable scream and was, for a brief second, convinced that this was probably it.  I managed to let go of the door handle, bounced off the pavement, and landed on my back in a daze.  Thank goodness I had put my backpack on, or I’d have seriously injured my back and head.  Once I realized that I was alive and relatively unscathed, I was overcome with immense gratitude to have survived and jumped to my feet with joy.  People around flocked and were asking if I was okay and I said yes, but could also see that I was bleeding and already felt sore.  I walked the 4 or 5 car lengths towards the cab (I know it was an accident, but how do you accelerate THAT hard and that far?) and the driver was absolutely distraught.  I’m pretty sure he must have thought he’d killed me.  Wasn’t my time though, and we both made sure we were okay and he asked my name and we hugged.  It felt like we’d been through a lot together, you know?  I now had my suitcase in tow and hoards of drunk baseball fans still crowded the streets.  Being in shock but trying to act like I wasn’t just thrown from a moving vehicle, I decided to call Adam before going to Ben and Anya’s, as I was on the verge of tears and quite shaken up.

It’s kind of funny now to think of how Ben and Anya must have felt opening the door to find me bleeding.  I had to tend to my wounds, wash my jeans, ice my elbows and knee and put a bunch of bandages on, but I was, at last, able to enjoy my comforting Thai stirfry – I’d earned it!  I’ll spare the internet a photo of the giant black bruise on my bottom that took up my entire left cheek.  Instead, you can see my bruised arms below, though this was 3 days later, so cuts looked much better.  The human body is quite resilient!

FRIDAY + SATURDAY

The next morning, the bachelorette began as we drove to Michigan.  I was excited about our Midwest road trip because I’d only ever been to Ann Arbor back in 2010.  We were staying in South Haven, MI, a gorgeous beach town that Anya spent many memorable summers as a kid.  As life goes, this sunny destination had only rain in the forecast for our time there.  We managed to get one patio lunch in before the dark storm clouds rolled in and the rain began.

Without going into too much detail, highlights included rocking matching colourful wigs and dancing the night away at The Dunes Resort, doing my very first shotski at The Idler Riverboat, a delicious breakfast at The Southerner in Saugatuk, and ice cream at Sherman’s.  Have you ever been to South Haven and/or Saugatuk?

SUNDAY

The sun had gone down and the warmth of the evening was wearing off as we walked back towards the apartment.  It was what appeared to be a typically populated Sunday night in Boystown and we were all feeling buzzed from our unexpectedly wine-fuelled dinner.  My brother-in-law Ben puts his arm out to stop his fiancé and I.  “Okay, here’s what I’m thinking,” he says, “We duck into this courtyard to finish off this bottle of wine, and then get our tarot cards read!”  Anya and I looked across the street at the tarot reading sign, and then at each other, both a bit unsure. I’d never had a tarot card reading before, but have secretly always wanted to.  We all jaywalk towards the neon psychic sign with curiosity.  A woman looks up from her phone to open the door and we found ourselves in a stark room that reminded me of a dental office waiting area that hasn’t been updated this century.  The three of us clumsily pile onto a cushioned bench in front of the window, as this woman tried to calm the nervous energy in the room by explaining her services. We don’t say much, except for Ben asking if she had wine glasses for us, which she did not have or find particularly amusing.  Feeling suddenly brave and curious, I blurt out,“I’ll go first!” 

Ben and Anya left, as she required one person in the room at a time for a genuine reading.  The silence was so uncomfortable, my breathing was now feeling exaggerated and audible.  She told me to think of a topic and a mantra as she shuffled the cards, and I kept repeating “clarity in my career” as she cut the deck and asked me to pick a card, ultimately laying some down in a circular formation.

The first card she flips over reads the word I dreaded the most: DEATH.  Which, based on what happened to me upon my arrival in Chicago, wasn’t a huge surprise.  Turns out that in the context of a career, it could mean a shift, which I have definitely been feeling for the past year.  She carries on to say that I am facing a lot of blocks within my work and that I am scared of receiving judgment.  Which, has been my life story for 2018, and so I am now VERY intrigued.  I don’t give her much back at all, just wondering what other pieces of information she might be right about.  She tells a story about Adam that is absolutely bang on, down to the name of the person and the conversation they had, and it’s so scarily accurate that she could have said anything after that and I’d interpret it as fact.  She adds that she’s pretty sure I own my own business and that if I do, I need to focus and do what I feel I need to.  That I keep being lazy, holding myself back and am not giving things 100%.  She said I need to stop caring about what people think and that I will ultimately help and influence people.  I was aghast.  I’ve been so scared of giving things my all.  I needed to hear every single thing she told me.

MONDAY

Sunlight streaming through the window, I am woken up to a pounding headache and am quickly reminded of the additional bottle of wine Ben and I finished after our tarot readings.  So unlike me, but I’m trying to cut loose and not take life so seriously all the time.  I smile remembering how much fun our night was.  A lowkey hangover is worth it.

My free day to explore started off with breakfast at a meat-free place called The Chicago Diner.  I’ve been a vegetarian my whole life, but ever since I figured out that I’m allergic to eggs, vegan meals are the only way I can enjoy breakfast.  It was tough to choose between an array of delicious options, but I settled on a tempeh and tofu scramble with faux gravy and biscuits.

After that, the only item on the agenda was to walk around.  I strolled past Wrigley Field and then made my way over to the Southport neighbourhood.  It felt very familiar, especially since the first store I saw was Lululemon.  I took my time going in and out of the shops and purchased some sale items at J.Crew.  I still had a few hours, so I decided to wander over to Lincoln Park.  Had a great time going into boutiques and ultimately ended up getting an Uber back to the apartment to freshen up before dinner.

On that last night, Anya had to fly to Austin for work, so after we had a lovely sister bonding dinner at Corridor Brewery, it was just Ben, and I.  Which, being that he’s lived away for all of the 11+ years I’ve known the family, we’d never before had this unique opportunity to hang out just us two.  I met him near his office downtown and we were going to check out some live jazz music, but it was such a beautiful night so we decided to pivot and instead went to the LondonHouse rooftop for a drink.  The sunset did not disappoint and it was special to be able to hang one on one with my brother in law!  Do you see the resemblance to Adam?

This city has a little spot in my heart, I feel so lucky to have an excuse to keep going back to Chicago for as long as Ben and Anya live there.  Have you ever been? What’s your favourite thing to do in the city?