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How NOT to Travel in Chicago

5 Lessons I Learned So You Won't Have To

By Judey Kalchik Published 3 years ago Updated 3 years ago 6 min read
9
How NOT to Travel in Chicago
Photo by Lance Anderson on Unsplash

When I was in bookselling the month of May meant BEA- that's the Book Expo America. Pre-COVID is was held exclusively in New York City, but there was a time it floated between NYC, LA, and Chicago. The year after I moved to Michigan it was in Chicago and I was excited to attend.

The show was scheduled for the day after my vacation and I was determined to make the drive there from Ann Arbor. (It looks really close on the map, not even a thumb down the road.) In a hurry, I ducked into the office and picked up my badge and other information and went west.

A thumb away is farther than it looks, but I made good time. Until I hit the city. My plan was to check in at the hotel then get to the Convention Hall. Lost. I was hopelessly lost.

I drove around and around and then suddenly I saw it: The Convention Hall. A quick change of plans; books first and surely I could follow someone to the hotel later. It was wonderful: books, authors, books, lines, books, noise, books!

By Timon Studler on Unsplash

This was in the happy time when a badge with "Borders" on it made people smile, not wonder if we would honor their invoice. I met a lot of people, made many contacts, got tote bags, bookmarks, t-shirts, swag and books. Also- got directions to the glorious Chicago Holiday Inn.

With a minimum of effort I found the hotel, grabbed my suitcase and laptop and hurried to the front desk. Apologizing for the late check-in, I gave my name and Holiday Inn Preferred Membership card to the clerk.

My roommate, she informed me, was already checked-in.

Roommate? Rats. While not unheard of since we frequently shared rooms at company meetings, I wasn't expecting a roommate. There hadn't been any extra note in my info packet... but I hadn't made the arrangements myself. So be it. Roommate.

By Marten Bjork on Unsplash

As I let myself into the room I was relieved; she had chosen the "bed of doom" (the bed closest to the door), I saw the laptop, black computer bags, totes of books, clothes.... clothes everywhere. Great; a messie. Well, it was just for two nights.

Since the roomie wasn't in the room I dragged my stuff over to the bed by the window, set up my laptop, checked for email, as one did at the time. And realized I was hungry. It had been hours since I'd had that tea for breakfast and I'd tromped around the conference center for several hours.

Since this was my first time in Chicago I was hoping to get dinner with a group, but I had missed the meeting-before-the-meeting that happened during my vacation. I was on my own for the night.

By Joel Mott on Unsplash

So I left a note for the roomie and went out wandering down the Magnificent Mile. It was really wonderful, even yes: magnificent. I saw the giant Borders Bookstore on State Street. Bought some mixed cheese and caramel popcorn, wandered in and out of the stores. Avoided the American Girl mega-store successfully. Found a little Italian place and had antipasto and tiramisu.

Back at the hotel: still no roommate. I took a hurried shower, left messages all around the hotel for my coworkers, lit a candle, and sent even more email. No roommate. Great. All alone in the exciting city, getting more and more tired by the second.

I called the desk and left a wake-up call for 6:00 since I would need to do major time on my hair in order to be presentable. Blew out the candle and left a note on roomie's bed: "Hi! I'm Judey. See you tomorrow!" Left the security lock off the door, slipped on a t-shirt from the show as a nightshirt. Rolled over and---- out.

Until about 2:30, when Roomie came home. Drunk. Confused. Angry. And an utter stranger.

By Jen Theodore on Unsplash

She loomed over me: long blond hair, bleary, and shouting. Not at all impressed with me telling her I was Judey. Judey who? She didn't know a Judey. Judey-from-Operations wasn't any better. On no, oh no, oh no.

She wasn't from Borders. I am in a room with someone that ALSO didn't know she had a roommate. I was sleeping in a drunk, angry, tall, stranger's room.

The Valkyrie yelled that she was calling the police. I grabbed the phone and called the desk, and gave them my name and room number. Told them I had been put into the wrong room, if I wasn't down there in five minutes please come get me.

Then I ran around the room throwing my stuff into the suitcase. She is yelling at me the entire time. Screeching! I jumped into my jeans, grabbed the laptop case, suitcase, tote bags. Ran barefoot to the elevator and took it to the ground floor.

Let's take a moment so you understand what I looked like.

I had showered and let my hair air-dry: It was a smooshed-up nimbus all around me. I was barefoot. Braless. In a freebie book-themed t-shirt that did me no favors as it drifted over my jeans. Purse over one shoulder, laptop over the other, suitcase half-zipped and dragging beside me.

The clerk stared at me as I explained what happened: I wasn't supposed to have a roommate. There had been a mistake. I had been double-booked, but didn't know it. The real occupant had just come in. I needed a new room.

She looked me over, then said there weren't any rooms due to the expo. I knew there was a room: my room. I was a Holiday Inn Preferred Member. I needed my room. No, she said, no rooms.

Then she asked me: how long had I known this woman?

What? How long? Umm... about three minutes maybe, tops?

The desk clerk smiled a little and said "Sometimes when we are away from home, we do things we wouldn't normally do. We think things will be better than they turn out to be. That doesn't mean we owe you another room."

I'm sorry? We think....turn out to be...wouldn't normally... Holy cow: she thought I picked up this woman during the expo, we had a tiff and I was leaving her.

Things went rapidly downhill from there.

As it dawned on me how much bad could have happened, how I would have reacted to coming into my room to see Goldilocks sleeping there, how evidently no one knew where I was, how incredibly inebriated she was..

How much trouble they were in for exposing me to such danger! How interested their insurance company would be to find out what had happened! I was, madam, a Holiday Inn Preferred Member!

I got the room.

As the adrenalin wore off and exhaustion slid over me, just before I fell asleep I had two distinct thoughts:

  • My curling iron and makeup were still in the other room
  • The tall smashed Valkyrie was getting a wake-up call in about three hours
  • I checked out the next morning before I left for the expo. The day clerk was on duty so I had to go over the whole thing again. I was expecting to get the room comped but no, she explained I would still be charged. The real kicker, though, was when my purchasing card statement came in the next month: they had charged me for the room, alright. But they also charged me for the first one, too.

    I went to the expo and searched for the rightful room owner. Oh no- not to talk to her; to avoid her like the plague. If there was a tall blond woman around I was a ghost.

    Lessons I learned from this experience:

    1. Always check in to the hotel as early as possible.
    2. Lots of people use black laptops.
    3. Take pajamas you won't be embarrassed to be seen in in case of a fire... or in case you are sleeping in a stranger's room.
    4. The Holiday Inn Preferred Membership is not the mighty power I presumed it to be.
    5. Things aren't always what they seem, so give people the benefit of the doubt.

    _______________________________________________

    If you enjoyed this, or perhaps are simply glad it was me and not you, please click on the heart below to let me know.

    Here are a few other stories about my time in bookselling:

    humor
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    About the Creator

    Judey Kalchik

    It's my time to find and use my voice.

    Poetry, short stories, memories, and a lot of things I think and wish I'd known a long time ago.

    You can also find me on Medium

    And please follow me on Threads, too!

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