33. Travel: Chicago

I’ll never forget the first time I went to Chicago.  I was 26, and had been flying for (the now defunct) MarkAir for about six months. 

It was such a small airline, that we literally had three trips we flew:  a round-trip red-eye to Alaska, a three-leg epic journey from Seattle-Denver-Chicago-Newark (with a 10-hour layover, just enough time to sleep and do the flights in reverse), and the coveted San Diego trip, which was Seattle-San Francisco-Los Angeles-San Francisco-San Diego with a 24-hour layover in San Diego (you can see why we flight attendants would want that trip:  it was the only one with any time to see the destination city).  Chicago was not a city where we ever laid over.    
Until. 

Until one day in the middle of our Seattle/ Newark cross-country extravaganza, our plane broke down in Chicago.  Since it was not one of our bases (our bases were Anchorage and Seattle), we could not easily get it repaired (our airline was teetering on the edge of bankruptcy and was notorious for not paying bills—therefore, the contract workers in Chicago refused to fix our plane).  After three hours of sitting around waiting to see what would happen, the pilots made the decision that the crew desk needed to book us a hotel.  Finally, we were leaving the airport.    

Next thing you know, we were in scenic downtown Chicago!  If you’ve never been to Chicago, it reminded me of a smaller, kinder New York City.  And the lake! 


The lake was more like an ocean!  The shuttle van drove along the water’s edge while I gawked at its expansive glory.  And the wind!  The second we got out of the van, the wind whipped up and tried to blow us over.  It was only early May.  Our hotel was in a vintage brick building, and reminded me of something out of a movie set.

“What should we do first?” I asked the crew.  Since the airline was so small, I knew both pilots and the other two flight attendants (all four happened to be men) because we had flown together several times, and one of the pilots suggested Maggiano’s restaurant.  (As an aside, I’m sure you are familiar with Maggiano’s by now.  But the year was 1995, and the only Maggiano’s back then was the one in Chicago, the one where my crew and I would ultimately go eat dinner.)

 

We ate an incredible family-style meal, with a huge salad, mushroom ravioli, linguini, chicken, and for dessert, tiramisu.  I was in heaven. 

Next, we went to a comedy show.  I don’t remember who was headlining, but I do remember laughing until I cried.    

When we got back to the hotel, there was a message waiting for us.  We would pick up the rest of our trip tomorrow afternoon at the same time our original flight had been scheduled.  This meant we had all morning in Chicago, too! 

The next morning, I got up early and went for a walk along the lake.  I had not brought my running shoes because the trip was originally supposed to lay-over in Newark for only 10 hours.  This trip was when I really learned to pack for anything and “expect the unexpected.”

I ate breakfast at a small café, and then went to the Art Institute as soon as they opened. 

I did not spend as much time there as I wanted because I also wanted to do a bit of shopping.  In the back of my mind, I was very worried this might be my only trip to Chicago ever.  I wanted to see and do as much as possible in case I didn’t get the chance to come back (the irony being that after MarkAir went out of business, I was hired by United, whose training facilities and Worldwide Hub are, you guessed it, in Chicago).  I was constantly checking my watch, nervous that I would be gone too long and miss the shuttle van if I lost track of time. 

I arrived back to the hotel, packed my suitcase (including some new books and a sweater I had bought), and changed into my uniform.  I met the pilots and other flight attendants in the lobby 10 minutes before the shuttle bus arrived. 

It was the best trip to Chicago I never planned. 

MOV