How my Misadventure in the Windy City Sold me on TSA PreCheck

In March 2021, I was restless. A few months prior, I had made the terrifying decision to take a semester off from grad school to deal with my mental health, and I really wasn’t sure I was ever going to be able to finish the program. I was so disappointed in myself. I felt like a failure. Needless to say, I needed a bit of joy in my life.

Around that time, I convinced my friend Syd to join me on a trip to Chicago the following month. Syd and I met during our time as Peace Corps Volunteers in Ghana. We hadn’t seen each other in person since our unexpected evacuation from the county in 2020 (… that’s a story for another day).

This was my first trip to the Windy City; it was love at first sight. I found the Chicago skyline incomparable to any other I had ever seen. All in all, it was a lovely trip to catch up with a friend.

The morning of our flight out of the city, I woke early to finish packing. I was exhausted, so I moved slower than usual. Our accommodations were only a two-minute walk from a train line that stopped right under O’HARE Airport, so we weren’t worried about transportation. Yet, after the third lengthy stop on the train, I thought, okay. We definitely should have been concerned. As a chronically late individual, flights are the only events to which I always arrive on time.

So, the thought that I was on track to miss this flight was anxiety-inducing. Syd and I had spent the entire week-long trip in a giggling frenzy. But now, sitting in this idled train, nothing was funny anymore. Any chit-chat between us was put on hold until further notice.

When we finally reached the airport, I only had about 45 minutes to check-in. Luckily for Syd, her flight was later in the day. Even though I knew my chances of making that flight were slim, I hastily made my way to security. When I arrived at the security checkpoint, I took one look at the line and deflated like a sad little balloon that never really had a chance. Even then, I stayed in line for over 30 minutes and went through security.

By the time I made it to my gate, surprise! I missed the flight. I spent the next three hours trying to book another flight to Boston, but for the strangest reason, there wouldn’t be any flights to Boston for a couple of days. I finally managed to secure a flight to New York departing the following day.

Suddenly, I had an extra day in Chicago. My first order of business was to book accommodation for the night. I turned to Airbnb, and I found a decent place to stay. I booked an Uber, and 15-20 minutes later, I was pulling up to a trailer park. There’s been a mistake, I thought. I pulled up the Airbnb app to confirm the address. It was not a mistake. Somehow, the listing advertising “an outdoor lover paradise” with hiking trails and bike trails forgot to mention it was a trailer.

That seemed like an intentional omission. 30 minutes later, I was heading to an overpriced room at the Hilton at O’Hare.

The following day, I took a flight to New York. I was on standby for a flight to Boston, but when they bumped me to a later flight, I knew it was time to take the scenic route home. So, I headed straight to the Grand Central Train Station.

This is a longwinded way of explaining why I enrolled in TSA PreCheck. In fact, I have Global Entry, which includes PreCheck. I am often tempted to gate-keep this travel time saver, but the cat has been out of the bag, as evidenced by the longer PreCheck lines. The first time I used my PreCheck benefits, I was traveling with my pup, Maia.

The benefit of not having to remove your shoes or the laptop from your bag while maneuvering a dog was worth every second spent completing the tedious application and stressing out over securing a coveted interview slot.

The quick overview

TSA PreCheck and Global Entry are trusted traveler programs designed to streamline and expedite airport security and customs processes for eligible individuals. TSA PreCheck allows pre-approved passengers to experience a more efficient security screening at domestic airports, while Global Entry is tailored for international travel and provides expedited clearance through customs and immigration for pre-screened travelers arriving in the United States.

Both programs aim to enhance travel convenience and save time. Another perk: many credit cards reimburse the cost of enrollment. Check with your card issuer to see whether yours participates.

Adventure abound! Until next time, Wanderers.