Chicago for the Weekend

deep dish pizza

Day 1 – Friday

Having signed up for the VIP package at the Chicago Triathlon, I was excited and ready to go. My original running partner couldn’t make it, so I asked my business partner, Lisa Gordon, to join me.

Hilary Topper with Bike Bag

After arriving at O’Hare Airport separately, we met up at the baggage area and headed to our accommodations at the Hotel Chicago.

After settling in, we headed to Grant Park Bistro for lunch. Our matching tee shirts sparked a conversation with fellow diners who had read about me on the Chicago Triathlon website. It was a nice surprise to meet people interested in my book.

Sitting at a cafe in Chicago

First Talk

My first motivational talk was scheduled for 3 p.m. at the Boulevard Room in the Hotel Chicago. Despite being tired from the travel, the energy of the crowd was infectious and the presentation went well. The talk was even live-streamed by the Chicago Triathlon marketing team.

Hilary Topper talking in Chicago

Chicago Firehouse Restaurant

Hilary and Lisa selfie

We dined at the Chicago Firehouse Restaurant that evening. The food was excellent and the atmosphere, set in an old firehouse, was unique. However, the night ended with a minor hiccup as I had left my credit card at the restaurant.

Firehouse Cafe

Day 2 – Saturday

Knowing that the day would be intense, Lisa and I had planned out a schedule. We started early, checking the bike’s gears and heading for breakfast at Grant Park Bistro. The rest of the day was filled with presentations, getting the bike to the race site, shipping unsold books, and preparing for the race.

The first presentation of the day didn’t go as well as I had hoped, but the second one was much better. The engaging questions from the participants made the effort worthwhile.

Hilary Topper with woman who bought book

After dropping off the remaining books at the expo and checking the bike with the valet, we walked to the race site. Despite the exhaustion, I was excited for the next day’s race.

at pizza place in chicago

The day ended with a delicious meal at Pizano’s Pizza. The deep-dish pizza and pasta were just what we needed after a long day. We took an Uber back to the hotel and turned in early, ready for the race the next day.

deep dish pizza

Day 3 – Sunday

With the break of dawn, Lisa and I were up and about by 3:45 a.m. As adrenaline coursed through my veins, anticipation for the triathlon had me buzzing with energy, despite the early hour. Lisa, on the other hand, was preparing to head home.

Hilary Topper with QR Triathlon Bike

I arrived at the race site via an Uber, saving my energy for the task ahead. However, upon arrival, I was met with an unexpected announcement: “No swim today. Swim portion canceled due to high winds.” The news was disappointing, but safety had to come first.

The triathlon had now become a duathlon, with the swimming portion replaced by additional running. Even with this change, the spirit of the event remained undeterred. As I cycled through the heart of Chicago and ran along its beautiful waterfront, I could feel the city’s energy propelling me forward.

Post Race

Hilary Finishing Chicago Triathlon

After the race, I returned to my hotel room with a sense of accomplishment mingled with exhaustion. My body was sore and my knee throbbed with pain, but the satisfaction of completing the race overshadowed the discomfort. It took me a couple of hours to dismantle my bike and pack it up for the journey home.

For dinner, I decided on Kitty O’Sheas, a pub conveniently located within the Hotel Chicago. I indulged in a comforting cheeseburger and fries, a well-deserved treat after the day’s exertions.

By 6:30 p.m., with my hunger satiated, I surrendered to my fatigue and fell into a deep sleep.

Day 4 – Monday

My last day in Chicago began with a hearty breakfast at Grant Park Bistro. I treated myself to eggs and a delectable biscuit, a small luxury after the grueling race. Despite a minor hiccup with a credit card convenience fee, the experience was enjoyable.

A minivan whisked me off to the airport, marking the end of my Chicago adventure. Despite the physical toll, the weekend had been filled with excitement, camaraderie, and personal achievement. As my plane soared above the city, I found myself already looking forward to my next visit to the Windy City.