Chicago: A First-Timer’s Reflections and Regrets
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When I decided to embark on the longest train ride in the US, from Chicago to Emeryville, California, aboard Amtrak’s California Zephyr, I knew I had to dedicate some time to the Midwestern city I’d never explored. So, I flew from New York City to Chicago two days before my train journey, checked into a couple of hotels, and set out to discover the sights. While I enjoyed my brief time in the Windy City, I left with a few regrets – lessons learned for a future return.
The Timing: A Winter Miscalculation
I’m a firm believer in getting to know a city on foot, immersing myself in its atmosphere by simply walking around. However, my first foray into Chicago was in February. A freezing February. With a stiff face, frigid fingertips, and cracked lips, I quickly realized the timing might have been… less than ideal. While the fresh snow sparkled and the icy Lake Michigan was mesmerizingly beautiful, a warmer season would have been a far more welcoming introduction to this incredible city.
Despite the cold, I persevered, exploring neighborhoods and even braving the beach. It was a mistake. While I appreciated getting acquainted with the city on foot, I couldn’t shake the feeling that these places would have been exponentially more enjoyable in warmer weather. Chicago boasts a wealth of indoor attractions, and I missed out on fully experiencing them.
Indoor Treasures Missed
Instead of shivering on a bench in Millennium Park, I could have spent the entire day lost in the Art Institute of Chicago, next door. This world-renowned museum houses over 300,000 artworks, featuring iconic artists like Georgia O’Keeffe and Vincent van Gogh. The Art Institute of Chicago is a must-see for any art enthusiast. It’s a regret I plan to rectify on my next visit.
Hotel Hopping: A Case of Too Much, Too Little
I decided to book a different hotel each night, hoping to get a feel for Chicago’s diverse hospitality scene. My first night was at theWit Chicago, a downtown Hilton hotel offering a whimsical take on modern luxury. I booked a Spa King Guestroom for $240, a corner room on the 16th floor with floor-to-ceiling windows. The asymmetrical mirrors, cartoonish light fixtures, and mismatched nightstands created a truly unique atmosphere. Soaking in the large tub with a view of downtown Chicago was an unexpectedly luxurious experience – one I regretted not extending for another night!
Neighborhood Overload
I attempted to explore several Chicago neighborhoods, from the Loop to Hyde Park, even venturing to the nearby town of Kenilworth. Looking back, I packed far too much into 48 hours. Instead of scratching the surface in so many places, I wish I’d focused on just one neighborhood and truly immersed myself in its character. Next time, that’s exactly what I’ll do. Chicago deserves a deeper dive, and I’m already planning my return.
Chicago is a city of contrasts, offering both breathtaking outdoor beauty and world-class indoor experiences. Learning from these initial regrets will undoubtedly lead to a more fulfilling and memorable visit in the future.
