Travel Time: 11 hours (Driving)
If you’re family works as hard as mines does than, spring breaks are a great time to take a quick getaway. This year, was no exception and we choose to tour Chicago , the windy city, a mid western industrial age marvel with architectural grandeur and ghosts from prohibition’s past.
For her, a road trip to chicago had educational relevance; for me, it was a chance to come up for air. And from start to finish, the trip was perfect.
The Road Trip: 12 Hours of Music & Conversation
We left on a Tuesday morning around 9:30 AM, setting out on the long drive from Pennsylvania to Chicago. The journey took us west through Ohio, skirting the Great Lakes in Michigan, through Indiana, and finally into Illinois. With a couple of stops along the way, we arrived in Chicago late that night, around 9 or 10 PM.
The Music List
Road trips in our family always mean one thing: music. With a shared love for a wide variety of genres, our playlist branched off in countless directions, fitting 20 hours’ worth of music into a 12-hour drive. The conversation flowed just as freely, making the miles fly by. By the time we spotted the Chicago skyline in the distance, it felt like we had already experienced half the trip.
The return journey was smooth, even with a few thunderstorms along the way. By then, we had gotten so comfortable navigating the city that I didn’t need a map to drive around. We spent the ride home reflecting on the trip—Chicago’s architecture, its rich history, and its changing economic landscape. Before dark, we were back in Philly, tired but grateful for an incredible experience.
Where We Stayed: The Blake Hotel
Our home base for the trip was The Blake Hotel, a charming boutique hotel in downtown Chicago. It was exactly what I had hoped for—quaint, not overdone, and with spacious halls that didn’t feel crowded. The hotel had a quiet, relaxed atmosphere, perfect for unwinding after long days of exploring. Attached to it was a restaurant open only for breakfast and lunch, which worked out well since we wanted to venture out for dinner each night.
Located on Dearborn Street, the area around the hotel was lined with historic courthouses and federal buildings that influenced the local architecture. While some storefronts looked like they had seen better days, the mix of old and new made for an interesting backdrop to our stay.
Chicago’s Architecture: A Boat Tour Worth Taking
One of the trip’s highlights was the Chicago architecture boat tour. We booked through a company called P-Boat Tours, which launched from the mouth of the river. The 90-minute tour took us through the city’s iconic skyline, covering over 120 buildings designed by some of the world’s greatest architects.
Our guide, Gene, was exceptional—he had a background in architectural history and delivered an engaging, detailed lecture about the evolution of Chicago’s skyline. We learned about the influence of industry on the city’s development, the rise of skyscrapers, and the challenges of repurposing old industrial structures for modern use. The tour left me thinking about the future of cities like Chicago, built on an industrial foundation that no longer exists in the same way. While Amazon warehouses and distribution centers are moving in, they’re low, sprawling structures—far from the vertical giants that once defined the city’s business landscape.
After the tour, we stopped at Ghirardelli for the best hot chocolate I’ve ever had. From there, we walked past landmarks like the Chicago Tribune Tower and the University of Chicago Booth School of Business, snapping photos along the way.
Millennium Park and the Art Institute of Chicago
No visit to Chicago is complete without a stop at Millennium Park. We took pictures in front of Cloud Gate, better known as “The Bean,” and admired the park’s design. Just down the street is the Art Institute of Chicago, home to an impressive collection of European Impressionist art. The museum is massive, and we took our time exploring its galleries, taking in works by Monet, Van Gogh, and Picasso.
A fun touch: our hotel had provided us with a scavenger hunt challenge, which included finding the famous lion statues outside the museum.
Exploring Chicago’s Museums and Historic Sites
The next day was packed with some of Chicago’s best cultural and historical attractions. We started with a visit to Soldier Field, the legendary home of the Chicago Bears, before heading to the Adler Planetarium. The planetarium was a mind-blowing experience, reminding us of just how small we are in the vast universe.
From there, we moved on to the Field Museum of Natural History, where we explored exhibits covering everything from ancient civilizations to dinosaur fossils. Located right along Lake Michigan, the museum complex offered some of the best views in the city. We had originally planned to visit Shedd Aquarium, but it was closed that day—fortunately, we didn’t mind skipping it.
Dining in Chicago: The Good, the Bad, and the Overrated
We had several memorable meals throughout the trip, but one experience stood out—for all the wrong reasons. After hyping up Giordano’s, a famous deep-dish pizza spot, we left incredibly disappointed. The pizza was heavy, doughy, and just not what I expected. In hindsight, we should have gone to Gino’s East instead.
On a brighter note, we had a fantastic dinner at a small Chinese restaurant where she ordered miso soup and sushi rolls, while I had pad Thai. The atmosphere was quiet and relaxed—perfect after a long day of sightseeing. We had originally planned to eat in Chinatown, so that remained on our list for a future visit.
Final Thoughts
This trip was everything we needed—an escape from our demanding routines, a chance to experience one of America’s greatest cities, and a reminder of the beauty of learning outside the classroom or office. Chicago’s blend of history, architecture, and culture left us inspired, and the memories we made on this trip will stay with us forever.
There are still a few things we missed—the Skydeck at Willis Tower, the Lakers vs. Bulls game at the United Center, and some more local food spots we wanted to try. But that just gives us a reason to come back.
This wasn’t just a vacation. It was an experience—one I’ll always be thankful for.
