Chicago, the third-largest city in the United States, is a city of bold architecture, vibrant neighborhoods, and legendary food. Nestled along the shores of Lake Michigan, it’s a place where history, culture, and modern energy blend seamlessly.
Trip Autumn 2024
My visit in September 2024, together with my girlfriend, was a whirlwind of iconic sights, local flavors, and a memorable wedding celebration.
We arrived late at night, the city lights shimmering as we took the train from O’Hare Airport into downtown. Our first meal? A quick stop at Taco Bell—sometimes, travel begins with the simple things.
Millennium Park & The Bean (Cloud Gate)
No visit to Chicago is complete without seeing the city’s most famous sculpture: Cloud Gate 🌎, affectionately known as “The Bean.” Designed by Anish Kapoor and unveiled in 2004, this 110-ton stainless steel marvel reflects the skyline and the energy of Millennium Park. Its seamless, mirror-like surface was inspired by liquid mercury, and you can actually walk underneath it—a surreal experience, especially on a sunny day when the city seems to wrap around you.
Millennium Park itself is a hub of activity, with open-air concerts, gardens, and the playful Crown Fountain. The park sits right in the heart of the Loop, making it a perfect starting point for exploring the city.
The Riverwalk & Architectural Cruise
After breakfast at Wildberry Bakery, we strolled to the Chicago Riverwalk 🌎. This 1.25-mile promenade along the Chicago River is divided into four districts, each with its own vibe—cafés, art installations, and river views abound. The Riverwalk is also the launch point for one of Chicago’s best experiences: the Architectural River Cruise.
The cruise is a must for anyone interested in the city’s skyline. Chicago is considered the birthplace of the skyscraper, and the tour guides bring the city’s architectural history to life as you glide past iconic buildings. Fun fact: the city’s unique “Chicago Style Bascule Bridge” design allows the bridges to open for river traffic using massive counterweights.
As the sun set, the city’s lights reflected off the water, and we enjoyed drinks with the wedding party along the illuminated river—a magical way to see Chicago at night.
The Wedding: Meyer’s Castle
The next day, we ventured outside the city to Meyer’s Castle 🌎, a historic mansion with lush grounds, for the wedding. The venue, just across the state line in Indiana, felt like a fairytale setting and offered a peaceful contrast to the city’s buzz.
Deep Dish Pizza at UNO Pizzeria
Back in Chicago, we couldn’t miss trying the city’s most famous dish: deep dish pizza. We headed to UNO Pizzeria 🌎, the birthplace of this culinary icon. The pizza is more like a savory pie, with a thick, buttery crust, layers of cheese, and chunky tomato sauce. It’s a true Chicago experience—delicious, filling, and best shared.
Trader Joe’s & Pumpkin Spice
A quick stop at Trader Joe’s let my girlfriend pick up some seasonal pumpkin spice—an American autumn ritual!
Starbucks Reserve Roastery
Later, we visited the Starbucks Reserve Roastery 🌎, one of only a handful in the world. This multi-level coffee wonderland offers unique brews, coffee-inspired cocktails, and a behind-the-scenes look at the roasting process. It’s a must for coffee lovers and a fun place to relax and recharge.
Blueman Group & Hotpot at Haidilao
That evening, we caught a performance by the Blueman Group 🌎 —a quirky, high-energy show that’s part music, part comedy, and all spectacle. For dinner, we joined friends at Haidilao 🌎, a popular hotpot restaurant, for a communal meal full of flavor and fun.
Lake Michigan & Farewell
On our last day, we enjoyed a leisurely brunch before heading to the beach on Lake Michigan. The city’s lakefront is a world of its own, with sandy shores and skyline views—a perfect spot to reflect on our trip before flying on to Seattle.
