Watch “Chicago Architecture & The Magnificent Mile” Full “Travels with Darley” Episode
Chicago is a city that reaches for the sky — and along the legendary Magnificent Mile, history, architecture, food, and culture come together in unforgettable ways.
In this episode of Travels with Darley, I explore one of America’s most iconic stretches: Michigan Avenue’s Magnificent Mile. From soaring skyscrapers to deep-dish pizza, Gilded Age glamour to family-friendly fun, this Chicago adventure reveals why the Windy City remains a must-visit destination for travelers of every age and interest.
Watch the full episode below and come along for the journey!
Discover Chicago’s Architectural Legacy
Chicago is the birthplace of the modern skyscraper — and there’s no better way to experience it than from the water.
I join expert guide Adam Rubin from the Chicago Architecture Center to explore how innovation, resilience, and bold design shaped this skyline. Highlights include:
The stunning Wrigley Building
The historic Tribune Tower
The iconic John Hancock Center
A river cruise aboard Chicago’s First Lady, offering front-row views of more than 50 architectural masterpieces
We also go inside the historic Medinah Athletic Club (now part of the InterContinental Chicago), a hidden gem filled with ornate details and fascinating stories from Chicago’s glamorous past.
For thrill seekers, I head up 1,000 feet above the city to 360 Chicago at the former Hancock Center — and lean 30 degrees outward over Michigan Avenue during the Tilt experience!
Classic Chicago Eats (And Sweet Treats!)
No visit to Chicago is complete without indulging in its legendary food scene.
In this episode, I:
Savor deep-dish pizza at Gino’s East
Experience fire-torched dining at Casa Chi
Visit the world’s largest Starbucks Reserve Roastery
Enjoy a whimsical ice cream cart experience at the Four Seasons Chicago
Warm up with decadent chocolate at The Peninsula Hotel
Chicago proves that architecture isn’t the only thing stacked high here — the flavors are just as bold.
Historic Hotels & Gilded Age Glamour
The Magnificent Mile has long been a destination for luxury travelers.
Step inside:
The Drake Hotel, including the elegant Princess Diana Suite
The InterContinental Chicago’s historic spaces
The Peninsula Chicago’s rooftop ice skating rink
These grand properties tell the story of Chicago’s evolution from Gilded Age powerhouse to modern global city.
Family-Friendly Fun & Local Shopping
Chicago isn’t just for architecture buffs — it’s packed with experiences for families and culture lovers.
This episode includes:
American Girl Café
Museum of Ice Cream
The Shops at North Bridge
Behind-the-scenes access to the Magnificent Mile Lights Festival & Parade
Whether you’re shopping designer boutiques or enjoying holiday festivities, the Magnificent Mile delivers year-round excitement.
Why Visit the Magnificent Mile?
The Magnificent Mile isn’t just a shopping district — it’s a living timeline of Chicago’s innovation, ambition, and creativity.
Here, you can:
Cruise through architectural history
Dine at legendary restaurants
Stay in iconic hotels
Shop global brands and local favorites
Experience skyline views unlike anywhere else
It’s Chicago at its boldest and most beautiful.
Plan Your Chicago Adventure
If you’re dreaming of a Midwest getaway filled with world-class architecture, unforgettable food, and dynamic culture, Chicago should be at the top of your list.
Watch the episode above for insider tips and inspiration — and let the Windy City surprise you.