September 5, 2025

7 Hidden Architectural Gems You'll Discover on a River Cruise

While Chicago's famous skyline draws millions of visitors each year, the city's most captivating architectural secrets often hide in plain sight. Many of Chicago's lesser-known architectural treasures can only be fully appreciated from the unique vantage point of the water, where Chicago architecture tour reveal hidden details, forgotten histories, and stunning design elements that even longtime residents have never noticed. Here are seven architectural gems that will surprise and delight you during your river cruise adventure.

1. 333 West Wacker Drive - The Emerald Reflection

This curved glass giant follows the bend of the Chicago River, creating one of the most photographed reflections in the city. While many people recognize the building's distinctive green glass facade, few realize that its curved design was specifically created to maximize river views from every office. From the water, you can see how the building's form creates a perfect mirror of the sky and surrounding architecture, transforming throughout the day as light conditions change.

2. Reid Murdoch Building - Industrial Elegance

This massive former warehouse represents Chicago's industrial golden age, but its architectural sophistication is only apparent from the river. Built in 1914, the building's terra Chicago architecture cruise cotta details and classical proportions were designed to impress customers arriving by boat. The water perspective reveals intricate stonework and the building's role as a gateway between the industrial North Branch and downtown Chicago that's completely hidden from street-level views.

3. London Guarantee Building - Neoclassical Crown Jewel

Positioned at the river's edge, this 1923 Beaux-Arts masterpiece showcases elaborate terra cotta ornamentation that can only be appreciated from the water. The building's classical columns, decorative cornices, and sculptural details create a stunning contrast with surrounding modern towers. River cruise passengers are often amazed by the intricate craftsmanship visible in the building's upper floors, which remains invisible to pedestrians below.

4. Chicago River Locks - Engineering as Architecture

The Chicago Lock system represents one of the city's most impressive yet overlooked architectural achievements. These massive concrete structures, with their Art Deco-influenced design elements, control water flow between Lake Michigan and the Chicago River. From your river cruise, you'll witness this engineering marvel in action while appreciating the elegant design details that make functional infrastructure into architectural art.

5. R.R. Donnelley Building - Art Deco Crown

While the base of this building blends into the streetscape, its stunning Art Deco crown comes alive when viewed from the water. The building's setback design creates dramatic shadows and reveals intricate geometric patterns, decorative spandrels, and ornamental details that exemplify 1930s design sophistication. The river perspective showcases how the building's upper floors create a dialogue with the sky that's completely lost at ground level.

6. Chicago Riverwalk Pavilions - Modern Riverside Architecture

These contemporary structures along the Chicago Riverwalk represent some of the city's newest architectural innovations. Each pavilion features distinct design elements that respond Chicago boat architecture tour to their specific riverside locations, from the Marina Plaza's wave-like canopy to the River Theater's stepped seating carved into the riverbank. From the water, you can appreciate how these modern additions create a continuous architectural narrative along the river's edge.

7. Chicago Sun-Times Building - Modernist Riverside Statement

This sleek modernist structure showcases 1950s optimism with its horizontal emphasis and continuous ribbon windows. From the river, you can see how the building's design creates a strong geometric presence along the waterfront, with its clean lines and minimal ornamentation representing a dramatic departure from Chicago's traditional architectural vocabulary. The water view reveals the building's careful proportions and its relationship to the river that influenced its design.

Why These Gems Remain Hidden

These architectural treasures remain hidden because they were designed for a different era of the city - when the Chicago River was the primary transportation route and buildings competed for attention from passing boats rather than pedestrians. Today's busy sidewalks and towering new construction often obscure the very details that make these buildings special. River cruises restore the original viewing experience these architects intended.

The Stories Behind the Stones

Each of these hidden gems carries fascinating stories about Chicago's development, from the industrial boom that created massive warehouse districts to the technological innovations that enabled new building techniques. Expert tour guides bring these stories to life, explaining how each building represents a different chapter in Chicago's architectural evolution and how they collectively tell the story of American urban development.

Ready to discover Chicago's best-kept architectural secrets? Tours & Boats' Chicago Architecture Boat Tour takes you along all three branches of the Chicago River, revealing these hidden gems and many more. With expert guides who share the fascinating stories behind each building, you'll gain insider knowledge that transforms your understanding of Chicago's architectural legacy. Book your tour today and prepare to see the city's hidden treasures from the perfect vantage point.

Peter Drake is a Chicago native, writer, and self-proclaimed architecture nerd who’s been exploring the city’s streets, stories, and skyline for over 20 years. He founded All About Chicago to share honest, firsthand insights with travelers who want more than just a checklist experience. When he’s not digging into local history or hopping on a river cruise, Peter’s probably hunting down the city’s best Italian beef or debating whether it’s worth the hype.