5 of the Best Architectural Walking Tours in Chicago

August 17, 2023

Chicago’s distinctive architecture extends far beyond its famous skyscrapers, with the city’s many uniquely designed buildings available to explore on guided walking tours.

(Photo: Chicago Architecture Center / Courtesy GetYourGuide)

From its steel-frame skyscrapers with terra cotta cladding pioneered in the 1880s to its more recently-acquired standing as the birthplace of modern architecture, Chicago has long been a laboratory for architectural innovation. Visitors to the city can discover the stories behind some of its most significant high-rises, museums, theatres, bridges, homes, schools, houses of worship and parks by joining a guided walking tour – and here are five of the best.

Treasures of the Golden Age Walking Tour

Chicago’s famous Loop district is positively teeming with landmark buildings from the late 19th and early 20th century. Hosted by an expert guide trained by the Chicago Architecture Center, this immersive two-hour tour offers visitors the chance to delve into the area’s rich architectural history and see how revival styles such as Beaux Arts, neo-Georgian and neo-Gothic came to embody downtown’s striking visual profile.

As you pass through the streets, stopping to admire many notable museums, department stores, skyscrapers and concert halls along the way, your guide will share stories and historical facts about these buildings and Chicago’s evolution into a major cultural metropolis following the World’s Columbian Exposition of 1893.

Price: From $29 per person.

Downtown Architectural Interiors Tour

(Photo: Inside Chicago Walking Tours / Courtesy GetYourGuide)

Among Chicago’s array of architectural gems are several buildings featuring eye-catching interiors that date back to the Roaring ‘20s, an era characterised by the class and elegance of the Art Deco style. On this two-hour tour, visitors explore several masterpieces clustered in the downtown area.

Highlights include the world’s largest Tiffany stained glass mosaic and a vaulted ceiling surrounded by Moorish decorative details. There is also the opportunity to admire several turn-of-the-century interiors renovated by the iconic architect Frank Lloyd Wright.

Admission fees to the buildings visited are included in the tour price.

Price: From $34 per person.

Chicago Walking Tour: Modern Architecture

Chicago’s urban landscape has continued to evolve over the years, with a large number of contemporary buildings constructed across the city featuring a mix of international, modern and postmodern architectural styles.

During this two-hour walking tour, your guide will introduce several impressive modern structures that showcase Chicago’s forward-thinking approach to architecture and design. Highlights include the elegant metal and glass tower of One South Dearborn and the Beaux-Arts-inspired exterior of the Harold Washington Library.

Price: From $30 per person.

Food, History and Architecture Tour with Tastings

(Photo: Intrepid Urban Adventures / Courtesy GetYourGuide)

If your appreciation for architecture is matched by your appetite for Chicago’s famous cuisine, this half-day experience offers the perfect combination.

The tour begins beneath the dazzling marquee of the Chicago Theater and guides visitors through the lively city streets, stopping at landmarks known for their creative architectural design. Along the way, you will also visit several eateries where you can sample local favourites such as Chicago-style hot dogs, deep-dish pizza and Italian beef sandwiches.

One of the most interesting engineering features included in the tour is the Chicago Pedway — a unique network of underground tunnels used by residents and commuters to move through the city.

Price: From $98 per person.

Private Chicago Architecture Tour

For travellers looking for a more personal experience, this three-hour private tour allows you to explore Chicago with a professional guide alongside your family or friends.

During the journey you’ll visit several of the city’s most legendary buildings and neighbourhoods, including the Sears Tower, the John Hancock Building, historic brownstones and homes in Oak Park designed by the renowned architect Frank Lloyd Wright.

The tour may also include entry into selected buildings, and the itinerary can be customised according to your preferences. Hotel pick-up and drop-off are also included for additional convenience.

Price: From $889 per group.

By Paul Joseph