5 of the best architectural walking tours in Chicago


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 5 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 the 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 (among other buildings) along the way, your guide will regale you with stories and facts about them all, and about Chicago’s evolution into a great cultural metropolis after the World’s Columbian Exposition of 1893. From $29 per person.

Book at GetYourGuide

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, you’ll visit some of these masterpieces that are clustered downtown, including the world’s largest Tiffany stained glass mosaic and a vaulted ceiling, surrounded by Moorish details. There’ll also be a chance to admire several turn-of-the-century interiors renovated by iconic architect Frank Lloyd Wright. Any admission fees are all included in the tour price. From $34 per person.

Book at GetYourGuide

Chicago Walking Tour: Modern Architecture

Chicago’s urban topography hasn’t stood still over the years, and in more recent times a large number of contemporary buildings have been constructed across the city featuring a mix of international, modern and postmodern styles. During this two-hour stroll, your guide will show you several such edifices that showcase the city’s forward-thinking and original approach when it comes 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. From $30 per person.

Book at Viator

Food, History and Architecture Tour with Tastings

(Photo: Intrepid Urban Adventures / Courtesy GetYourGuide)

If your hunger for architecture is matched by your hunger to try some of Chicago’s famed culinary treats, this half-day tour could be for you. Starting under the dazzling marquee of the Chicago Theater, you’ll be shown around the bustling city, stopping off at various landmarks that showcase Chicago’s penchant for creative design, as well as a number of eateries where you’ll get to sample local dishes and delicacies such as Chicago-style hot dogs, deep-dish pizza, and Italian beef sandwiches. Among the places of engineering interest you’ll see along the way are the Chicago Pedway, a unique network of underground tunnels used by locals and commuters to navigate the city. From $98 per person.

Book at GetYourGuide

Private Chicago Architecture Tour

For a more intimate and exclusive experience, this three-hour private tour invites you to explore Chicago with a guide and a select group of family or friends. Over the course of the trip, you’ll be led to some of the city’s most legendary structures, such as Sears Tower, The John Hancock Building, historic brownstones, and the homes of Oak Park designed by beloved architect Frank Lloyd Wright. There’ll also be a chance to venture inside a handful of locations, with some admission fees included. The tour is also fully customisable to your preferences and tastes and includes hotel pick-up and drop-off. From $889 per group.

Book at Viator

By Paul Joseph