A Culture Lover’s Guide to Chicago

Explore 150 years of design in the Loop on an architecture tour, architecture river cruise, or walking tour for some of the best cultural experiences in Chicago. Spot recognizable Chicago cultural landmarks such as Marina City (affectionately dubbed the “Corn Cob Towers”), Aqua Tower, and the Tribune Tower, and leave with plenty of knowledge to use on a Chicago scavenger hunt.

As you meander below the stone and steel structures and awe-inspiring heights, you’ll also grasp the city’s history, culture, and politics through the lens of architecture.

Don’t miss: Oak Park is home to the Frank Lloyd Wright Home and Studio, the famed architect’s residence and workspace that you can now tour.

The World’s Columbian Exposition of 1893 transformed Chicago into a world-class center for art and design. The Art Institute of Chicago is not only one of the most renowned Chicago museums and art galleries, but it’s the only building from the fair still standing in the Loop.

Skip the ticket line and tour through history as you enter the expansive atrium and grand staircases which usher you to a permanent collection of more than 300,000 pieces ranging from textiles to sculptures and paintings.

Insider tip: For a great photo, stand just south of the stairs at the main entrance under the lion for a view of the animal sculptures, flags, and stone facade.

There’s no better place to experience the literary legacy throughout time than at the American Writers Museum, a one-of-a-kind interactive experience showcasing the talents of American writers in Chicago and beyond featuring reading spaces and activities appropriate for all ages. Write on a typewriter, glimpse treasures in a surprise bookshelf, and meet some of the literary giants that put Chicago on the arts and culture map.

Admission is included with a Chicago Explorer Pass. Have more time? Get to know more about Chicago and meet locals at the museum’s events which include trivia, literary happy hours, author talks, and more.

The Harold Washington Library Center covers an entire city block, and doles out more than just books on loan. Admire the exterior, a stoic brick structure embellished by allegorical features, such as the 12-foot (3.7-meter) owls alluding to knowledge. Inside, the 10 floors feature the single largest public art project in Chicago to date: a collection of 50 pieces in varying mediums.

For a reprieve from the bustling Loop, head to the top floor—the Winter Garden—for a lush, green, light-filled atrium perfect for soaking up sunshine in winter or cozying up with a book.

Just south of the Loop, Chicago’s Chinatown houses bars, restaurants, shops, art galleries, and more lining the streets of its architecturally stunning historic buildings. Book a culinary tour to sample the best sweet and savory treats or explore on your own.

Ping Tom Memorial Park is a wide expanse of greenery flanked by colorful murals and neighborhood history, and the glazed tiles of The Nine Dragon Wall and The Pui Tak Center pagoda are worth admiring before grabbing snacks at the neighborhood’s oldest bakery, Chiu Quon.

Related: Tour Guide York Chan’s Guide to Chicago’s Chinatown

Chicago’s far South Side was home to several industries, including the luxury railroad car manufacturer Pullman Palace Car Company. Workers settled in Pullman, the company’s planned industrial community that housed thousands in row houses from 1879–1897 and served as the setting of several national labor disputes.

Today, glimpse remnants of the fascinating and complicated historical place in Chicago on a guided tour of Pullman National Historical Park, the only to be nationally designated within the city limits. Architecture lovers, take note: Queen Anne and Gothic Revival reigned in Pullman’s design under the direction of famed Solon S. Beman.

Any Chicago guide for culture lovers isn’t complete without a nod to its live performance scene. From the Second City, an improv machine producing some of Saturday Night Live’s biggest names, to its renowned theater district, Chicago’s performing arts span the city’s geography and vast hometown talent.

One of the most entertaining experiences for culture lovers is a Drunk Shakespeare improv performance, tantalizing both literary lovers and comedy feigns alike. Grab a pint or non-alcoholic beverage—try Goose Island’s 312—and sit back to cringe, chortle, and delight in the experience.

The Great Migration of 1910–1970 brought millions of Black Americans from Southern states to northern cities. Though Chicago had a small African-American population before this historical period, the city credits much of its most beloved arts and culture to the contributions of those who arrived during this time.

Explore some of these impacts on an African-American heritage tour of Chicago. You’ll learn about the birth of gospel music, some of the city’s most influential Black leaders and innovators, and more as you explore historic South Side neighborhoods.

Densely packed with Middle Eastern and South Asian restaurants, grocery stores, elegant sari shops, Bollywood media, and more, the 2.5-mile (4-kilometer) stretch of Devon Avenue in Roger’s Park is one the most unique cultural experiences in Chicago.

Walking along the avenue, you’ll hear some of the 40 languages represented in the area and delight in culinary offerings spanning Israel and Iraq to India and Nepal. Sample falafel, curries, desserts, and more on a food tasting tour.