109+ Chicago Trivia Questions to See How Much You Know!

Who founded Chicago? When did a massive fire break out in Chicago? It’s time to find out how much you know about this city with a beautiful skyline and architectural marvels. 

In this article, we have made a quiz with Chicago trivia questions to test your knowledge about this incredible city. 

The quiz is divided into sections based on its history, geography, local culture, restaurants, personalities, popular landmarks, and a variety of other interesting aspects. So, if you are up for challenging fun questions, here you go! Each question has four options and you have to choose the correct one. All the best!

Chicago trivia questions for kids

Que : Which Chicago street is famously known as the “Magnificent Mile”?
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Que : What is the name of the Chicago museum dedicated to the history of African American culture and contributions?
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Que : Which Chicago baseball team is known as the “White Sox”?
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Que : What famous Chicago-born writer authored “The Jungle,” a novel about the meatpacking industry?
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Que : Which Chicago skyscraper was the tallest building in the world when it was completed in 1973?
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Que : What iconic Chicago building was designed by architect Frank Lloyd Wright and completed in 1910?
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Informative Chicago Trivia Questions For Kids
Que : Which Chicago neighborhood is known for its vibrant Mexican-American culture and the annual Mexican Independence Day Parade?
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Que : Which Chicago institution is known for its extensive collection of scientific artifacts and educational exhibits, including a famous dinosaur exhibit?
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Que : What is the name of the Chicago-based sports network that covers local sports events and teams?
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Que : Which Chicago park is home to the historic Lincoln Park Zoo?
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Que : What is the name of the Chicago theater known for its long-running production of “The Lion King”?
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Que : Which Chicago bridge is known for its distinctive bascule design and often featured in photos of the city?
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Que : Which Chicago landmark, completed in 1914, was designed by architect Daniel Burnham and was originally known as the “Chicago Civic Center”?
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Que : What famous Chicago-born musician is known for hits like “The Chicago Blues” and “Sweet Home Chicago”?
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Que : Which Chicago museum houses a collection of over 300,000 objects and is known for its research in natural history?
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Que : What Chicago event, held annually in Grant Park, is known for its diverse lineup of music genres and large crowds?
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Educational Chicago Trivia Questions For Kids
Que : Which Chicago building was the tallest in the city before the completion of the Willis Tower?
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Que : What famous Chicago landmark is known for its beautiful mosaic ceiling and historic interior design?
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Que : Which Chicago neighborhood is known for its large Polish-American community and cultural festivals?
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Que : What is the name of the Chicago-based company known for its iconic deep-dish pizza and “stuffed pizza”?
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Que : Which Chicago festival, held in the summer, celebrates the city’s rich cultural diversity with music, food, and art?
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Que : What Chicago park features a large statue of Abraham Lincoln and is named after the 16th President of the United States?
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Que : Which famous Chicago-based comedian is known for creating the television show “Roseanne”?
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Que : What historical Chicago site is known for its role in the 1933 World’s Fair, also known as the Century of Progress Exposition?
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Que : Which Chicago neighborhood is known for its thriving music scene, including the historic Chicago blues clubs?
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Que : What iconic Chicago structure was the site of the 1893 World’s Columbian Exposition and features a large fountain?
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Insightful Chicago Trivia Questions For Kids
Que : Which Chicago-based actor is famous for his role in “The Blues Brothers” and has a building named after him in the city?
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Que : What is the name of the famous Chicago theater known for its improv comedy performances?
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Que : Which Chicago skyscraper, completed in 2009, is known for its eco-friendly design and distinctive shape?
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Que : Which Chicago street is famous for its historic architecture and the annual Chicago Architecture Biennial?
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Que : What Chicago museum is known for its interactive exhibits and is especially popular with families and children?
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Que : Which Chicago park, designed by Frederick Law Olmsted, features a large lagoon and is a popular spot for picnicking and outdoor activities?
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Que : What famous Chicago-born film director is known for movies like “The Untouchables” and “Ferris Bueller’s Day Off”?
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Que : Which Chicago festival celebrates the city’s history and culture with a large parade and various entertainment events?
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Que : What is the name of the Chicago-based music festival that showcases jazz, blues, and gospel performances?
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Wise Chicago Trivia Questions  For Kids
Que : Which Chicago-based company is known for its classic American hot dogs and has multiple locations across the city?
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Que : What is the name of the historic Chicago hotel that hosted the first national political convention of the Republican Party in 1860?
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Que : Which Chicago landmark is known for its modernist architecture and features a large outdoor sculpture by Pablo Picasso?
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Que : What Chicago museum is dedicated to the history of aviation and space exploration?
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Que : Which Chicago street is known for its vibrant nightlife, including bars, clubs, and restaurants?
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Que : What famous Chicago-born artist is known for his works of abstract expressionism and is associated with the Chicago Art Institute?
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Que : Which Chicago park is home to the iconic Buckingham Fountain, a popular tourist attraction?
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Que : What is the name of the annual Chicago event that features thousands of balloons, a parade, and family-friendly activities?
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Que : Which Chicago theater is known for its elaborate stage productions and has been a landmark in the city since 1921?
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Que : What Chicago-based sports team won the Stanley Cup in 2010, ending a 49-year championship drought?
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Que : Which famous Chicago neighborhood is known for its historic brownstone buildings and cultural diversity?
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Que : What is the name of the Chicago-based art museum that features a large collection of contemporary art?
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Savvy Chicago Trivia Questions For Kids
Que : Which Chicago-based company is known for its delicious Italian beef sandwiches and has been serving the city since 1938?
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Que : What Chicago landmark features a large clock tower and is known for its impressive Gothic Revival architecture?
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Que : Which Chicago museum is dedicated to the history of the city and features exhibits on Chicago’s past and present?
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Que : What is the name of the famous Chicago restaurant that is renowned for its steak and has been a dining staple since 1921?
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Que : Which Chicago neighborhood is known for its historic architecture and was a major site of the Great Chicago Fire in 1871?
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Que : What famous Chicago event is known for showcasing the city’s culinary diversity and includes food tastings from top chefs?
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Que : Which Chicago museum is home to the famous “Sue” the T. rex, one of the most complete dinosaur skeletons ever discovered?
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Que : What is the name of the annual Chicago festival that celebrates the city’s rich literary heritage with readings and book signings?
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Que : Which Chicago skyscraper is known for its distinctive shape and was designed by architect Mies van der Rohe?
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Que : What Chicago-based TV show, set in the city, is known for its portrayal of police and fire departments?
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Intelligent Chicago Trivia Questions For Kids
Que : Which Chicago street is known for its large selection of upscale shopping and luxury boutiques?
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Que : Which Chicago landmark was the first U.S. skyscraper to be built with a steel frame?
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Que : What is the name of the Chicago-based company known for its innovative office furniture and design?
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Que : Which Chicago-based organization is known for its extensive collection of rare books and manuscripts?
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Que : What iconic Chicago building, designed by Louis Sullivan, is often referred to as the “first modern skyscraper”?
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Que : Which Chicago neighborhood is famous for its vibrant Greek community and annual Greek Fest?
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Que : What historic Chicago venue is known for its association with famous jazz and blues musicians, including Louis Armstrong and Muddy Waters?
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Que : Which Chicago museum is dedicated to the history and culture of Chicago’s Polish-American community?
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Que : What popular Chicago event, held every December, features a large Christmas tree and festive holiday decorations?
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Resourceful Chicago Trivia Questions For Kids
Que : Which Chicago park features a large monument to the city’s founding and a historic band shell used for concerts and performances?
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Que : What is the name of the famous Chicago-based theater company known for producing works by contemporary playwrights and new adaptations of classics?
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Que : Which Chicago neighborhood is known for its historic brownstone buildings and has been featured in several films and television shows?
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Que : What historic Chicago building is renowned for its unique Gothic Revival architecture and is located on Michigan Avenue?
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Que : Which Chicago-based company is known for its iconic popcorn flavors and has been a city staple since 1979?
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Que : What Chicago-based film festival is known for showcasing independent films and is one of the largest in the country?
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Que : Which Chicago theater, established in 1921, is renowned for its Art Deco design and its famous “Chicago” musical?
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Que : What iconic Chicago building, completed in 1930, is known for its distinctive art deco architecture and was once the tallest building in the world?
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Que : Which Chicago-based nonprofit organization is dedicated to improving education and providing resources for youth in underserved communities?
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Thoughtful Chicago Trivia Questions For Kids
Que : What Chicago event, held annually in August, celebrates the city’s rich cultural diversity through music, food, and arts?
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Que : Which Chicago park, located along the lakefront, features the popular Lincoln Park Conservatory and a historic zoo?
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Que : What famous Chicago-based artist is known for his sculptures and public art installations, including the “Four Seasons” series?
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Que : Which Chicago neighborhood is known for its historic architecture and the annual Chicago Architecture Foundation Open House?
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Que : What is the name of the Chicago-based literary magazine known for its focus on poetry, fiction, and essays?
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Que : Which Chicago-based museum is dedicated to the history and culture of the Jewish-American community?
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Que : What Chicago-based company is known for its innovative technology in the field of health and wellness, including wearable fitness trackers?
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Que : Which Chicago theater is known for its elaborate stage productions and has been a key player in the city’s theater scene since the 1980s?
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Que : What is the name of the Chicago park known for its large art installations and beautiful views of Lake Michigan?
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Brainy Chicago Trivia Questions For Kids
Que : Which Chicago-based company is famous for its large collection of historic trains and transportation exhibits?
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Que : What Chicago event, held annually in September, celebrates the city’s culinary scene with food tastings and cooking demonstrations?
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Que : Which Chicago-based organization is dedicated to promoting and preserving the city’s rich cultural and architectural heritage?
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Que : What Chicago-based company is known for its unique line of handcrafted chocolates and gourmet treats?
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Que : Which Chicago neighborhood is known for its historic architecture and was the site of the 1893 World’s Columbian Exposition?
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Que : What Chicago-based event is famous for its large collection of vintage and antique items, attracting collectors from around the country?
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Que : What is the name of the Chicago park known for its large lagoon, historic boat houses, and scenic walking paths?
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Que : Which Chicago-based organization is known for its efforts in promoting environmental conservation and sustainability?
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Que : What famous Chicago landmark is known for its historic bronze statues and serves as a popular tourist attraction?
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Que : Which Chicago neighborhood is recognized for its vibrant arts scene, including numerous galleries and performance spaces?
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Que : What Chicago-based company is known for its innovative architectural designs and contributions to the city’s skyline?
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Que : Which Chicago park features the historic “Chicago’s Little Italy” neighborhood and a large community center?
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Que : What iconic Chicago event, held annually in June, celebrates the city’s LGBTQ+ community with a large parade and festival?
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Que : Which Chicago-based artist is famous for his public art installations and contributions to the city’s cultural landscape?
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Exploring Chicago through these trivia questions reveals just how rich and diverse the city’s history and culture are.

From iconic landmarks to vibrant neighborhoods, Chicago’s unique character shines through in every detail.

We hope these trivia questions have deepened your appreciation for the Windy City and inspired you to learn even more about this remarkable place

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