100+ Short Chicago Riddles With Answers
Think you know Chicago like the back of your hand? Test your local smarts with these short, simple, and fun riddles all about the Windy City. From deep-dish pizza and the Bean to Wrigley Field and the L train, this riddle collection will have every Chicagoan smiling and guessing.
- I’m tall, shiny, and shaped like a bean. What am I?
Answer: The Bean
- I roar at Soldier Field but I’m not a bear. What am I?
Answer: Chicago Bears fan
- I blow through the streets but have no lungs. What am I?
Answer: Wind
- I serve deep-dish with extra cheese. What am I?
Answer: Pizza
- I carry people under the ground. What am I?
Answer: Subway
- You ride me around the Loop. What am I?
Answer: The L train
- I’m a river but dyed green once a year. What am I?
Answer: Chicago River
- I light up the sky in Navy Pier. What am I?
Answer: Fireworks
- You can ride me with two wheels downtown. What am I?
Answer: Divvy bike
- I guard the city with a hat and badge. What am I?
Answer: Police
- I’m famous for jazz and blues. What city am I?
Answer: Chicago
- I stand tall with 108 floors. What am I?
Answer: Willis Tower
- I host the Cubs but I’m not a zoo. What am I?
Answer: Wrigley Field
- I serve up dogs with no ketchup. What am I?
Answer: Chicago-style hot dog
- I’m where the Bulls play. What arena am I?
Answer: United Center
- You visit me to see fish, not the sea. What am I?
Answer: Shedd Aquarium
- I hold stars but no sky. What am I?
Answer: Hollywood Walk of Fame (trick: not in Chicago!)
- I live in Lincoln Park but don’t grow. What am I?
Answer: Lincoln Park Zoo
- I’m filled with paintings and sculptures. What am I?
Answer: Art Institute of Chicago
- I shine lights on Broadway shows. What am I?
Answer: Chicago Theatre
- I freeze in winter and sparkle at night. What river am I?
Answer: Chicago River
- I buzz with shoppers on Michigan Ave. What am I?
Answer: The Magnificent Mile
- I go over water and help you cross. What am I?
Answer: Bridge
- I fly above O’Hare all day. What am I?
Answer: Plane
- You eat me with a fork — I’m not thin. What am I?
Answer: Deep-dish pizza
- I’m old, historic, and full of ghosts. What prison am I?
Answer: Joliet Prison
- I’m a flame that never goes out. What am I?
Answer: Eternal Flame
- I was once the Sears Tower. What am I now?
Answer: Willis Tower
- I’m Chicago’s lake neighbor. What am I?
Answer: Lake Michigan
- I spin you around at Navy Pier. What am I?
Answer: Ferris wheel
- I play music outdoors in summer. What am I?
Answer: Millennium Park concert
- I’m not a storm, but they call me windy. What city am I?
Answer: Chicago
- I’m frozen in January but great in July. What am I?
Answer: Lake Michigan
- I’m a nickname for Chicago. What am I?
Answer: Chi-Town
- I’m sold at every hot dog stand. What am I?
Answer: Italian beef
- I’m a tall green friend in Grant Park. What am I?
Answer: Buckingham Fountain
- I cut through downtown and go underground. What street am I?
Answer: Lower Wacker Drive
- I’m a Chicago pizza but I’m not deep. What style am I?
Answer: Tavern-style
- I sing the blues, I walk the beat. I live where jazz and pizza meet. What city am I?
Answer: Chicago
- I shine like glass and touch the sky. What building am I?
Answer: A skyscraper
- You hear me during the Chicago Air Show. What am I?
Answer: Jet
- I host concerts in Millennium Park. What am I?
Answer: Jay Pritzker Pavilion
- I go underground but I’m not a mole. What am I?
Answer: CTA subway
- I’m red, white, and run downtown. What am I?
Answer: CTA bus
- I’m the team with stripes and a soccer ball. Who am I?
Answer: Chicago Fire
- I bring crowds to Grant Park every summer. What am I?
Answer: Lollapalooza
- I’m the tower with a Skydeck. What am I?
Answer: Willis Tower
- You find me in every Chicago-style dog. I’m green and spicy. What am I?
Answer: Sport pepper
- I flash blue and red but don’t throw parties. What am I?
Answer: Police car
- I keep things cool by the lake. What breeze am I?
Answer: Lake breeze
- I have four stars but I’m not a hotel. What am I?
Answer: Chicago flag
- I race on the streets once a year. What event am I?
Answer: Chicago Marathon
- I’m tall, cold, and perfect for photos. What sculpture am I?
Answer: The Bean
- I’m the home of jazz, pizza, and pride. What city am I?
Answer: Chicago
- I light up Navy Pier at night. What am I?
Answer: Fireworks
- I house jellyfish and dolphins. What am I?
Answer: Shedd Aquarium
- I roar with fans in the South Side. What stadium am I?
Answer: Guaranteed Rate Field
- I snap photos of Bean selfies. What tourist am I?
Answer: Visitor
- I echo through Grant Park on July 4th. What am I?
Answer: Fireworks
- You take me from Midway to downtown. What train am I?
Answer: Orange Line
- I bring snow and wind in December. What am I?
Answer: Winter in Chicago
- I hold lions out front. What museum am I?
Answer: Art Institute of Chicago
- I’m a flavor of popcorn named after the city. What am I?
Answer: Chicago Mix
- I’m sweet and found on every corner. What treat am I?
Answer: Donut
- I’m long, flat, and connect neighborhoods. What am I?
Answer: Street
- I buzz in traffic but carry hot dogs. What vehicle am I?
Answer: Food truck
- I shelter books on every floor. What am I?
Answer: Chicago Public Library
- I’m sold in buckets and come in mix. What am I?
Answer: Garrett Popcorn
- I help you cross the river downtown. What am I?
Answer: Bridge
- You find me in Grant Park each August with music. What event am I?
Answer: Lollapalooza
How many did you guess right? Whether you’re a South Side local, North Side native, or just love Chicago from afar, these riddles hopefully brought some Windy City charm your way.