Chicago is a bit of an unusual lion; not only is he smaller than most (and either lives in or frequently visits the city), Chicago is a vegetarian. Chicago loves to eat vegetables so much that he even loves to play fun chasing games with kids where he has kids dress up as a vegetable and tries to catch them, especially as a broccoli since broccoli is Chicago's favorite vegetable. Though he still has his wild tendencies, his gentler side has earned him many friends on Sesame Street (as Mr. Handford had reassured him one time).
Although he was dropped as a major character in 1997, the puppet, often still played by Rudman, popped up occasionally from Season 33 onward (minus eyebrows). Chicago was also seen at the end of a Play with Me Sesame skit in which Super Grover comes in to save the day at the wrong time, mistaking the pretend noises the viewer makes for the real thing.
- Season 23: 2911, 2924, 2936, 2956, 2969, 2992, 2993, 2996, 3000
- Season 24: 3009, 3015, 3038, 3051, 3059, 3074, 3078
- Season 25: 3136, 3161, 3190, 3196
- Season 26: 3292
- Chicago, Illinois