Chicago has a pretty strong national reputation for being a very clean city. Unlike New York – where trash is put on the curb – Chicago is a city of alleys, so trash and debris is placed out of view. Trash is regularly picked up and streets are regularly swept.

Chicago has a reputation as one of the cleanest major "legacy" cities in the United States, especially when compared to peers like New York or Philadelphia. This is largely due to the city's unique architectural layout; unlike many older cities, Chicago was rebuilt after the Great Fire of 1871 with an extensive system of alleys. This means that trash collection and service deliveries happen behind the buildings rather than on the sidewalks, keeping the primary pedestrian walkways remarkably free of garbage bags and clutter. The city's Department of Streets and Sanitation is also notoriously aggressive about street sweeping and snow removal. However, "cleanliness" can vary by neighborhood; while the "Loop" and the "Magnificent Mile" are meticulously maintained to attract tourists and businesses, some outlying residential areas may face challenges with litter. Overall, the combination of the lakefront park system and the hidden alley infrastructure makes Chicago feel much more polished and "manicured" than most high-density American metropolises.