Liam Stanton argues that the current downtown discussion in Chicago is too optimistic about a return to its former glory, with office vacancy and many buildings operating far below their pre-pandemic occupancy levels. He argues that great cities often build on what comes next, rather than waiting for the past to return. Instead, he suggests creative solutions, including embracing winter markets, lighting, and winter programming across nearby streets to encourage visitors to explore multiple blocks rather than leaving one location. He suggests that Chicago should establish a “Loop Nights’s program, which includes predictable evening programming featuring music, food markets, public art and neighborhood festivals. Stanton also suggests rethinking restrictions on food carts, allowing food vendors to prepare food on carts, and creating a fast-track permit for small businesses. He also suggests that the city should use its unique alleys to become hidden destinations.