Heliomorphic Chicago imagines the radical revision of Chicago’s urban form through optimized solar performance. The project makes new history by presenting a pair of counterfactual futures—two Chicagos that might have been. These alternative visions are modeled through specific parameters of solar access and ecological performance. The project presents alternative potentials for many of Chicago’s iconic buildings as opposing pairs, optimized in relation to either social equity or sustainable energy. Heliomorphic Chicago posits a pair of alternative histories for Chicago’s collective urban identity as derived from the simple, yet intractable, opposition of zero-sum economies —solar equity on one hand and solar energy on the other.