For the first time in literary studies, a comparative analysis of the urbanistic poetry of Bohdan Ihor Antonych and Georg Heym is realized. The common and divergent in semantic codes and characteristic practices from which the poetics of both authors grows are investigated. The city is the defining topos of modernist writing and the central category of the modernist worldview. In no other epoch did the city enjoy the attention of writers as at the end of the 19th century and in the first third of the 20th century. The modern city acquires its outlines only in the middle of the 18th century, and the modernist city from the second half of the 19th century, but especially in the early 20th century through dialectical denial and overcoming the «city of enlightenment». The metaphor of the sea and the semantics of the element, usually water, characterize expressionist speech. Expressionist lyrics are imbued with apocalyptic visions. Urban modernist poetry is an extrapolation of the inner world (states of consciousness) to the outer world. Negative fascination is a defining feature of urbanistic discourse in expressionist poetry. Expressionist urbanistic lyricism is a romantic revolt against urbanization as a defining structural element of the civilizational evolution of mankind, and demonization is the main instrument of criticism of the city in expressionist lyricism. Special attention is paid to the function of memory and remembrance in big-city modernist poetry. While in Heym, a representative of early expressionism in German literature, the city appears as a topos of the apocalypse, in Antonych, the picture of the city is significantly more differentiated – and figuratively, and tonally, and substantial. The thematic blurring of Heym's urban landscapes is opposed by Antonychʼs structural urban subtopoi, the key one being the square. Antonychʼs poetics moves from the concrete to the abstract; his apocalypse is more mundane, aestheticized and playful, and the trumpets of the last day trumpet in the squares, which lovers meet. Antonychʼs city is more vitalistic than Heimʼs, even when the lyrical subject inflicts a flood on him. Not only expressionist but also formalistic and cubist melodies are heard in it. The article uses methods of textual, paratext, and contextual analysis, method of distributive analysis, method of poetic analysis, method of semantic analysis, method of stylistic analysis, method of phonological analysis, hermeneutic and post-structuralist methods.