Make your marriage proposal memorable in a stunning location! We're taking a look at some of the best places to propose in Chicago to help you plan out an epic wedding proposal in the Windy City.There's no shortage of locations in Chicago to propose. Here's our list of the perfect places to pop the question in the Windy City. Chicago has the 25th most diverse bird hotspot in the country. Popping the question in Chicago? Find the best places to propose in Chicago with real-life stories to help plan your romantic proposal! As Chicago's Top Proposal Planner we focus on custom, one-of-a-kind proposals. You have the vision we make it a reality! In this article we will tell you sixteen best places to propose in Chicago and details about each suggested propose places and some Chicago proposal Ideas.