Of course we headed straight for the Chicago celebratory tote, but the creative duo behind MAPTOTE, Rachel (fashion stylist) and Michael (cartographer), offers representation of 15 different cities:

Each city comes with its own map, of course, but also reads with a locale-specific font (see MIAMI):

About MAPTOTE:

After a trip to Europe, Rachel Rheingold and Michael Berick wanted to create something they could do together. Combining their love and passion for travel, maps, and design – MAPTOTE was born. The simple cotton totes are silkscreened with fun schematic maps of various cities featuring their neighborhoods, city icons, and landmarks.

Black everyday tote, $20 (approx. 15" x 16")
natural grocery tote, $15 (also approx 15" x 16")