Showcasing the best art and architecture of the Windy City, along with edgy shops and funky restaurants, Cool Chicago features the places that Chicagoans like to spend their time.

The book is an insider's guide to Chicago, written by a Chicago guide who wants to show off the best of her city – in this instance Kathleen Maguire (Author of Chicago Then and Now). The book first appeared in 2014 and has been totally revised for 2020.

Kathleen Maguire has compiled a diverse range of locations from must-see visitor attractions, to street art, to favorite local destinations. The familiar landmarks of the city are seen through the prism of Karl Mondon's experienced lens (travel books on Chicago, New York, Las Vegas, San Francisco, Portland, Phoenix, Seattle, Milwaukee, Vancouver, Toronto, Cleveland and Cincinnati).

Sites include: Cloud Gate, Crown Fountain, Pedway, Chagall's Four Seasons, The Berghoff, Flamingo, The Rookery, Quincy Street Station, The Ledge at Skydeck, French Market, Marina City, Garrett's Popcorn, Gene & Georgetti, Poetry Foundation, Driehaus Museum, Lakefront Trail, Chicago History Museum, Nature Boardwalk, Second City, Old Town Art Fair, Old Town Ale House, Schubas Tavern, Graceland Cemetery.