The Understudy Coffee and Books

Welcome to the Windy City, located along the shores of beautiful Lake Michigan. Chicago is a hustling and bustling city full of over 70 unique & charming neighborhoods, amazing food and iconic landmarks. Chicago has so much to offer, there is something for everyone to enjoy. Fun fact: Chicago is NOT the capital of Illinois, even though it is the most well known city in Illinois (We see you Springfield). This guide includes everything from popular tourist destinations to local stops by neighborhood and tons of restaurants to try. While this is not an all inclusive list of what to do in Chicago, but its a pretty good way to start with over 150 options and tons of personal favorites! Get ready to plan your weekend of fun in Chicago depending on what neighborhood you're located in. Get ready to put on your walking shoes, as you are sure to get plenty of steps in walking around the city. Immerse yourself in the melting pot of cultures. If you're searching for a specific day-to-day itinerary for Chicago, set up a call and I will help craft the perfect trip based on your needs. Even if you only have a day (which only would begin to scratch the surface) it is absolutely worth it to make a trip to downtown Chicago.

Chicago is filled with a vibrant energy fueled by its diverse BIPOC communities. This guide highlights Black, Indigenous, and People of Color-owned businesses, from delectable cuisine to bookstores and boutiques. Discover Chicago through a different lens that celebrates community.