Exploring by neighborhood is the best way to do Chicago. If you have multiple days in the city and you only stay downtown, that’s considered a fail in the locals’ book. Same goes if you try to traverse the North Side, West Side, and South Side all at once — you’re doing it wrong. Given that Chicago has over 77 neighborhoods and community areas, a successful day trip is more than doable but requires some strategy. Take the time to align your stops and you’ll see more of any given section of the city.
Here are three itineraries that maximize the number of neighborhoods you can pack in. Each day trip focuses on one main street as a base for exploring. Map out some pinpoints and go.