The El
Chicago's public train system, called "The El" for the elevated track it often runs on, is a great way to explore the city. Apple and Google maps can easily help you navigate to your destination via public transit. All stations, including the busses, accept wireless tap pay. Each ride is $2.50 regardless of boarding/exiting station. If you plan to make frequent trips on/off, consider buying a multi day or weekend pass.
Go check out my guide for the best free things to do as well as itineraries and travel tips to make your trip unforgettable.