Chicago is always brimming with energy and excitement, evident from its towering skyscrapers overlooking sandy beaches, to sun-filled baseball games at the Wrigley Field, twilight concerts in Millennium Park and fireworks at Navy Pier. Nicknamed the “Windy City”, Chicago is not only an international hub for technology, commerce and transportation but also is the spiritual home to Jazz and Blues music.
Chicago’s downtown area – The Loop governs the topography and the neighboring districts are named after their directional association with it. The chief districts of the city are:
The North Side
The West Side
The South Side
The Regional Transportation Authority (RTA) coordinates the operation of the three service boards: CTA, Metra, and Pace for smooth public transportation through Chicago.
As a visitor, the following information will be useful to you:
American-United Taxi: +1 773 248-7600
Checker Cab: +1 312 243-2537
Flash Cab: +1 773 561-1444 
Yellow Cab: +1 312 829-4222
Chicago in 3 days (Source: Frommers)
Chicago is home to several local specialities. For a complete Chicago experience, definitely sample these culinary treasures.
Refer here for more options.
Dive bars are a norm in Chicago city. Some popular options are:
Tipping is expected in most places and should always be done unless the service provided was completely unsatisfactory.