I found this website which describes the Municipal Flag of Chicago. It is not unusual for a city to have its own flag, usually you only see them at municipal buildings (city hall), but in Chicago the flag is much more prevelant. Follow this link for more info.
Just thought maybe you would like to known what everything on the Chicago flag represents. The 2 blue stripes are for the 2 bodies of water in the area, lake Michigan and the Chicago River. The 3 white stripes are for the three areas of the city where people live, the north, south, and west side. Then there are 4 stars. 1 star represents, fort Dearborn, another represents The Great Chicago Fire, and the last 2 represent both Both of the World Fairs Chicago hosted.
Same as it is today with one less star.
The Chicago rivers
Each country has its own flag.
one of them represents the Chicago fire and another is the worlds fair in Chicago
Yes, it has a flag.
No he is not Jewish the stars on his trunks are the Chicago stars shown on the Chicago flag.
Flag is used for your own convenience. If you flag it, it's like bookmarking it. It can mean to go back to it, to remember it, or to flag it as inappropriate. Either way, you use it to your own will.
Wave the Flag
Yes, the Commonwealth Games have their own flag
Canada has had it's own flag since 1965. Hope this helps!