While the Chicago flag is a bit inside baseball (and probably included solely as a sop to the Chicago political establishment, who intend to own the Olympics as thoroughly as they own everything else that ever came out of Chicago politics), I do think that incorporating a bit of the local flair into the logo is a good design goal. I like Madrid's logo, don't get me wrong, but couldn't it be San Fransisco's logo, or London's logo, or Moscow's logo, etc, without modification?
I kind of like Tokyo's -- the ribbon is togetherness but the design is distinctly Japanese. I expect the prominent inclusion of the hinomaru (the red disk in the center of the Japanese flag) probably will get a raised eyebrow or two from some quarters, but the Olympics is not exactly a celebration of anti-nationalism now is it.
I agree that the "M" is a little understated. However, I personally don't feel it's so important that Madrid "owns" the logo at this stage - it'll come to identify with the city eventually if they win the bid and the logo enters the public consciousness.
Alternate logo and real-life usage of the Madrid logo at the designer's site: http://www.behance.net/Gallery/Madrid-2016/182876
Heh... Check out the 1964 Tokyo Olympics logo: http://www.sportslogos.net/league.php?id=27
If it doesn't have all three of red, white, and blue or both of stars and stripes, the designer almost certainly wasn't going for an American flag. For example, the overwhelming majority of Americans would not connect a white star and a blue star paired together as recognizably American.
American flag iconography also tends to use wavy lines, for the "flag fluttering in the breeze" effect. Additionally, it overwhelmingly features the flag oriented horizontally with the blue bits in the top left.
For a good example of modern American flag iconography, see the Obama O logo (which is, incidentally, probably the best logo I have ever seen in politics or otherwise, and I say that as a Republican). You don't remember McCain's campaign logo (that's a statement, not a question, nobody remembers it) but it had a Navy Star rather than a flag at its centerpiece.
Sorry, I get a kick out of this stuff. Tangent over.
http://en.wikipedia.org/wiki/Usa_flag#Historical_progression...
The US Navy star design: http://www.flickr.com/photos/stevestr/434646324/in/set-72157...
The Chicago 2016 logo blends the colors of the five Olympic rings surrounding the city’s six-pointed star, evoking serene blue lakefront, vibrant green landscape and fiery skyline. It also evokes Chicago’s Games concept—to host compact Olympic Games celebrated in the center of the city, along the lakefront and in the city’s parks.
Plus the symbolism of the handprint is much more universal than any star or ribbon can be.