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Jul 1, 2010
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I took a short trip to Chicago a few days ago. I've saw and experienced a lot of things.
Here are my positive and negative impressions of Chicago.

Chicago, in comparison with Toronto,
-had a better and neater city planning than Toronto.It had a very nice riverside walk, an urban park in the great location, and nicely drawn N-S, W-E roads and subway lines stretches out to its suburbs.
Chicago looked to me like a very "handsome" guy. :)
-Chicago had a lot more impressive historic architecture and skyscrapers than Toronto. not only by the number or size, but it was truly a great city of art and architecture.
-The city had several levels(?) in the city like the street level, high way level, and the river level. This gave me the impression of massiveness.
-There was a very convenient subway line connects the city and O'hair int'l airport. It saved me a lot of time and unnecessary effort.
-Chicago River ruining through the heart of the city and skyscrapers nicely aligned along the river line were very nice.

-However Chicago was a bad place when it comes to the safety. I was told not to even walk around after sunset in many parts of the city.
-One interesting thing was there were many *black people begging at almost every corner of their downtown. There was no Asian beggars, no white beggars, no Hispanic or brown beggars.. but millions of black beggars.
-It seemed that the south side of the city is regarded as an unsafe area, and the north side is a safe one. I was shocked by that extreme segregation between black and white people there.
-I always thought TTC was a horrible transportation when it comes to the quality of service and facilities comparing to where I used to live, but Chicago's was even worse.
-People in Chicago were relatively unkind. e.g. they ignored me with about 5 times higher chance than Torontonians when I was asking for directions.

Yes, these were my impressions of Chicago when I was visiting the city.
Now, here are a few pictures that I took.








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Chicago is an amazing city! I try to visit every summer. One thing i love most about Chicago is the condo-less beach and waterfront area nothing better than going for a morning stroll on the waterfront gazing up at the skyline, i stay in the gold coast area when i visit, The Pedways (tunnels ) under the busy Lake Shore Drive makes it easy access the waterfront area. I agree with you about South Chicago, it's a pretty rough side of town and being so close to Gary Indiana a city which is nearly 100% ghetto doesn't help South Chicago out much.
PUTOTO, Very nice pictures and tour.

Chicago has a lot going for it, although the cons sound horrible.

I'll add: the Shedd Aquarium - Toronto needs something like this.

Navy Pier - their version of Ontario Place, Harbourfront and Queen's Quay Terminal put together but not as remote from the downtown.

Last time I was there in 2007 the subway to O'Hare was running very slow - about 20km an hour on the elevated sections. The trip from the city center to O'Hare took 45 minutes. The reason for this was that the elevated parts of the line were in poor shape - there was signage to this effect - and I suppose they didn't want the cars to shake things to pieces. I wonder if improvements have been made.
If anyone feels comfortable using Priceline, you can usually get the Hyatt (the hotel Obama stayed in on Election night) which is on Michigan Ave right between the Navy Pier and Millenium Park for $60/night. Huge steal and it's a perfect place to enjoy Chicago.
Chi-Town is fantastic, but altogether a different offering from TO...
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When at Chicago, don't go to the south side at night, that is I was told when I was there. But it is definitely a great city with lots of interesting places to visit as a tourist. I love to go back there if I have the time. Great pics by the way.
Architecturally it's my favorite downtown of any in the US- very impressive and imposing buildings. One of the differences with Toronto is the number of great vistas and open views pedestrains get, due in part to the Chicago river. However, if one ventures outside the core some parts quickly deteriorate and look very slummy, and yes downright dangerous compared to the poorer areas of Toronto and larger European cities.

Note: not sure it was necessary to specifically point out the race of the homeless beggars you encountered?? Nice pics though.