I'm in Chicago 
again for my yearly conference, and while I spent some time this morning on the recumbent in the hotel health club, I don't think I'll be getting many street miles in during my visit.  It's a little cold, a little wet, and a little crowded for my tastes.
However, I did ride in Chicago once.  Maybe in 1999 or 2000, I took part in the Boulevard Tour.  
This year's was held in September, but my foggy memory puts it in the spring - maybe May.  Regardless, we started at the U of C campus at the site of the 1930 something World's Fair and rode up through Chinatown, the Loop, the Puerto Rican district (there was a big neon PR flag installed over the street in the business district), and then back south on a path slightly west of downtown.  I think it was around 45 miles.
I hadn't been in a big city ride before, and I just loved the idea of thousands of riders taking over the LaSalle banking district - even on a Sunday.  The tall buildings, which are a little intimidating and are difficult to see from a car, were resplendently visible, and the normally busy streets offered lanes for the taking.  There was a tandem bike pulling a trailer that contained a drummer, a guitarist, his amp, and a generator.  The two riders were working hard to keep the music traveling.  (The duo sounded horrible, but I still loved it!)  The route was barely marked, and the SAG stops were undersized and backed up - what a great day!
I wish I had photos to share, but I had a camera accident at the beginning of the ride.  My Kodak camera was bumped while in the pannier, causing the lens mechanism to attempt to engage.  I had things packed tight, so the plastic gears stripped instead.  It was fixed about $250 later.  (One would never think of fixing a digital camera today.  The price of repairs is too close to the price of a new one - with better features!)
I was riding with a co-worker who pushed very hard through most of the ride, but bonked about 5 miles from the end.  He was cursing himself and getting generally upset, while I was happy just to be finishing.  We rode in the Wabash River Century later that year, and he did the same thing on that route - stopping every five minutes of the last stretch to restate how much of an idiot he was for not pacing himself or for not being strong enough.  I didn't ride with him after that.
While I'm out sightseeing/shopping this afternoon, I'll look for messengers or commuters.  And I'll be a little jealous.