The view of the Chicago Skyline from the Adler Planetarium, which is part of Chicago’s museum campus, along with the Field Museum of Natural History, the Shedd Aquarium, and Solider Field, home of the Chicago Bears.  To the left of the skyline is the 110-Story Sears Tower, America’s Tallest Building.

Population 

2005 City Population: 2,842,518 (3rd Largest US City)
2005 Metro Population: 9,661,840 (3rd Largest US Metro)

In comparison - Jacksonville, Florida
2005 city population: 782,623 (13th largest US city)
2005 metro population: 1,248,371 (42nd largest US metro) 

City Description (from AViewOnCities.com)
Louis Jolliet, a Canadian explorer and the French-born Jesuit Jacques Marquette were the first Europeans to discover the Chicago area in 1673 with the help of local Indians.

The first permanent settlement was founded in 1781 by Jean Baptiste Point du Sable, an African American from Santo Domingo. The location at the mouth of the Chicago River was chosen for its strategic value for a trading post as the river connected the Lake with the Mississippi river. Later the area at the mouth of the Chicago River was occupied by a military base, Fort Dearborn. The Fort was regularly attacked by Native Americans, until Chief Black Hawk was defeated in 1832. One year later, Chicago was officially incorporated as a town and four years later, when the population reached 4170, as a city. Its name was derived from the native indian's word describing the area.

With the arrival of the railroads, the city of Chicago really started to boom reaching a population of 300,000 in 1870. One year later, disaster struck with the Great Chicago Fire laying the city in ashes. The fire destroyed about 17450 buildings, but the Chicagoans quickly started to rebuild the city. Just 6 weeks after the fire, construction of more than 300 buildings had already begun. And in 1893 Chicago had recovered well enough to host the 1893 World Columbian Exposition, commemorating the discovery by Columbus of America 400 years ago.

Learning from Chicago
Needless to say, Chicago is a city that Jacksonville probably will never be.  Chicago’s architecture is incredible, its downtown is vibrant, and it boasts Michigan Avenue, known by locals as the Magnificent Mile, and the Windy City's Answer to Paris' Champs-Élysées and New York's Fifth Avenue.

One may look at Chicago and say, “Jacksonville will never look like this”.  While that is true, there are some aspects of big city life that can be applied to Jacksonville.

Chicago is on Lake Michigan, and extends out to the North, West, and South from there.  The epicenter of Downtown Chicago is known as the Loop, named for the elevated train “L” lines that encircle the core of the downtown.

Chicago is a city of great neighborhoods, a city that doesn’t forget about the historical residential and commercial areas of its urban core.  A great example of that is Wrigleyville, the area surrounding the Chicago Cubs’ famous stadium, Wrigley Field.   Besides being home to the Cubs, the area is home to expensive residences, cool shops, and a great nightlife district (what a concept).

Positives of Chicago’s Core:

1. Transit (all kinds)
If you want to ditch the car, you can truly do it in Chicago.  Chicago is known for the L (Elevated Train), which serves Chicago with 10 lines running frequent enough that you don't need to check schedules before you leave the house.  Chicago also boasts an excellent bus system (and stations with shelters and full system maps), and a commuter rail system (Metra) that spans three states (no kidding).

2. Signage
No matter what the signage was for, it was very good.  Need to know where you are? Go the wayfinding signs on the sidewalk.  Need to Park?  They are a fan of the giant “P”.  Need to see the entire Chicago Bus and Rail System Map?  Just go to ANY rail OR bus station.

3. Parking
In a city with all sorts of transit options, who needs a car?  However, if you chose to drive, finding parking was not a problem.  Parking was very clearly marked and easy to find (though very expensive).  Finally, Chicago has recognized the need for smart meters - they are converting right now.

4. Public Spaces
If we want to create "flex space" take a look at the Grant Park area, Chicago's "Front Yard" on Lake Michigan.  Its newest addition is Millennium Park, which opened in 2004 above rail yards and a surface parking lot.  While this project is a fantastic addition to the Grant Park area, it was not without it's problems.  The park opened four years late (hence the name "Millennium") and $325 million over budget. Note to Mayor Peyton - Just make the courthouse a park, and all will be forgiven.  For more information and pictures of Millennium Park, visit http://www.millenniumpark.org

Negatives of Chicago

1. Loop at Night
Chicago is known for the loop, but you can find yourself wondering where all the people are after five (not nearly as bad as Jacksonville, however).  Other than State Street, which is a “poor-mans” Michigan Avenue, the streets of the Loop are quiet, and without activity.  Most of the buildings in the loop are either governmental or financial, with few night-time things to do

2. Getting Around during Special Events (sound familiar)
These people must have gone to the Jacksonville school of special event traffic management.  Try hailing a cab or catching a bus anywhere near Solider Field before a Bears game – forget it, the streets are blocked off.  However, they aren’t quite as bad as Jacksonville; the only streets that were blocked were around the stadium, not the entire downtown area.

Chicago Photo Tour

Chicago does a great job with adaptive reuse.  This hotel from the 1920’s was reopened in the late 90’s after extensive renovation.  At the foot of the building, what else? – retail.  In this case, a Brooks Brothers.

Chicago's Michigan Avenue is lined with shops of all kinds, from moderately priced to outrageous.  The building above is a perfect example of mixed use, with four major retailers on Michigan, with offices above the street level.  By the way, the building on the left of the picture is a 7 story Saks Fifth Avenue.

This is from an area called North Bridge, just north of the loop, and east of Michigan Avenue.  This area is known for it's restaurants - it has some of the more touristy restaurants, like ESPN Zone, Weber Grille, and Rock Bottom Brewery (above).  Notice the wayfinding signage at the intersection to be sure you're never lost.

Outside of the tourist-friendly areas, Chicago still gets it right. Chicago’s sidewalks are wide enough for two people to pass without running into each other (the ones in the high traffic pedestrian areas are super-wide).  Notice the grating at the foot of the tree?  This is done so that the tree takes up only as much sidewalk as absolutely needed.  This is something that should be considered on Laura St in Jacksonville; remove the planters and put this type of grating around the trees.  Finally, look down the sidewalk, and notice the pedestrian friendly signs for the storefronts.

This is a great picture, because this one block highlights at least four things that Jacksonville can’t figure out how to do, but are tremendous downtown assets (however the bus only lane is not one of them):
1. Notice the pedestrian tunnel on the right – when a building is under construction, you don’t have to block the entire sidewalk.
2. Past the train station at the intersection, check out the illuminated “P” sign with the huge “SELF PARK” banner. 
3. On the right, notice both the awning with signage and the banner sign hanging off of the side of the building.  Find me some examples of that in Downtown Jacksonville.
4. Notice on the sidewalk, they don’t put trees and plants in if there is not room for them.  In Jacksonville, we seem to have a “form over function” concept of sidewalks with the plants and bricks.  Notice how many bricks there are in the sidewalk, and how many trees there are.  However, people seem to have enough room to walk, don’t they?

JTA, pay attention here.  Look at the bus stop sign - each sign has the route number and name, but also a quick blurb about where the route goes, and when it runs.  Plus, nearly every stop had a shelter with a route map (see example below).

Notice in the bus shelter, the map of the entire system, with an inset of the area you are in.  That red arrow and dot on the inset map? A “You Are Here” marker!  By the way, the Chicago Transit Authority is okay with advertisements on the sides of their shelters.  During the entire visit to Chicago, I didn’t hear anyone say, “You know, this ad is so tacky that I’d rather stand in the rain than be under this shelter.”  For the record, all of the shelters were very clean, and the ads were done very professionally.  In the background is some friendly tailgater's (the Bears-Packers game was that evening).

Staying on the mass transit note, Chicago has a trolley system that runs through their downtown, just like Jacksonville.  Unlike Jacksonville, I know it’s free, I know where it goes, and the sign didn’t have any obvious typos.  Compare:

Chicago:

Jacksonville (look carefully at the route times):

Conclusion
In this piece, we could have mentioned a lot more things that Chicago has that Jacksonville doesn't, but it would have taken a month to read.  The fact is, Chicago is America's third largest city, and Jacksonville will never be that big.  The point is, most of the things discussed would be relatively cheap to implement, and are examples of how to make Jacksonville more pedestrian friendly.