For those who don't know, Chicago is considered by many to be the most bicycle-friendly city in the United States: among other amenities, the city provides over 150 miles of exclusive paths and lanes for bicyclists, over 10,000 sidewalk bike racks (and counting), special incentives for companies who encourage their employees to bicycle to work, not to mention bike racks on the fronts of every city bus, as well as hundreds of bicycling events per year sponsored and paid for by the government. (Those who are interested in learning more can visit the city's official bicycling website, ChicagoBikes.org.)
I myself have been an enthusiastic Chicago bicyclist since 2005, and in fact use my bike for almost every inner-city trip I now make (weather permitting, of course). So in 2007, when Google introduced the ability to create sophisticated online maps within both their 2D Maps software and 3D Earth, I thought it would be fun to highlight some of the routes I use in the city on a regular basis, as well as taking photos and videos and pointing out historically important sites along the way. A master city map showing all the routes I've plotted out can be seen below, with text descriptions following; if the description contains a link, that means the map is now finished and online. Once over at the 2D Google map, then, you can click on the "KML" link in that page's upper-right corner, to download the 3D file for Google Earth (the option I highly recommend).
By the way, if you find any errors in these maps, do make sure to drop me a line at ilikejason [at] gmail.com; I'll make sure to correct it, as well as give you a public thank-you here at my site. All maps start in the Uptown/Buena Park neighborhood in which I live (hence the title of this series). Enjoy!

1) Lakefront Path: Lincoln Park North. Part 1 of my five-part guide to Chicago's 18-mile uninterrupted lakefront bicycle path. This map details the northern half of the seven-mile Lincoln Park, one of the oldest and largest urban parks in the nation, built in stages from literally the 1860s to 1960s.
2) Lakefront Path: Lincoln Park South. Part 2 of my lakefront guide, this time detailing the older southern half of Lincoln Park, the location of its more famous landmarks including the zoo.
3) Lakefront Path: Lincoln Park to the Loop. Part 3 of my lakefront guide, this time detailing the sometimes tricky turns between the southern tip of Lincoln Park (at North Avenue) and the northern tip of the Loop (at Randolph Street, which is also the northern tip of Millennium Park).
4) Lakefront Path: The Loop to Hyde Park. Part 4 of my lakefront guide, this time detailing the newest section of the path, from the Museum Campus in the South Loop to Promontory Point at the northern tip of Hyde Park.
5) Lakefront Path: Hyde Park to the South Shore. Part 5 of my lakefront guide, this time detailing the Hyde Park neighborhood, Jackson Park (site of the Museum of Science and Industry), and the South Shore Cultural Center.
5B (blue): The Neighborhood Parks of the Chicago River. Part 1 of a related three-part guide to the hundreds of small neighborhood parks on Chicago's northside. Here, a detailed look at the five miles of interconnected greenways spanning the Chicago River from Belmont to Peterson, a century-old plan originally conceived by the German and Swedish families who lived in this area during the Victorian Age.
6) The Pre-City Parks of the Far North. Part 2 of my three-part guide to the northside's hundreds of neighborhood parks. This map looks at the large parks on the far north edge of the city, most created long before this area was officially a part of Chicago, containing such surprising elements as lagoons, sledding, prairie wild-growth experiments, and an official city zoo that hardly anyone even realizes exists.
7) The Neighborhood Mini-Parks of the Northside. Part 3 of my three-part guide to the northside's hundreds of neighborhood parks. Here, a day-long trip that meanders among the dozens and dozens of tiny "mini-parks" and designated playlots on the northside -- some created by activist locals in the Victorian Age (long before the city provided official parks), some created out of vacant slum lots in the 1960s and '70s using federal aid. Plus detailed instructions for joining up with the lakefront path at its northern terminus.
8) Burnham's Boulevards and the West Side Parks. As part of the "City Beautiful" movement in the early 1900s, it was recommended by legendary city planner Daniel Burnham that Chicago create a "green ring" of connected extra-wide boulevards through what at the time was the city's most congested working-class neighborhoods, creating not just a city-spanning avenue for pedestrians and bicycles but also a swath of nature within what at the time was a very polluted urban area. This was then combined with a series of grand public parks on the city's west side, some of the first urban parks on the planet to be landscaped in a unstructured, wild-growth manner. My map covers the northern half of this still-existing green network, starting at Diversey Boulevard near the lakefront and ending at the Garfield Park Conservatory. (The brown part of the route shown above, then, is technically the southern half of this boulevard/park system, but is not recommended: it not only passes through several high-crime areas, but the parks along the way are badly maintained, part of the pervasive inequality in city resources between the north and south halves of Chicago that has existed since the city's founding.)
9) Historic Neighborhoods of the Near South. Did you know that there are half a dozen nationally important historic neighborhoods all butting against each other in Chicago's Near South Side? There are! Here, a map detailing them all, including the IIT campus (home of a dozen architecturally famous buildings), Bronzeville (Chicago's first rich black neighborhood), Prairie Avenue (Chicago's first rich white neighborhood), the Museum Campus, Chinatown, Printers Row and the South Loop.
10) The Bike-Friendly Southside. A look at the bike-friendly areas of what is sometimes a sketchy Chicago southside. The route starts at the Douglas Tomb on 35th Street, traveling south down Drexel Boulevard to Washington Park (proposed site of Chicago's possible 2016 Olympics bid), then through the University of Chicago campus to Jackson Park (home of the Museum of Science and Industry), then across the old World's Fair Midway to the 55th Street el station.
11) The commuter bike lanes of the northside. The city is constantly encouraging downtown workers who live on the northside to actually bicycle to their offices in the morning instead of driving or taking the bus; in that regard, they've created a series of clearly-marked, extra-wide urban bike lanes among a multitude of streets from Rogers Park to the Loop, including nearly the entire lengths of Clark, Southport, Halsted, Elston, Lincoln Avenue and more. Here, a collective look at all these inner-city paths, along with tips for making these rides as safe as possible.
12) Chicago's Downtown. The four neighborhoods making up Chicago's "downtown" district -- the Loop, the South Loop, River North and River West.

