I worked on this illustration off and on for 4 months. If I had to describe my "style", this is the best example I can provide. This particular illustration is a graphically styled re-imagination of famous Chicago landmarks and icons.
1. Fireworks display on July 3rd.
2. Trump International Hotel and Tower Chicago
3. Bleacher bums at Wrigley Field. The ivy is part of the outfield wall around Wrigley. The W on shirt refers to the flag they hang after a Chicago Cubs win. The girl is wearing a shirt that says AC0063100. The numbers refer to the last time the Cubs won the division championship, National League pennant, and the World Series. This sign is on a rooftop across Sheffield Avenue. (The poster was completed in 2009.)
4. Smurfit-Stone Building

5. Chicago Cubs player
6. A number from the Wrigley Field manual scoreboard.
7. Glasses from iconic Chicago Cubs broadcaster, Harry Caray.
8. Curse of the Billy Goat. A curse was supposedly put on the Cubs when the owner of the Billy Goat Tavern was asked to leave a World Series because his goat was bothering fans. The Cubs have not been to the World Series since.
9. Deep dish pizza. The names on the side refer to famous deep dish pizza places, Gino's East and Lou Malnati's.
10. People playing volleyball on North Avenue beach.
11. Buckingham Fountain
12. Cloud Gate, better known as The Bean.
13. The Chicago Tribune.
14. A boat sailing on Lake Michigan. Venetian refers to the Venetian Night Festival held in August.
15. Runner and biker on Lake Shore path. The sign is the logo for McCormick Place.
16. Taste of Chicago booth. A food and entertainment festival held in Chicago around July 4th every year. The sign refers to famous food and immigrants in Chicago. "Cheezeborger! Cheezeborger!" refers to the Billy Goat Tavern. The immigrants referenced on the sign and the booth are Chinese, Mexicans, Greeks, and the Polish.
17. The guy at the booth has a Chicago hot dog in front of him.
18. The pinwheels are icons of Comiskey Park and U.S. Cellular Field. "He Gone..." is what broadcaster Hawk Harrelson says when someone strikes out.
19. Chicago White Sox player. The 2005 on his bat refers to their last World Series win.
20. Blue Angels. They perform during the Air and Water Show in August.
21. Willis Tower, formerly known as Sears Tower.
22. The mad scientist refers to the Museum of Science and Industry.
23. State Street bridge. One of the more famous streets in Chicago.
24. The Picasso outside The Daley Center
25. An architectural tour boat travelling down the Chicago River.
26. The dolphin refers to the Shedd Aquarium.
27. Chicago Blackhawks player
28. Marina City
29. Aon Center
30. Lake Point Tower

31. The "L" or elevated train. The destination of the train is in blue on the front, O'hare Airport.
32. A blue devil for DePaul University.
33. Lion sculpture outside of the Art Institute
34. Famous gangster Al Capone
35. The guy making fun of Al Capone is wearing a logo of The Second City, a famous improvisational comedy venue.
36. Crown Fountain at Millennium Park
37. Chicago Bears player. The "Da" on his helmet refers to the way people say "The Bears" with a Chicago accent, "Da Bears". The column he is holding refers to Soldier Field. The 85 on the end of the column refers to the only time they won the Super Bowl.
38. Oprah Winfrey
39. Ferris Wheel at Navy Pier
40. Wrigley Building

41. Michael Jordan statue outside of the United Center, home of the Chicago Bulls. The numbers on the side refer to the six times they won the NBA Championship.
42. Lower Wacker. Famous shortcut underneath parts of downtown.
43. Potholes. Famous road hazard.
44. John Hancock Building
45. Street sign for famous expressway, Dan Ryan, and destination, The Loop.
46. Three guys playing the blues. The Buddy coming out of the trumpet refers to a famous place to hear the blues, Buddy Guy's Legends.
47. Stores along the Magnificent Mile. A large retail area along the most famous street in Chicago, Michigan Avenue.
48. Shoppers carrying bags with the zip code for the Merchandise Mart.
49. Chicago Water Tower. One of the few buildings to survive the Great Chicago Fire of 1871. The cow at the bottom is Mrs. O'Leary's cow, the supposed cause of the fire.
50. Maxwell Street Market sculpture. Open air flea market that began on Maxwell Street in the early 1900s.
51. Chicago Trolley.
52. The dinosaur skeleton refers to the Field Museum.
53. Soon to be former mayor, Richard Daley. The wind coming from his mouth refers to the nickname for Chicago, The Windy City.
54. The Chicago sign is replicated after the sign for Navy Pier.
55. Famous residents Barack and Michelle Obama. President Obama has a handkerchief that says U of C which refers to the University of Chicago. The First Lady is holding a Chicago flag.
56. Ulysses Grant sculpture in Lincoln Park.
57. The guy with the telescope refers to the Adler Planetarium.