Diamond Jim's Motor Cars is a used car dealer serving Chicago, IL and surrounding communities

Chicago, Illinois, known as the "Windy City," is an iconic metropolis in the Midwest, recognized for its stunning architecture, cutting-edge skyscrapers, and vibrant culinary scene. Nestled along the shores of Lake Michigan, it boasts an array of cultural attractions such as the Art Institute of Chicago, the Field Museum, and the bustling Navy Pier. Chicago is also renowned for its music legacy, being the birthplace of the blues and a pivotal hub for jazz and hip-hop. The city, exuding a cosmopolitan charm coupled with Midwestern warmth, offers a wealth of food, music, arts, and popular sports teams, with an energy that captures the pulse of America.


Find your next used car, truck or SUV at Diamond Jim's Motor Cars

Diamond Jim's Motor Cars is Chicago's destination for cars, trucks, and SUVs. We're located at 5265 South 27th Street, Greenfield, WI 53221.

  1. Head north on N LaSalle St toward Chicago Pedway System (446 ft)
  2. Turn left onto W Randolph St (0.7 mi)
  3. Turn right to merge onto I-90 W/I-94 W (7.6 mi)
  4. Keep right to continue on I-94 W, follow signs for Edens Expwy/Milwaukee (13.5 mi)
  5. Take the I-94 W exit toward Milwaukee
    Toll road
    (0.5 mi)
  6. Continue onto I-94 W
    Toll road
    (2.7 mi)
  7. Keep left to stay on I-94 W
    Toll road
    (21.7 mi)
  8. Keep left to stay on I-94 W
    Toll road
    Entering Wisconsin
    (17.1 mi)
  9. Take exit 337 toward Somers/Mount Pleasant (0.2 mi)
  10. Take the ramp to State Hwy 195 (0.1 mi)
  11. Turn right onto State Hwy 195 (1.8 mi)
  12. Turn left onto W 105th St (2.0 mi)
  13. Turn left onto WI-11 W/Wisconsin Trunk Hwy 11 W/Durand Ave (0.7 mi)
  14. Turn right onto International Dr (1.6 mi)
  15. Turn left onto WI-20 W (1.0 mi)
  16. Slight right onto the I-94 W/US-41 N ramp (0.4 mi)
  17. Merge onto I-41/I-94 W/US-41 (13.7 mi)
  18. Take exit 319 for College Ave (0.3 mi)
  19. Turn left onto County Rd ZZ/W College Ave (0.8 mi)
  20. Turn right onto WI-241 N/S 27th St (1.3 mi)
  21. Turn left onto W Upham Ave (200 ft)
  22. Turn right (108 ft)

Shop Diamond Jim's Motor Cars selection of used cars, trucks, and SUVs for sale near you

Shop All Inventory