Skip to content

Todd’s Random Chicago

An ever-evolving list of completely random (but important) things about Chicago.


  1. Quick note before we begin: We vouch for all restaurants listed.
  2. Scarface and the Untouchable: Al Capone, Eliot Ness, and the Battle for Chicago (a book by Max Allan Collins + A. Brad Schwartz)
  3. Little Goat Diner (a restaurant in West Loop)
  4. RPM on the Water (a private event space right on the Chicago River)
  5. Swift + Sons (a steakhouse in Fulton Market)
  6. Nico Osteria (a restaurant in Gold Coast)
  7. State + Lake Chicago Tavern (a gastropub in the Loop)
  8. Time Out Market Chicago (a food hall in West Loop)
  9. Odyssey Chicago River and Lake Cruises
  10. Metra (Chicagoland’s commuter rail service)
  11. Winter’s Jazz Club (a club in Streeterville)
  12. Atwood Restaurant (a restaurant in the Loop / Reliance Building)
  13. Benny’s Chop House (a restaurant in River North)
  14. Merchandise Mart (Wikipedia)
  15. City of the Century: The Epic of Chicago and the Making of America (a book by Donald L. Miller)
  16. The Gage (a restaurant next to Millennium Park/Loop)
  17. 12X5 (a Rolling Stones LP recorded in Chicago)
  18. Chriskindlmarket Chicago (a Christmas tradition in the Loop)
  19. Remington’s Chicago (a restaurant next to Millennium Park/Loop)
  20. The Kimpton Gray Chicago (a hotel in the Loop)
  21. Girl and the Goat (a restaurant in West Loop)
  22. The Hoxton Chicago (a boutique hotel in West Loop)
  23. RPM Steak (a steakhouse in River North)
  24. Quick reminder: If any of these links are dead, simply EMAIL me here.
  25. Chicago (a novel by David Mamet)
  26. Pizzeria Portofino (an Italian pizza joint in River North)
  27. Allegro Chicago (a hotel in the Loop)
  28. Gibsons Bar/Steakhouse (a steakhouse in Gold Coast)
  29. The Chicago Cubs: Story of a Curse (a book by Rich Cohen)
  30. Smith + Wollensky Chicago (a steakhouse under Marina City)
  31. Maple & Ash (a steakhouse in Gold Coast)
  32. Lincoln Park Zoo
  33. The Berghoff (a historic German restaurant in the Loop)
  34. Gibsons Italia (an Italian steakhouse in River West)
  35. Chicago Cubs
  36. Field Museum
  37. Art Deco Chicago: Designing Modern America (book edited by Robert Bruegmann)
  38. Museum of Science + Industry
  39. McCormick Place Convention Center
  40. Chicago Blackhawks
  41. Chicago Sun-Times
  42. Chicago Tribune
  43. Drake Hotel
  44. Buckingham Fountain (Wikipedia)
  45. The Art Institute of Chicago
  46. Terzo Piano (a restaurant INSIDE the Art Institute)
  47. Adler Planetarium
  48. The Chicago Theatre
  49. Shedd Aquarium
  50. Chicago Architecture Center
  51. Chicago Bears
  52. Il Porcellino (Italian restaurant in River North)
  53. Chicago Is… (promotional video from 1977)
  54. Chicago Transit Authority
  55. West Loop Veterinary Care
  56. United Center
  57. Al Capone (Wikipedia)
  58. The Chicago Flag
  59. The Chicago Marathon
  60. Northwestern University
  61. Mike Royko (Wikipedia)
  62. Palmer House Hotel
  63. Apple Michigan Avenue
  64. The Bob Newhart Show (opening sequence)
  65. This is Marina City, Part 1
  66. This is Marina City, Part 2
  67. Allen Robinson’s Within Reach Foundation
  68. Anything we should add? EMAIL me here!

You wake up in Chicago, pull back the curtain, and you KNOW where you are. You could be nowhere else. You are in a big, brash, muscular, broad shouldered motherfuckin’ city. A metropolis, completely non-neurotic, ever-moving, big hearted but cold blooded machine with millions of moving parts  — a beast that will, if disrespected or not taken seriously, roll over you without remorse.

ANTHONY BOURDAIN

My kind of town, Chicago is…

FRANK SINATRA