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