Watch their chats about concerts at Wrigley to where Illinois ranks on the happiest state in America.
They also caught up with Rock and Roll Hall-of-Fame drummer and TV personality Max Weinberg about his legendary career and recent shows coming to Chicago.
Plus, Ryan puts Weinberg through The Friday 5. Find out who Weinberg thinks wears tighter pants, Bruce Springsteen or Kim Kardashian!
If you're a fan, you can catch Weinberg this weekend.
Sunday Sept. 19 at 7:30 p.m.
Ticket Info: www.ravinia.org
Thursday Sept. 23 at 8 p.m. & 10:30 p.m.
Ticket Info: www.citywinery.com
RELATED: Roz Varon's Weekender Report
Spend or Save?
The weekend means new movies in theatres and new shows to stream. Our film critic, Richard Roeper, shares what to watch and what to skip.
"Cry Macho" - SAVE
A has-been rodeo star and horse breeder heads to Mexico in hopes of rescuing his ex-boss's son. Clint Eastwood stars and directs "Cry Macho."
"Chicago Party Aunt" - SPEND
Chicagoans love the Chicago Party Aunt on Twitter, but she's morphed into cartoon form in a new Netflix series.
"Prisoners of the Ghostland" - SAVE
Nicholas Cage is sent to rescue the governor's adopted granddaughter in this Western action film.
"Live at Mr. Kelly's" - SPEND
A PBS documentary about the legendary Mr. Kelly's nightclub on Rush Street.
Watch "Windy City Weekend" each Friday at 11:30 a.m., following ABC 7's EYEWITNESS NEWS at 11 a.m.