DoChatham-South Shore
Ok, this place is cool. A roller rink oozing with South Side character and home to not a few serious skaters who flaunt their moves to smooth R&B and old school. It has shown up a bit in pop culture, from the movies "Soul Food" and "Roll Bounce" to several nationally-aired music videos. If you are intimidated by the pros on the rink but want to check the place out, there are also arcade games and pool/ping-pong tables. It is open to different age groups at different times, so make sure to double-check the hours before coming here.
Tue 10AM-2PM (30+) 8PM-midnight (21+), Wed 5:30PM-8:30PM (families), Thu 8PM-midnight (30+), Fri 7PM-11PM, Sat noon-3PM (pre-teen) 7PM-11PM (teen) midnight-4AM (18+), Sun 5PM-9PM (30+) 9:30PM-1:30AM (18+)·$7, but varies
Big to-order burgers at a local favorite. Take-out only, and call ahead well in advance to avoid a long wait. The house specials are the Whammy Burger, which comes with a split Polish on top, and the T.a.B Special, topped with chili, cheese, bacon and egg. Beef or turkey.
Tue-Sat 11AM-7PM
A must for serious donut eaters as it is home to the legendary "Big Dat" — the mother of all donuts. In addition to quantity (i.e., size), the quality attracts devoted foodies from all over the Chicagoland area.
24 hours daily, except Sun 10PM-4AM·$0.25-2.50
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Old Avalon Theater
Built in 1927 as one of the South Side's most impressive movie palaces, done up in ornate Moorish Revival style, this theater was in operation well past the riots and up into the late 1970s. Since then, the theater has served as a church, and then a performance venue, before finally shuttering its doors in 2003. In 2008, however, the building caught a glimmer of new hope with a purchase by new owners hoping to turn the building into a new cultural venue. The idea hasn't quite taken hold yet, but there is reason to feel optimistic about this Chicago Landmark's long-term future. If you are not getting in for an event in the meantime (and believe it, the interior is in fabulous shape and incredibly beautiful), check out the cool mural on the side and ponder the building's incredible musical history; the venue's performers truly include every single world class blues, jazz, rhythm & blues, funk, and soul musician you can think of: John Coltrane, Count Basie, Nat King Cole, Sammy Davis Jr, Earth Wind & Fire, Duke Ellington, Ella Fitzgerald, the Supremes, Gladys Knight, the Isley Brothers, Billie Holiday, Isaac Hayes, B.B. King, Miles Davis, Stevie Wonder, Marvin Gaye, and so on.