Taste quest Park Manor/Chatham

A South Side gem, 75th Street is the dividing line for the Chatham (to the south) and the Park Manor (to the north) neighborhoods. The strip offers a variety of the expected Caribbean and soul food spots, but there’s also a peerless vegan restaurant that draws diners from across the city. We’re limiting ourselves to a mile stretch, and that still leaves more than enough for a weekend’s worth of destinations to hit. Start a block from the Dan Ryan and work your way east until sated. Stop. Rest. Repeat.

First, a few words on attire: If you expect entrance to the 1 Fifty Yard Line Bar and Grille(69 E 75th St, 773-846-0005) after 9pm, look sharp—no ball caps, jeans or sneakers. The Fifty Yard Line is both a sleek steppin’ club and a sophisticated sports bar, and the club owner says the dress code keeps out the “riffraff.” For dinner beforehand, try 2 Soul Vegetarian(205 E 75th St, 773-224-0104), an iconic restaurant run by African Hebrew Israelites. It’s vegan (attention hard-core vegans: There are a few dishes that include honey), alcohol-free and based on the tenets of the “divine diet” (nuts, fruits, vegetables). That said, Soul Veg is most popular for its mock meat: This is a restaurant devoted to the glories of textured wheat gluten, and the tables are crowded with vegetarians eating barbecue seitan sandwiches. Soul Veg may be the least subtle and most flavorful vegetarian restaurant in Chicago.

New Apartment Lounge

What else is there to say about3 Lem’s (311 E 75th St, 773-994-2428), the great barbecue mecca? Well, the sparkling neon signage is endlessly charming, and we’ve always been impressed by how many staff members fit in that tiny space between the Plexiglas window at the counter and the smoker. Oh, and the barbecue? When just off the smoker, it is among the city’s best, gloriously meaty and full-body–staining. At their best, Lem’s rib tips can take you out of your car—that’s where you’ll be eating, since the restaurant’s takeout only—and into a closer communion between man and pig.

A block east, the newish 4 Black Wok(405 E 75th St, 773-874-4965) brings the Flat Top Grill dance to 75th Street: You put your protein in, you put your sauce in, you put your starch and veggies in and you—well, the cooks—shake it all about. Next door, 5 Harold’s Chicken Shack #24(407 E 75th St, 773-488-9533) is a favorite of the Harold’s cognoscenti (and there is a Harold’s cognoscenti), turning out reliably fantastic wings.

Daddy O’s Jerk Pit

Soul-food institution6 Army and Lou’s(422 E 75th St, 773-483-3100) has a serious customer pedigree: A favorite of former Mayor Harold Washington, it also attracted lesser-known folks like Martin Luther King and Muhammad Ali and is known for being staffed by the nicest, most polite waitresses around. A fixture since 1945, Army and Lou’s serves chitterlings and sweet-potato pie in portion sizes that will stick to your ribs. You’re not just getting dinner here; you’re getting tomorrow’s lunch.

We’d strongly recommend taking in 75th Street on a Tuesday—that’s when Von Freeman, Chicago’s legendary, bronze-plated tenor saxophonist takes occupancy of the 7 New Apartment Lounge(504 E 75th St, 773-483-7728). The cover is nada, saving you dough to buy a few drinks to sip at the curved bar under the glow of Christmas lights. It helps to have a seat: Vonski, as Freeman is nicknamed, is a raconteur whose stories sometimes go on as long as his solos. Midway through, Freeman invites young musicians to sit in with the band, and on a normal night, the line of aspirants—instrument cases in hand—snakes around the club.

For a dose of tropical tastes, 8 Café Trinidad(557 E 75th St, 773-846-8081) is a casual place that’s so family-friendly that random small children may stop by your table. (Okay, the boy ran away after we talked to him.) Trinidadian food is a mélange of Indian, African, European, Chinese and indigenous traditions. In practice, that means roti sandwiches (Indian bread wrapped around fillings like goat, shrimp or cabbage and greens), curry chicken, and callaloo a side dish that’s made here with spinach and okra. The requisite jerk and soul-food options are available, too, and the housemade ginger beer is racy and seriously strong. (That said, it isn’t booze and there’s no alcohol, but you’re welcome to bring your own. The table next to ours popped a bottle of bubbly.)

Café Trinidad

Photo: Martha Williams

Another Caribbean favorite,9 Daddy O’s Jerk Pit(7518 S Cottage Grove Ave, 773-651-7355) emits spicy smoke aromas that waft up to 75th Street. This Jamaican spot has more Bob Marley posters than a college dorm, as well as a smoker that takes up the restaurant’s front half. The jerk chicken is excellent and spiced with a sure hand. Deeply flavored oxtails fall apart like the Bush presidency, giving the chicken a run for its money. To avoid indecision, bring company.