13 Best Places to Eat & Drink in the South Loop

There are blues sets and jam sessions (be warned: some have $20 covers) most nights of the week, and free, all-ages acoustic shows for lunch and dinner. Come on a good night and you might even see American blues guitarist and singer George “Buddy” Guy overseeing the whole operation from a seat at the bar. While its known for the music, po-boys, gumbo, and jambalaya are available until midnight.

So, sure, some might think of the South Loop as a stopover on the way to some of Chicago’s best museums, but those people are simply uninformed. Between dives, live music, fine dining, and taproom tastings, this ‘hood could very well be considered an attraction in and of itself. So here are the 13 best places to eat and drink just South of Downtown.

With some of Chicago’s best breakfast sandwiches and Bloody Marys, plus its close proximity to Soldier Field, this old-school deli is a prime pre-Bears game spot. The pastrami is super tender and the milkshakes are so thick and creamy you’ll need to tackle ‘em with a spoon.

No matter if you’re here to sip matcha lattes while pretending to work on your MacBook or to day drink local beers — like South Loop Brewing’s Good Ryes Wear Black — you’ll forget you’re Downtown out on the huge patio. The cafe’s regular hours are 7am to 6pm, but it’s known to stay open late if people are still hanging.

One of the oldest bars (in one form or another) in the city, according to its website, this low-key neighborhood pub is a Printer’s Row mainstay for bookish types who like decent craft beers and their dogs.

Break brick-oven flatbread together at this airy, upscale, Lebanese-inspired spot from the owners of South Loop Market, then share small plates of bacon-wrapped dates stuffed with goat cheese and pecans, rosemary-infused baba ghanoush, and the duck shawarma platter with saffron basmati rice and grilled vegetables.

From green tea waffles with lemon-ginger chantilly cream and ground pistachios, to red velvet waffles with cream cheese icing and cherry compote, to braised short rib-topped cheddar waffles, boring old Belgians can be damned.

The taproom has 14 rotating small-batch drafts, plenty of communal tables next to floor-to-ceiling windows, and a bunch of board games (Battleship! Heads Up!), plus you can bring your own food/dog.

Grilled whole chicken served just right — fast, cheap, and tender. Choose from white or dark meat, or just get the whole dang bird.

So although the Cubano sandwich, with its citrus-garlic marinade, is most definitely one of the best in the city, you’d be remiss to not also try the more substantial chivito sandwich piled high with steak, ham, bacon, and a fried egg.

The pork belly sliders with apple slaw alone are worth the trip, but if you insist on options there are plenty: ramen, sushi, and Mom’s Ginger Garlic Fried Chicken. We’re not clear whose mom these chicken wings belong to, but she should be celebrated. Pair it all with a house-made mango fruit soda or a cucumber-mint sake slushie, and then head out to the massive patio.

There are two distinct rooms for live shows at this multi-stage music venue/record store/restaurant — Reggies’ Music Joint and Reggies’ Rock Club — but the biggest attractions are the rooftop bar’s basketball hoop and pool table. So that, plus the 30 specialty bottles, 24 drafts, and 17 flat-screens showing games and performances, means you don’t actually have to be into live music to hang here.

One of Chicago’s best value Michelin-starred restaurants, this lil’ hideaway delivers standout fancy fare like Wagyu beef tri-tip with oxtail prune consommé and Tasmanian ocean trout. But if you don’t feel like footing that bill, head to the bar for the double-pattied burger topped with double-cream Gouda and house-made applewood bacon.