15 South Side Restaurants That Are Worth the Drive

North siders and North Shore residents, Chicago doesn’t stop at Madison Street! There’s real life in the South Loop and beyond, and some great new restaurants that you really, really need to know about. To ease you into your migration south, I’ve thrown in a few yummy places near Symphony Center and Millennium Park as well. But it’s high time to bust out of your comfort zone and head south. Go now and thank me later.

Baby Steps: Just South of Madison


Just across from Millennium Park and the Art Institute of Chicago you’ll find this modern Italian gem, open for lunch, dinner and weekend brunch. Order any of the Salumi on offer ($11 for one, $28 for selection of four) and win the bonus: a side of delectably rich Parmesan fonduta, which you will smear on everything on the table, and possibly lick the bowl. The Black Peppercorn Rigatoni ($20) with spiced lamb ragout and caciocavallo cheese is a stand out. 18 S. Michigan Ave., Chicago, 312-578-0763


They’ve freshened the décor at this Loop favorite located in the Hotel Burnham at the corner of State and Washington. They serve every meal here (it is a hotel restaurant, after all) with a focus on the seasonal. Right now I’m loving the Pumpkin Gnocchi ($24) with rosemary-goat cheese cream, crispy kale and toasted walnuts — it’s like autumn in your mouth. And the insane Crispy Braised Bacon Sliders ($10) served on a soft brioche bun with herb aioli and apple/celery root/ kohlrabi slaw? Delish. 1 W. Washington St., Chicago, 312-368-1900

Chicago Athletic Hotel (Cindy’s, etc.)

Chef Christian Ragano (opening chef of Guildhall in Glencoe) is putting out some tasty food, but with this gorgeous view, is anyone even noticing? But go ahead, make a reservation, wait in line for the elevator (if you can get past the bouncer), and be transported. And while you’re there, splurge for the lovely Shellfish Platter ($72) and the Côte de Boeuf ($98) and split it with a few friends. Drink in the scene (crazy!) and be glad you scored a table. 12 S. Michigan Ave., Chicago, 312-792-3502 

Photo courtesy of Neil Burger.

Mercat a la Planxa

To my palate, this is the best and most inventive Spanish food in the city. Located in the Blackwood Hotel and presided over by Iron Chef and James Beard Award-winner José Garces, Mercat has it all: classic tapas, beautiful seafood cooked “a la planxa,” paella, even Roast Suckling Pig for the table (call 72 hours in advance to order). And the cocktails … Dios Mio! You’ll never want to leave. 638 S. Michigan Ave., Chicago, 312-765-0524

Seven Lions 

This gorgeous space, owned by famous sommelier and former “Check Please!” host Alpana Singh, was packed all summer with people sunning themselves at the spacious outdoor café. Step inside this fall, and you’ll find the same favorites: hand-cut Beef Tartare ($16), a vat of Belgian Mussels with fresh dill ($16), Fried Chicken Skins & Pickles ($9) and Brussels Sprout and Burrata Toast ($14). Executive chef Chris Curren knows the way to your heart is through new-fangled comfort food. 130 S. Michigan Ave., Chicago, 312-880-0130


My go-to before the symphony, I’m especially partial to chef Danny Sweis’ Artichoke Arancini ($7), the Burrata Salad ($12) and the Grilled Swordfish with capers and tomato passata ($23). The pizza is impressive, especially on Mondays, when pizza and any beer is just $10. Looking for a place in the Loop to meet someone for a drink and a bite? Check out their lovely bar area. 65 E. Adams St., Chicago, 312-786-9911

Photo courtesy of Tesori.
Photo courtesy of Tesori.

Halfway There: South Loop/Pilsen/University Village


This is serious food, prepared beautifully by chef Ryan McCaskey and served in a sophisticated space. You can opt for the five- or 10-course tasting menu and have the full two-Michelin-star experience, or belly up to the bar and enjoy the city’s most inventive (Gin and Tonic) Lime ($14) with a Maine Lobster Roll ($18) or a kick-ass Patty Melt ($16). 1639 S. Wabash Ave., Chicago, 312-360-9500

Photo courtesy of Anthony Tahlier.
Photo courtesy of Anthony Tahlier.

County BBQ

A Michelin Bib Gourmand recipient once again this year (that means great food at good value), this joint is presided over by chefs Michael Kornick and Erick Williams, who share a love for all things brined, smoked, and spice-rubbed. If you are a bourbon lover, you will find much to admire here, with over three-dozen labels on hand. Go for the Meat & Three ($16), a full plate with your choice of ribs, rib tips, brisket or chicken and three sides (don’t miss the Blackened Cauliflower with Parmesan and the Sweet Potato Fries with Sriracha Aioli). 1352 W. Taylor St., Chicago, 312-929-2528

Davanti Enoteca

Scott Harris had a proven track record with the Mia Francesca restaurants, but was looking for a more contemporary take on Italian cuisine here. If you don’t order the Focaccia di Recco ($17), I feel very, very sorry for you. Same goes for the Mascarpone Polenta with the Ragù of the day ($16/19), the Soppressata e Caciocavallo Pizza ($15) and the delectable Cacio e Pepe ($14) pasta, so simple and yet so damn good. 1359 W. Taylor St., Chicago, 312-226-5550


In the heart of Pilsen, you’ll find this dimly lit but charming restaurant, along with the subterranean Punch House and the always swingin’ Thalia Hall. Michelin just bestowed a star on Chef Jared Wentworth and this hip resto, where you’ll find the bar food of the gods: Wood-Roasted Olives ($6), Beef Fat Frites with Harissa Ketchup ($6), Wood-Roasted Blue Crab Dip with Artichoke Relish ($16) and their famous Juicy Lucy burger ($15). There’s also a killer Choucroute ($28), a fabulous craft beer selection and a deep cocktail program. Hipster never felt so good. 1227 W. 18th St., Chicago, 312-526-3851

Deep South: Hyde Park/Bridgeport


Über-cool and talented chef Matthias Merges (a Trotter protégé) was the first celebrity chef to venture down to Hyde Park and set up shop. His handmade pasta is well worth the trek — the Bucatini Carbonara ($20) with a 60-minute egg is perfection. But the man is equally adept with seafood, meat and game. It’s hard to go wrong at this Bib Gourmand winner. 1462 East 53rd St., Chicago, 773-288-1010

The Duck Inn

Everyone’s talking about chef Kevin Hickey’s latest hotspot, a gastro-pub with seriously delicious food (and another Bib Gourmand winner this year… I told you the South Side was happening!). Not surprisingly, duck features prominently on the menu: Duck Wings with Japanese BBQ Sauce ($10), Shrimp & Duck Spring Rolls ($9), and the show-stopping Rotisserie Duck ($62) meant for the table. But no one’s leaving without an order of the Fried Cheese Curds with Bloody Mary Ketchup ($8) or the high-end Gyros Plate ($26). They are necessary. 2701 S. Eleanor, Chicago, 312-724-8811

Pleasant House Bakery

If you’re an Anglophile, welcome to Nirvana. Chefs/owners Art Jackson and Chelsea Kalberloh Jackson are serving up individual Royal Pies — handmade flaky wonders — filled with all good things, like deeply flavorful Steak and Ale, curried Chicken Balti and the vegetarian Mushroom and Kale (all $7.95). Potatoes come in English “chip” form (i.e. thick cut and crispy) and topped with gravy; and British desserts abound (treacle tart, trifle, sticky toffee pudding and the like). Best of all, baker Wes Ervin (late of Publican Quality Bread) is milling grains and baking bread onsite daily. 964 W. 31st St., Chicago, 773-523-PIES

The Promontory

From the Dusek’s/Thalia Hall and Longman & Eagle team of Bruce Finkelman and Craig Golden comes this hearth-focused resto named for nearby Promontory Point in Burnham Park. Michelin-starred chef Jared Wentworth’s menu spans the globe, ranging from decidedly American (Brunswick Stew, Sweet Corn Hush Puppies) to Asian (Grilled Phoenix Tofu, Kalbi Beef Short Ribs) and Mediterranean (Ricotta Gnudi, Mezze Spreads, Porchetta). Come for the food, stay for the music. 5311 S. Lake Park Ave. West, Chicago, 312-801-2100 

Yusho Hyde Park

Chef Merges strikes again with a casual redux of the popular Logan Square restaurant Yusho. University of Chicago students and faculty are going crazy for this deliciousness: Charred Octopus with Green Beans and Enoki Mushrooms ($12), Grilled Salmon with Apple and Squash ($18), BBQ Chicken Ramen with Collard Greens ($12), Japanese Loaded Fries ($8) and more. Get in line. 1301 E. 53rd St., Chicago, 773-643-1652

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