A nighttime view of the exterior of Chicago's famous Harry Caray's Tavern illuminated by a soft winter light

Restaurant Review: Holy Cow! River North’s Harry Caray’s blends history, sports and impeccable dining

A nighttime view of the exterior of Chicago's famous Harry Caray's Tavern illuminated by a soft winter light

As a lifelong Chicago sports fan, who was lucky enough to cover and report on every sport Chicago has to offer, Harry Caray’s restaurants in Chicago and suburbs hold a special place in my heart. 

Blessings to wunderkind Grant DePorter, the President and Managing Partner of Harry Caray’s Restaurant Group, who has created seven unique tributes to the late, legendary Hall of Fame Chicago Cubs-Chicago White Sox broadcaster Harry Caray (The ‘Godfather of the Seventh Inning Stretch’) and his passion for all things sports and finely crafted Italian-American cuisine.

You won’t have a bad meal anywhere at any location, from the Magnificent Mile to Lombard. But the focus of this review is the first and in my opinion, the best of them- their River North location, which serves families and singles with equal fervor and care. 

River North- Where It All Began 

Harry Caray’s Italian Steakhouse opened in River North in 1987, as their website states, “to celebrate the Hall of Fame broadcaster and his love for Chicago sports, great food and drink—and most of all—the fans.”

It somehow seems appropriate that the irascible Caray would choose an historic landmark building with a storied past—Frank Nitti, the infamous enforcer of the Al Capone gang, had an apartment on the fourth floor of the building. Guests can check out relics from the gangster-era in Frank Nitti’s Vault, including a once-hidden underground tunnel. They’ve also uncovered evidence that the building  housed a speakeasy and two illegal slot machine manufacturing companies in the 1920’s. 

It seems proper, then, that an Italian Steakhouse was the perfect venue for Caray and DePorter to showcase such remarkable pre-lunch and dinner snacks as Harry Caray’s award-winning, handmade Holy Cow!® Potato Chips, a staple at their bars, selected as the “Best Munchie in America” by Reader’s Digest. 

Their peerless starters include a TUSCAN CHARCUTERIE BOARD, a shareable meal in itself with apple watercress salad, horseradish mustard aioli, Genoa salami, Soppressata (dry-aged Italian salami) Capicola (dry-cooked pork), Speck (smoked ham), Pecorino Toscano, Dolcelatte Gorgonzola, Manchego,  Cerignola olives, artichoke hearts, crostini, and tomato jam. Don’t miss their GRILLED OCTOPUS, with roasted Yukon potatoes, Fresno chiles, watercress, and olive oil. 

There’s and reason why the Chicago Tribune voted Harry’s CHICKEN VESUVIO the “Best in the City.” I vouch personally for this moist, succulent, half chicken or boneless breast (I had the boneless breast) served with quartered potatoes and sweet peas, in a garlic and white wine sauce. Yum! My dining partner that day had their HOLY COW!® BURGER, served your way with candied Applewood smoked bacon, smoked gouda, lettuce, and Harry’s steak sauce, on a brioche bun. Their 18oz KANSAS CITY STRIP STEAK isa rare Chicago treat, a tender, flavorful, wet-aged rich cut of beef. Their 8oz FILET OSCAR is accompanied with crab, grilled asparagus, Bernaise sauce, and bordelaise. 

Pastas are a must, whether as an entrée or a starter. SHRIMP SCAMPI boasts linguini, Roma tomatoes, toasted garlic, red pepper flakes, basil, and a white wine butter sauce. TENDERLOIN LINGUINE pairs their beef tenderloin with shallots, roasted red peppers, baby arugula, portabello and porcini mushrooms in a sherry cream sauce. 

Pair the entrées with shareable sides such as CHARRED BROCCOLI withgrilled scallions, vinegar peppers, and fried capers, or CRISPY BRUSSELS SPROUTS, with honey vinaigrette, scallions, and red chili flakes.

HARRY’S TIRAMISU is a specialfinale to the meal …delicious layers of espresso and Grand Marnier-soaked ladyfingers, with mascarpone cheese, whipped cream, chocolate sauce, and powdered sugar. Or, FLOURLESS CHOCOLATE TRUFFLE CAKE has a raspberry coulis and topped with whipped cream.

Nitti’s Supper Club and Interactive Show 

​Harry Caray’s has turned its second floor into a speakeasy/supper club. From Saturday October 5-Saturday, February 15, they’re presenting a madcap interactive show, “WHO KILLED EDDIE O’HARE?” Described as a “True Crime History Mystery Musical,” for $80 per person, guests can enjoy a three-course meal as well as stepping into the role of partygoer at Frank Nitti’s birthday, and delving into the unsolved murder of Edward J. “Easy Eddie” O’Hare — Al Capone’s lawyer and father of war hero Butch O’Hare, for whom the airport is named. Dinner begins at 6:30pm, the show will begin once everyone has been served their entrée. For tickets, click here.

Harry Caray’s Italian Steakhouse is located at 33 W. Kinzie Street. They are open Sunday-Thursday from11:30am – 10pm. Friday and Saturday, they are open from11:30 am – 11pm.  For reservations, click here

Alison Moran-Powers and Dean’s Team Chicago