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More Than Just Tourist Traps: A Love Letter to Two Chicago Sports Personality Restaurants
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More Than Just Tourist Traps: A Love Letter to Two Chicago Sports Personality Restaurants

Greg Stegeman
Published about 1 month ago

I spend a lot of time thinking about, talking about, preparing/ordering, and eating food. It’s actually a staggeringly important part of my daily schedule. And if I run into someone looking for a recommendation, I’m all too eager to share some input, go over the highlights of a given menu, or offer my review of the service. Sometimes I’ll chime in on conversations of strangers on the street, or at a neighboring table. I don’t need much of an opening. All it takes is a small overhead question about what to order, or what’s good. This occasionally makes my wife uncomfortable. Who knows why. Maybe it’s obnoxious. “Alright,” she’ll say, hoping I lose my nerve, or realize that it might be embarrassing. I don’t. Ever. I think food choices are too important. Sure, for most folks, their current meal will not be their last (thank goodness), but that doesn’t mean it should be gruel-like and unenjoyable. Why have a dodgy meal if you can help it? You shouldn’t!

Food is an integral part of our survival. As such, we spend time consuming it. A lot of time. I haven’t personally added it up, but according to some astute Googling, the average American spends 32,098 hours eating and drinking. Yow! Additionally, food has the ability to bring pleasure, inspire emotions, and spark memories. As a result, I think it’s important to make each dining experience an enjoyable one. So, I share my thoughts, opinions, and recommendations with others. If I can help, I want to. It’s for the good of humanity, doggone it! After all, a well-fed, and well-satisfied population is prone to greater levels of benevolence, patience, and happiness. At least I am when I’ve had a dynamite meal. How about you?

Anyway, Chicago has plenty of dining options out there, and like any normal human being, I have my preferences. By and large, these preferences are of a certain (high) quality. That’s not to say I don’t have my own personal dives or haunts. It is to say that I have what’s known as champagne taste. If you want a dive or haunt to visit, I’m happy to share, but most of my suggestions cost some money, serve name-brand and/or high-grade meat, and have nice beer, wine, and cocktail lists. Despite making this all too obvious, whenever I go through my list of curated and recommended eateries in Chicago, two restaurants, in particular, get surprised looks from people who have never been: Ditka’s and Harry Caray’s Italian Steakhouse.

I have no definitive insight into why that is, but I could venture a guess. I’d imagine people think something along the following: “With a number of celebrity-chef-run spots, and a plethora of Michelin-starred, and James-Beard-award-winning restaurants in the area, you, YOU, you, Mr. Champagne Taste, are recommending one restaurant named after a retired football coach, and another named after an old Chicago baseball announcer? Really?” My answer to that is a resounding, unequivocal, and effusive: yes! Before I go on, get too emotional, and get carried away, I have to pause and remember that the restaurant business is a hard racket. Many big-name sports personalities have tried their hand at it and failed. Heck, it extends into the entertainment world too. Remember Planet Hollywood? The restaurant repped by the star power of Schwarzenegger, Stallone, and Willis, each in their respective primes? Can’t miss, right? Wrong.

Unfortunately, many sports or entertainment-personality restaurants focus too much on the gimmick. They fill their restaurants with memorabilia, tchotchke, and trinkets. They get caught up in the celebrity aspect and think that’s all they need to sell it. They count on patrons saying, “Hey, look at that picture,” or “Check out that jersey,” or “Wow, that’s a cool autograph,” and being impressed enough with all of that to come back. Then, they falter, struggle, and ultimately, fail. Hello, Planet Hollywood. The great C.S. Lewis once wrote, “Put first things first and we get second things thrown in; put second things first & we lose both first and second things.” Ultimately, the standard gimmick-driven, personality-themed restaurant puts second (or third) things first—the celebrity. That picture on the wall doesn’t get repeat business and, as any successful restaurateur knows, new customers are great, but repeat customers are the backbone.

What makes both Ditka’s and Harry Caray’s different? In preparing for this article, I touched base with with Paul Woodard, Managing Partner at Ditka’s and Grant DePorter, CEO of Harry Caray’s Restaurant Group, respectively. Paul told me, “The biggest misconception is that we are a sports bar. We do have a sports bar but we are so much more than that.” This “so much more” is what separates places like Ditka’s and Harry Caray’s from all the rest. But what does that mean? As Paul said, “Ditka's restaurant is all about two things. Delicious American-style food and fantastic service.” Similarly, Grant said, “From the very beginning we always wanted to make food and service the primary focus.” There you have it. Ditka’s and Harry Caray’s differ from the also-rans in that they put first things first—the product: food and service.

Okay, if you haven’t been to either spot, I know what you might be thinking: Is the food and service good for a sports bar, or actually good. The answer is both! As Grant from Harry Caray’s shared, “We serve great food, from USDA Prime steak to a Chicken Vesuvio voted best in the city, to award-winning housemade bar chips.”

If you want to take in a game at the bar, you’ll have a knockout snack, a perfect complement to a nice, cool Budweiser—just like Harry might drink! Then again, if you want to have a power meal with business associates or a romantic dinner with your significant other, Harry Caray’s has you covered there too. Their steaks are delicious. My favorite is a tender, juicy, wet aged New York Strip. And get this: You can get the strip dry aged or grass fed too! Does that sound like your typical sports bar? I didn’t think so.

If you’re not into steaks, that’s fine. Harry Caray’s has a wide range of Italian fare, from the aforementioned Chicken Vesuvio, to a great Rigatoni alla Vodka, Chicken Parm, and Pappardelle alla Bolognese. They also have one of the best seafood salads I’ve ever had.

On the Ditka’s side, their signatures are the pork chop, pot roast nachos, banana cream pie, and Bloody Mike.

Now, you might be thinking, “That sounds pretty basic.” It isn’t. It’s high-end, gourmet-style comfort food. It might sound simple, but quality cannot be underestimated, and Ditka’s takes quality seriously. Paul filled me in on the attention each item gets, saying “[Ditka’s uses] a Berkshire chop, which is the highest grade of pork. The pot roast nachos take three days of prep to get ready for the table. We make the chips daily, and whatever is left at the end of the night is tossed out. The banana cream pie is made fresh every day and the best part about it is the layer of fresh bananas right in the center. [Finally] the Bloody Mike is our own recipe. The seven ingredient skewer is a welcome surprise the first time it hits your table. In addition to that, we also give you a chaser of our Iron Mike's Ale that is made just for us from Haymarket Brewery.” How many bars spend three days making their nachos? Slim to none. How much better are Ditka’s nachos than any other nachos I’ve ever had? Tons. It’s not even close. The pork chop and banana cream pie are also as good as they sound. Actually, no, they’re better.

While Paul was only talking about their signature dishes, I’d be remiss if I didn’t also mention some of Ditka’s other hits. Like Harry Caray’s, Ditka’s has a range of steak options, great for both your wallet and your palate. I like the 16-ounce New York Strip, but I could just as easily go with their prime rib. I’m typically not a huge prime rib fan, but the rub they use is out of this world.

They also have a wide range of homestyle favorites like the meatloaf stack, fried chicken, burger, and perch dinner with the best tartar sauce I’ve ever encountered. On the weekend, don’t forget about breakfast either. It’s the most important meal of the day, you know! They make one of the few, genuine-style Belgian waffles around, with the caramelized sugar creating a sweet, crispy coating that leaves you craving more. Additionally, their special event brunches, like the one on Mother’s Day at the downtown location, is one of my favorite buffets, with all the Ditka favorites, a raw seafood bar, and all-you-can eat portions (perfect for a growing, albeit outward boy like me!).

Truth be told, there was a time when I would go to Ditka’s, on average, at least once a week. Additionally, it’s been at the center of some pretty special moments in my life. The night I proposed to my wife, we ate at Ditka’s. The day my son was born, once we were settled at the hospital, my wife sent me to grab a bite to eat because I was “no good to her hungry,” and I went to Ditka’s. My rehearsal dinner was held at a suburban Ditka’s outpost. My family loves it. Obviously, the food is important, but the service takes it to another level. This is intentional, and an integral part of their success. Paul said, “You have to have great service. Not good service, but great service. It is always the personal touches that our staff gives to the guest that make [them] feel wanted here. Being wished “Happy Birthday,” or “[Happy] Anniversary” when you walk in the door; remembering your drink order when you sit; knowing what you are going to get for dinner. It's always the little things.” He’s right, and it’s why Ditka’s has a special place in my heart. According to Paul, this philosophy produces a steady stream of repeat business. In fact, one in four out-of-towners become repeat customers, and one in five locals turn into regulars—like me.

While I haven’t been to Harry Caray’s quite as frequently, it is a definite favorite of mine, and, their service plays a crucial role too. A lot of that comes from Harry Caray, himself—a jovial guy. According to Grant, “If [Harry] wasn’t at a baseball game, he was at a restaurant or a bar. He loved the people, and he loved hanging out in restaurants and bars.” This translates the second you walk into the door. Whether you’re a first-time customer, a repeat visitor, or a regular, you’re treated like an invited guest—someone whose presence is wanted. You’re “company.” The host or hostess is warm and inviting, the servers are friendly without upselling, the bathroom attendant is collegial, and the people in the restaurant are down-to-earth. According to Grant, this has generated “A very strong customer base, whether they’re local, or they come in once a year.” Remember, repeat business is the backbone of a restaurant’s success. As Grant shared, “Stan Lee came in one year, and then next thing you know, he shows up again. A-Rod once came in on a roadtrip, and next thing you know, he came in every single day he was here.” In a market like Chicago, this does not happen unless you take the food and the service seriously. Celebs who could go anywhere don’t come back unless they’re treated well, their hunger is satiated, and their cravings are satisfied. What’s more, regular Joes don’t spend their hard-earned dollar on dry, over-cooked, once frozen foods and sub-standard service.

In addition to the food and service each spot provides, my interactions with Paul and Grant revealed a few other things that contribute to the success of their respective restaurants. Both are heavily involved, their name partners are heavily involved, and they stay relevant and accessible. Paul can often be spotted on the floor at an area Ditka’s location, not in a back office. Iron Mike himself stops in for a bite frequently. At Harry Caray’s, Grant stays involved and told me “Dutchie Caray [Harry’s widow] is around a lot.” He continued, “Though Harry isn’t around anymore, a lot of his friends are, and they keep it fun.” Each joint has been around for years (Harry Caray’s since 1987 and Ditka’s since 1997) and they remain relevant and accessible with multiple restaurant locations, menu tweaks that stay up on current trends, and community involvement. As with any successful individual, organization, or enterprise, Paul, Grant, and their respective teams exhibit a passion to be great, the hands-on involvement to make it so, and the continued desire to avoid complacency.

The next time you’re in The Windy City, whether you make your home there, or you’re just visiting, you really should consider these two great, Chicago-sports-personality restaurants. They’re certainly worth a try, and I’d argue they’re worth your repeat patronage. That they happen to be affiliated with two larger-than-life-Chicago-sports legends, and each have a museum’s worth of cool memorabilia inside, is secondary to the exceptional food and service you’ll find at each. Their prolonged and sustained success in a market as competitive as Chicago, in an already tough industry, within a subgroup that struggles to find longevity is a testament to their quality. So, whether you’re looking to take in a game and a meal with some friends, enjoy a relaxing and elegant surf-and-turf dinner with wine with your spouse, have a Chicago meal at a Chicago spot on your vacation, or host a large event for family and friends, keep Ditka’s and Harry Caray’s on your short list. You won’t be sorry, and after reading this, you shouldn’t be surprised either.

Harry Caray's Italian Steakhouse,
Ditka's Restaurant Chicago

About the Author

Greg Stegeman

Greg is a Chicago guy who likes to cook, dine, and help others navigate their food choices. Why? Because food is an integral part of our lives, he's the best version of himself when he's well fed, and he wants to help others more consistently make a routine activity into something special. When he's not writing, he's watching sports, searching out ways to laugh, offering unsolicited-yet-rational positions on social media, handling the domestic responsibilities of a husband and dad, and figuring out his next meal.

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