Vacation Tip: Where to Eat in Chicago

A restaurant has to be really exceptional for me to give it a five-star rating. Harry Caray’s Italian Steakhouse on West Kinzie was that good. After a long day visiting the Shedd Aquarium and strolling around sunny Chicago, we were all starving. The kids and I decided to try an early dinner at the famous River North landmark. A sophisticated sports bar, with ties to Al Capone, there is plenty of other interesting history behind the restaurant. Adored by fans from near and far, Harry Caray was a famous sports announcer who ultimately landed at Wrigley Field. There he became the voice of Chicago baseball, best known for singing “Take Me Out to The Ball Game” during the 7th inning stretch and exclaiming “Holy Cow!” He had a huge impact on the game and those who loved it.

The first indication that this was an above-average restaurant was when we arrived fifteen minutes early for our reservation. Rather than giving us a hard time or making us wait at the bar, the hostess welcomed us with a smile and seated us instantly. When I saw the spotless white tablecloths, beautifully set tables, and smart-looking waiters, I worried that we were underdressed. If we were, our servers gave no indication that they found our appearance lacking. The three of us were treated like royalty through the entire meal.

We began with cocktails, a Navy Pier (Julia), a Cosmopolitan (Calvin), and a glass of red wine (boring me!). Next, we ordered appetizers. We shared sausage & peppers crostini, a colorful medley of fresh Italian Sausage, red, green, and yellow peppers, and red onion with salsa verde on garlic toast, and toasted ravioli-a mix of four cheese and Italian sausage raviolis. Both were delicious.

Next it was time for the serious business-ordering the meat that Harry Caray’s is renowned for. Our knowledgeable waiter explained that most of the Midwestern beef is corn-fed (my personal favorite) and many cuts can be ordered either dry or wet-aged for maximum tenderness and flavor. Julia chose the wet-aged New York strip, Calvin the dry-aged Rib Eye, and I got the Filet Mignon. We shared tastes and each one was fantastic. I was particularly impressed with my perfectly-cooked medium rare cut, as that seems to be the hardest for most chefs to master. Though the steaks can be requested with “crusts” such as peppercorn or horseradish, we chose to go the purist route so as to experience the full essence of the meats.

This is a quality over quantity restaurant, and the entrees do not come with sides. However, we each ordered one. My BLT Wedge salad was phenomenal-the ideal balance of cool, crisp iceberg lettuce, Applewood bacon, and Roma tomatoes lightly drenched in bleu cheese dressing and crumbled Gorgonzola. The ideal complement to my filet! Cal’s asparagus was excellent too. Julia tried the bacon cheddar potato. It was delicious, but so big she couldn’t possibly finish it, even with our help.

A review wouldn’t be complete without describing the waitstaff. Everyone was outstanding. As with any extraordinary experience, it was all in the details. The waiters were immaculately dressed and so professional that Julia asked “Do they have to go to waiter school to work here?” Though Cal and I laughed, it was true. Our water glasses were kept full throughout the meal. Plates were removed at exactly the right moment, never too quickly or after sitting in front of us for fifteen minutes. Our server was informative, without lecturing or being condescending. Every single item we ordered appeared hot, fresh, and in a timely manner. When we were finished, one man even managed to produce a “crumb scraper” (aka table crumber) to clean off the tablecloth for us, an old-fashioned gadget harkening back to earlier days that somehow managed to be quite touching. At Harry Caray’s you are made to feel both like an honored guest and completely at home, a delicate balance that few eating establishments are able to achieve.

Harry Caray’s is not cheap, but this is a true instance of “You get what you pay for.” I don’t regret a single penny spent. The only regret I do have is that we didn’t save room for dessert. The table next to us apparently knew better! When I saw their key lime pie and hot fudge brownie sundae skillet, I vowed to return to this wonderful eatery the next time I’m in the area!

Five stars!

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