Booby's Charcoal Rib

Name: Bobby’s Charcoal Rib

Location: Niles, IL

Meal: Skirt Steak Sandwich, Fries, Cole Slaw, and a Coke

Type: Sandwich Shop

One of the culinary strengths of Chicago is that every neighborhood can be home a dozen great restaurants all representing different cuisines. Located to the north, Niles is one of the old Chicago suburbs and has the food heritage that comes with it. In determining where to eat during my limited time in Chicago, I kept hearing about Booby’s.

(Let’s just take a moment for the 11-year-old kid in all of us to giggle at the name.)

Booby’s is a old-school Greek owned counter service sandwich shop. They serve everything from sandwiches and gyros to salads and the ubiquitous Vienna Beef hot dogs.  The star of Booby’s is the steak sandwich, a healthy slice of skirt steak char-grilled,  smothered in BBQ sauce, and served plain on crusty bread that has just the right amount of chew to it. The sauce, despite being generously applied, is not overpowering; it provides just the right amount of flavor, letting the grilled taste really shine. Accompanying the meal were fries and cole slaw. Neither of them were too remarkable but that’s not their role, they direct the attention to the sandwich’s simplistic perfection.

As a visitor, and likely a resident, you’ll never have enough time fully explore all that Chicago has to offer your stomach. Booby’s makes my shorter list and I think you’ll agree it is worth it. My only advice, pay cash if there is any concern of Booby’s showing up on your credit card statement.

Steak Sandwich Lunch

More pictures after the Jump

Perfect crust to the roll

Steak Sandwich

Cole Slaw

Italian Beef

Name: Portillo’s

Location: Greater Chicago

Meal: Multiple (Italian Beef, Chop Salad, Garbage Salad)

Type: Local Restaurant

Portillo’s is one of my favorite restaurants when it comes to Chicago food. What they do best, is doing so many things well. Not only do they serve one of the best Italian Beef sandwiches around, they also serve great Chicago style hot dogs, and they also serve some of my favorite salads. They do this while providing some of most consistently great service I’ve ever experienced. In the two years that I have visited the Chicago area, I would say that I’ve eaten at Portillo’s more than five times; once even for lunch and dinner in the same day. For someone who prides himself of being the Hungry Traveler, always looking for another place, that is saying something.

Lots more after the jump.

The Italian beef is one of Chicago’s best; most will agree that an Italian beef isn’t complete until it has either the sweet or spicy peppers on it (or both). As a reader of this site can quickly figure out I don’t often order a salad. My aversion to salads is not a result of any dislike of them; rather most salads on menus across the country tend to be fairly boring (and you can’t deep fry a salad…yet!). The salads are Portillo’s are anything but boring. The first is the Chopped Salad made with lettuce, chicken, bacon, tomato, Gorgonzola, green onion, and pasta. Yes, they mix cold pasta into their salad with terrific results. The second is the Garbage Salad with lettuce, fresh radish, salami, provolone cheese, roasted red pepper, and celery. Both of the salads are familiar to me but notched up just a few levels by adding the right ingredients for taste and texture. Portillo’s also is unique with what they serve their salads with. No hard hunks of bread here, Portillo’s serves their salads with a warm lemon poppy muffin. You wouldn’t think a muffin would work with a salad but it does.

Portillo’s really is great food. If you were going to Chicago and only had time to try one restaurant I’m pretty sure Portillo’s would be recommendation, if only for sheer number of option within their menu. Portillo’s really says Chicago better than most restaurants; and Chicago has a lot to say.

Garbage Salad

Chopped Salad

Close-up of Chopped Salad

Italian Beef

Sweet Peppers make an Italian Beef

Portillo's at night

Al's Italian Beef

Name: Al’s Beef

Location: Chicago, IL

Meal: Italian Beef sandwich, Cheese fries, and Pepsi

Type: Sandwich

Chicago, besides being a great city of its own right, is a city torn between three culinary poster-children. You can find good support for the Chicago hot dog, the deep dish pizza, or the Italian beef being the food to best associate with Chicago. As previously mentioned, I have love for the Chicago hot dog, but for my money Italian beef is Chicago to me.

Lots more after the jump. To be fair, I’m originally from outside of Philadelphia and biased towards the awesomeness that is a Philly Cheesesteak, primarily a beef sandwich with a chewy roll. A good Italian beef sandwich doesn’t always have a chewy roll, it softens and mushes up by the time you’re done eating it. It is a sandwich that is a study in flavor: beefiness, sweet and savory peppers, hot and spicy peppers, and garlicky goodness.

The cheese fries are good, the fries in particular are fresh-cut and the cheese is every bit the manufactured gooeyness you want. This is a meal that really benefits from an ice-cold Pepsi; it cools the spice of the peppers and provides just enough bite to be delicious. If you’re going to Chicago, for the purpose of eating just go ahead now and book a return trip. There is no way you’d be able to eat all of Chicago’s best in one trip but when you’re there start with an Italian beef, you’ll be happy you did.

Italian Beef

Cheese Fries

Pepsi

Fresh made Frontera Salsas

Name: Frontera Grill

Location: Chicago, IL

Meal: Margaritas, Guacamole, Flautas, and Tacos Carbon

Type: Mexican

Rick Bayless is amazing. I’m pretty sure any of the words I could write up about my experience at Frontera Grill would distract from that key point. From my personal experience I can tell you that everything you’ve seen on Top Chef, in newspaper profiles, or his own show is absolutely true; this man knows how to cook. I will note that you shouldn’t plan a trip to Frontera if you expect to catch a glimpse of Chef Bayless. To me, him not cooking the food is a non- issue; developing such a strong program that it continues to soar without him is a testament to expertise in the restaurant business. The entire meal was great from the subtle heat of the guacamole to the pleasant orange sweetness of the flautas to the smoky beans served with the tacos. The service was impeccable. What Chef Bayless also deserves a lot of credit for is keeping such highly applauded food accessible. As much as Frontera is raved about the prices were maybe $2-$3 more than the chain Mexican restaurant by my apartment in the suburbs. Go, be prepared for a wait, but expect to leave thoroughly impressed with your experience.

Lots more pictures after the jump.

Guacamole and Chips

Topolo Margarita

Flautas de Puerco

Tacos al Carbon

Cebollitas Asadas

Frontera Grill

Superdawg

Name: Superdawg

Location: Chicago, IL

Meal: Chicago-style hot dog and a chocolate milkshake

Type: Hot Dog Joint

As previously noted Chicago food is a food lover’s paradise. Two foods in particular scream ‘Chicago’ to the outside world louder than anything else: deep dish pizza and the Chicago-style hot dog. As someone who drew up outside Philadelphia with the Pat’s vs. Geno’s cheesesteak debate I find it interesting that with so many independent hot dog stands in Chicago there is not the contention title of ‘best’ the City of Brotherly Love provides. The hot dog stand that normally tops the lists and gets the calls for television shows is Superdawg. Superdawg has be operating for over 50 years and still provides friendly carhop service. Located in a largely Polish neighbor on the North Side of Chicago you’ll be able to find it quite easily thanks to their famous hot dog characters on the roof. What awaits you after you park is the pride of a city tucked inside a small box, covered in fries.

A Superdawg is is constructed of a steamed hot dog in a poppy seed bun topped with: yellow mustard, bright green relish, chopped onion, a whole dill pickle spear, and a pickled green tomato. The hot dog is then stuffed in a box and covered up with french fries. Chicagoans pride themselves on pointing out that ketchup is not an option. I was willing to indulge them though I have been known to top a hot dog with ketchup every now and then (Pennsylvania kids are raised to love Heinz). The hot dog comes together well, this is no 7-11 quickie dog so you’re in store for some bold tastes and a some rewarding chewing. The pickled tomato is an acquired taste, of course I tried it but I wasn’t a fan of its acidity so I moved on after a nibble or two. The fries are good, apparently they are made fresh on site ; I have no complaints but they weren’t the greatest fries I’ve ever had . The star of the meal is the hot dog: plump, juicy, delicious.

Chicago-style hot dogs are on my top American foods list, not the top 5 or 10, but probably the top 25 list. Chicago is quite proud of their hot dog and likes to point out the differences of theirs compared to the rest of country (they like doing this with pizza too). Being a working town Chicago is well represented with their hot dog, its utilitarian, honest, and luckily delicious.

Superdawg Box

The iconic Maurie and Flaurie Superdawg

Harold's Chicken Shack

Name: Harold’s Chicken Shack

Location: Chicago’s Southside

Meal: Quarter Chicken with mild sauce, Fries, Cole Slaw, and a Pepsi

Type: Chicken joint

You could write extensively on just the wonders of Chicago cuisine, both highbrow and lowbrow. My limited travels to the Windy City have only amounted to a very tiny scratch on the surface of Chicago cuisine. I like to think that in my limited experience I’ve been able to get to parts of the Chicago short list. On Chicago’s Southside, Harold’s Chicken Shack is an institution, plain and simple. For over 50 years, Harold’s has not only been providing great food to some neighborhoods others chains would scoff at, they’ve been making some of the best tasting chicken there is.  This is another one of those places people say to expect a 30-45 minute wait for your food; I was eating within five minutes of ordering.

I don’t remember which Harold’s I visited; I was on my way from Navy Pier to Midway and my GPS wasn’t cooperating but I found one nonetheless. From what I’ve read this was one of locations, there was no bullet-proof glass at the counter. The chicken is fried in a mixture of beef tallow and vegetable oil, unlike just about everyone else I’ve ever heard of. Beef tallow? Rendered beef fat, the stuff even McDonald’s stopped using in 1990, so yes it makes fried food DELICIOUS. As a result of the extra attention the chicken receives and the oil/fat it is fried in the chicken has an amazing crunch to it. I’ve had chicken that was harder before, over fried that is, Harold’s is a special kind of crunchy. The crunch of Harold’s can be soften up by their sauce, you choose one of three: BBQ, mild, or hot. I went with mild sauce which was liberally applied to my entire order. An order normally consists of your chicken, fries, and white bread all covered in sauce and crammed inside your standard white styrofoam takeout container with cole slaw on the side. I ate in, popping open the styrofoam as quickly as possible and was met with chicken nirvana. You will not have perfectly clean fingers after Harold’s despite your best finger licking abilities.

The chicken is great, crunchy yet moist on the inside with the sauce having just enough heat and vinegar to perfectly compliment it. The heat of the chicken steams the bread just right. On their own, the fries aren’t much to talk about, pre-frozen and likely dumped out of a brown bag; the sauce Harold’s uses take the fries to a much better place. I had done an little research into Harold’s and found that to truly have the experience, I need to finish off my meal with a fry sandwich; folding up some of the sauciest fries into one of the pieces of bread. I’m glad I took the advice, a Harold’s fry sandwich is a nice finish to all together great meal.

Chicago is an amazing city, I spent only a few days downtown and on the last day realized how little I actually had seen. I hope to get back there soon and explore, remember what I say, “have stomach, will travel.” Chicago is known to the outside world most for two foods, deep dish pizza and Chicago style hot dogs. I will not deny that both of those foods are great and represent the city in their own way. I argue that Harold’s delivers not only equally great food but also an equally important representation of the city.

Fry Sandwich