Hometown Eats Part 2: A Chicago Culinary Tour

Hungry for more after his last culinary adventure in the Windy City, contributing writer Andrew Kaplan traveled from New York back to his hometown of Chicago to try some more local favorites. 

Once again, I was fortunate enough to have the opportunity to travel back to my roots: the great city of Chicago. While I always look forward to my family’s cooking, I am also always lured in by Chicago’s amazing and diverse selection of restaurants. From well-known hot-spots to locals’ favorites and from cupcakes to Latin sensations, I’m uncovering a handful of them for you, right here, right now.

My first evening kicked off with dinner at famed Chicago chef Art Smith’s Table Fifty-Two. With a short, concise and Southern-inspired menu, the only thing wrong with this restaurant is that I now need to go back and try the remaining items I did not get to sample this time around. 

Upon arrival, we enjoyed the delicious deviled eggs, an Art Smith classic. Shortly afterwards came the sizzling, hot, and cheesy Goat cheese biscuits. I could have had a couple plates of those and been just fine. 

For dinner, I ordered the Cornmeal Crusted Catfish with cheese grits, braised collard greens, a jalapeño hush puppy and some crispy okra. Light, crispy and flavorful, this dish delivered. Other entrées at our table included “Back to the Table” Crabcake, KC Lamb Bone-In Strip Loin, Fried Green Tomato Napoleon with Goat Cheese, just to name a few. We also sampled all of the sides, including the Sweet Potatoes with Maple Syrup, French Fries with Manchego Cheese and Smoky Paprika, Skillet Cornbread with Bacon Ends, Three-Cheese Macaroni (one of the best!) and authentic Southern-style Braised Collard Greens. We enjoyed a variety of desserts, but the crowd-pleaser for sure was the Hummingbird Cake – a banana cake with pineapple and pecans and cream cheese frosting. 

Table Fifty-Two is a small, comfortable restaurant that will make you feel like you are sitting in someone’s dining room – Art Smith’s dining room, as a matter of fact. Try to check it out on a Wednesday or Sunday, when they serve their (in)famous Fried Chicken.

(Table Fifty-Two, 52 W. Elm Street, Chicago, IL, 312-573-4000,

Breakfast the next morning was at Tempo. Tempo is known for their enormous omelets served in a skillet. I went ahead and ordered scrambled eggs with turkey sausage and toast. Beyond the omelets, the menu is your basic breakfast menu, but if you’re in the area, Tempo is a must. It is a perfect place for families, and is located just west of Michigan Avenue, right in the heart of downtown.

(Tempo, 6 E. Chestnut Street, Chicago, IL, 312-943-4373,  

That evening, I picked up dinner from Café Orchid, a small Turkish restaurant located just east of Roscoe Village. While it’s an unassuming little restaurant tucked into a strip mall just east of Lincoln, on Addison, I can see why I’ve heard that people tend to get addicted to this place. 

Our meal started off with Eggplant Musakka, a stewed eggplant, garlic and tomato dish that we ate as a dip. Along with that, we all shared the Iskander, which is a traditional layered Turkish dish named after the chef that created it. But it’s not the layered lasagna type of dish you might be thinking of! At Café Orchid, they start with small squares of buttery crunchy bread the size of croutons. From there, the Iskander is topped with slices of gyro meat (doner) and then spoonfuls of tomato sauce, all finished off with a cooling yogurt sauce. This dish was “interesting” in its concept and its bold flavors were representative of this restaurant’s overall menu.

(Café Orchid, 1746 W. Addison Street, Chicago, IL, 773-327-3808,

The next day’s lunch ushered in a Jibarito from Boriquen. Boriquen is right around the corner form my brother’s house and I have glanced at the sign every time I’ve passed it, but I’ve never stopped. Today was the day. 

A jibarito is a Puerto Rican sandwich that starts with two pieces of fried green plantain that act as the bread. You can fill it with your choice of pork, meat or chicken, along with mayo, garlic and lettuce. I was trying this sandwich more for the hype, but soon after the first bite, I became a true fan. 

(Borinquen, 3811 N. Western Avenue, Chicago, IL, 773-442-8001,

For dinner that evening, I stuck with the Latin theme and decided to pick up food from a little Mexican place called La Cabana de Don Luis. This came on recommendation from a friend who lives in the area. I ordered Tacos al Pastor and my brother ordered the Steak Burrito. We both enjoyed this fresh tasting, very reasonably priced Mexican food and agreed we would go back. Add it to your go-to list of local Mexican joints.

(La Cabana de Don Luis, 5157 N. Lincoln Avenue, Chicago, IL, 773-271-5176)

After dinner, it was time for a cupcake tasting. Earlier in the day, I had picked up some beautiful looking cupcakes from More cupcake bakery. The question was: Could they possibly taste as good as they looked? We cut the cupcakes into quarters and took bites to try for ourselves. Our top three were the Salty Caramel, S’mores and Lemon Meringue. The Salty Caramel was a white cake with a caramel filling that oozed out and had a vanilla buttercream on top with some salt flecked throughout. It was amazingly delicious, especially if you’re a salty-sweet fan. The S’mores was chocolate cake with a marshmallow filling and a vanilla frosting with some graham cracker and a toasted marshmallow on top. Last, and certainly not least, was the Lemon Meringue. This was a white cake with a lemon filling in the middle and the classic meringue top that acted as the frosting. 

These cupcakes lived up to their name (and their looks!): After trying one, you will definitely want More. Don’t miss out if you’re nearby.

(More, 1 E. Delaware Place, Chicago, IL, 312- 951-0001,    

The next night, neither my brother nor I had eaten dinner. We were both in the mood for chicken wings, so we decided to order from the newly opened Wing Stop. Yes, Wing Stop is a chain and I’m usually not the biggest fan of chains, but we took the plunge. We ordered half of the wings with a Hawaiian sauce and half with the original hot sauce. The Hawaiian was similar to teriyaki, but had a sweet kick to it. 

Whenever I’m in doubt, I order my wings well-done. And, I’m more of a fan of the smaller bite-size wings than the huge chicken wings that basically resemble a drumstick of a regular chicken. These wings were small, crispy and flavorful and definitely did the job. While I do like supporting the small, neighborhood restaurant, the wings at Wing Stop are a good thing for this, or any, neighborhood. 

(Wing Stop, 3326 N.Western Avenue, Chicago, IL, 773-697-0009,

Lunch on Saturday was at the famed Chicago institution, Superdawg. Superdawg has been around for years and is hailed as one of Chicago’s first and finest hot dog joints. I ordered a “Whoopskidawg,” which is a Polish sausage grilled and basted with barbecue sauce and served with grilled onions on a freshly baked onion roll. I have never had a Polish made in this way, but it was pretty tasty. My brother had the cheeseburger and my nephew had the signature dog, the Superdawg. 

While Superdawg is not too conveniently located in the city, if you have a car and can venture out, the journey, let alone the Superdawg experience, is well worth the trip

(Superdawg, 6363 N. Milwaukee Avenue, Chicago,IL, 773-763-0660,  

Brunch the last day was at Sola Restaurant in Chicago’s Lakeview area. I had tasted Sola’s burger in the past, which has won plenty of accolades, but their brunch menu was new and appealing to me. Chef Carol Wallack prepares interesting food with a little Hawaiian flare. 

My mom, aunt and I split everything. We started with the Malasadas, which are Portuguese-style donuts. They were round, puffy balls of donuts, fried and tossed in sugar and served with mango curd and raspberry sauce. We also ordered the Chilaquiles, which was a tortilla hash served with eggs, pico de gallo and guacamole. Along with that we had the Pineapple Upside Down French Toast. This super tasty dish could easily have been featured as a dessert – it was caramelized on the bottom and topped with little bits of pineapple and a vanilla sauce. Last was the Matzah Brei, a traditional Jewish breakfast dish with matzah and egg. This was served in the style of Chef Carol’s Grandma, with fennel, onion, spinach and Boursin cheese. As a side, we had the Togarashi Hashbrowns. A seven spice Japanese blend, the shichimi togarashi added a kick of spice to these tasty, golden brown, crisp hashbrowns, Overall, this was a near perfect brunch. I can’t wait to go back for dinner!

(Sola, 3868 N. Lincoln Avenue, Chicago, IL, 773-327-3868,

Chicago never seems to let me down when it comes to good eating. And, I promise not to let you down with my recommendations – you’re in good hands. I’ll be back in a few weeks, so if you have any Chicago recommendations, please send them in!

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