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An insiders' Chicago

Must-eats and other tips on visiting the Windy City.

A not-so-elevated El train stop, Chicago.
A not-so-elevated El train stop, Chicago.

“Tell Johnny Golf Shoes that you want a Ken Caminiti, and that Patty Ohio sent you,” the server at Big Bowl tells me.

Am I seriously being told to go to a random bar with this message? Yes I am. Am I going? Definitely. And yeah, I’m in Chicago. Patty Ohio is showing me one of the three things Chicagoans love: insider connections. The other two you ask? Their history and traditions.

One of the city's proud traditions: the Chicago-style dog.

But let’s get back to the beginning of the trip. I’m with my Chicago buddy Jay riding the El train (the “el” is short for “elevated”) headed to his mom’s home on the West Side. This train first ran its course in 1892 – part of it, anyway – making it the second-oldest rapid transit system in the Americas behind Boston. It’s also the second-largest rapid transit system in the U.S. behind New York.

I’m loving public transport, looking around at passengers and neighborhoods we pass while Jay has his head in a book. I look closer and it’s a history on Chicago’s underworld named The Outfit.

I ask how the book’s going.

Jay’s eyes shine like an excited kid. “Dahhhhhhm (my nickname is Dom), this book is dope! Did you know, when Capone got busted it wasn’t for the kidnapping he organized? The police didn’t care about that, but got him for not paying taxes on the ransom money he got from it.” He continues on with beaming pride about the history and strict gang/police structure in Chicago back in the early 1900s.

Jay further explains how gangs in his neighborhood follow rules in today’s Chicago. Each move has a reason and has been approved. I realize I’m listening to history translated to tradition.

The sign is an important part of the decision process.

But if tradition starts there or with sports or with something else, it’s best felt (OK, “tasted” I guess) with Chicago food. Ask locals about it. Eat it. Then ask more locals about it. Where to start, you ask? Go on a Chicago-style hot dog search – or “red hots” as they call them. Start anywhere, really, because the city is littered with Vienna or Kosher hot dog stands. Yeah, they're so serious about the hot dog that signs showing the meat used are outside.

But let’s back up: why “red” dogs? I’m confused, especially because a Chicago-style dog isn’t eaten with ketchup… at least by a real Chicagoan.

As I order my second red dog (this time at Portillo’s, after stopping at Polk and Western first), “Um, can I get that with some ketchup please?”

Check out the reply in the video…it’s pretty simple.

But don’t stop there, wherever you’re eating your red dog. Ask a server where you can find another great Chicago-style dog – they’ll tell you about their other favorite joint, probably pretty close by too. So goes the red dog adventure times.

And the answer to why they’re called ‘red’: no one I met knows…or seems to care really. It's all about proud tradition.

Tasty sidenote: any Chicago food hunt is incomplete without mentioning deep dish – it really lives up to the hype. And it only needs a three-ish sentence paragraph. Eat it.

There are heaps of things to do in Chicago for a visitor and local alike. But please try to find your Patty Ohio, enjoy the not-so-elevated-any-longer Chicago El, get in touch with the Capone clique (perhaps take the Mob Tour), and consume copious amounts of food while asking locals about what you’re eating and where you should go to next.

Oh and about that Ken Caminiti: it’s apparently made with steroids and GHB, per Johnny Golf Shoes. But that didn’t stop him from concocting an extra one for himself to go along with mine.

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A not-so-elevated El train stop, Chicago.
A not-so-elevated El train stop, Chicago.

“Tell Johnny Golf Shoes that you want a Ken Caminiti, and that Patty Ohio sent you,” the server at Big Bowl tells me.

Am I seriously being told to go to a random bar with this message? Yes I am. Am I going? Definitely. And yeah, I’m in Chicago. Patty Ohio is showing me one of the three things Chicagoans love: insider connections. The other two you ask? Their history and traditions.

One of the city's proud traditions: the Chicago-style dog.

But let’s get back to the beginning of the trip. I’m with my Chicago buddy Jay riding the El train (the “el” is short for “elevated”) headed to his mom’s home on the West Side. This train first ran its course in 1892 – part of it, anyway – making it the second-oldest rapid transit system in the Americas behind Boston. It’s also the second-largest rapid transit system in the U.S. behind New York.

I’m loving public transport, looking around at passengers and neighborhoods we pass while Jay has his head in a book. I look closer and it’s a history on Chicago’s underworld named The Outfit.

I ask how the book’s going.

Jay’s eyes shine like an excited kid. “Dahhhhhhm (my nickname is Dom), this book is dope! Did you know, when Capone got busted it wasn’t for the kidnapping he organized? The police didn’t care about that, but got him for not paying taxes on the ransom money he got from it.” He continues on with beaming pride about the history and strict gang/police structure in Chicago back in the early 1900s.

Jay further explains how gangs in his neighborhood follow rules in today’s Chicago. Each move has a reason and has been approved. I realize I’m listening to history translated to tradition.

The sign is an important part of the decision process.

But if tradition starts there or with sports or with something else, it’s best felt (OK, “tasted” I guess) with Chicago food. Ask locals about it. Eat it. Then ask more locals about it. Where to start, you ask? Go on a Chicago-style hot dog search – or “red hots” as they call them. Start anywhere, really, because the city is littered with Vienna or Kosher hot dog stands. Yeah, they're so serious about the hot dog that signs showing the meat used are outside.

But let’s back up: why “red” dogs? I’m confused, especially because a Chicago-style dog isn’t eaten with ketchup… at least by a real Chicagoan.

As I order my second red dog (this time at Portillo’s, after stopping at Polk and Western first), “Um, can I get that with some ketchup please?”

Check out the reply in the video…it’s pretty simple.

But don’t stop there, wherever you’re eating your red dog. Ask a server where you can find another great Chicago-style dog – they’ll tell you about their other favorite joint, probably pretty close by too. So goes the red dog adventure times.

And the answer to why they’re called ‘red’: no one I met knows…or seems to care really. It's all about proud tradition.

Tasty sidenote: any Chicago food hunt is incomplete without mentioning deep dish – it really lives up to the hype. And it only needs a three-ish sentence paragraph. Eat it.

There are heaps of things to do in Chicago for a visitor and local alike. But please try to find your Patty Ohio, enjoy the not-so-elevated-any-longer Chicago El, get in touch with the Capone clique (perhaps take the Mob Tour), and consume copious amounts of food while asking locals about what you’re eating and where you should go to next.

Oh and about that Ken Caminiti: it’s apparently made with steroids and GHB, per Johnny Golf Shoes. But that didn’t stop him from concocting an extra one for himself to go along with mine.

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4S Ranch Allied Gardens Alpine Baja Balboa Park Bankers Hill Barrio Logan Bay Ho Bay Park Black Mountain Ranch Blossom Valley Bonita Bonsall Borrego Springs Boulevard Campo Cardiff-by-the-Sea Carlsbad Carmel Mountain Carmel Valley Chollas View Chula Vista City College City Heights Clairemont College Area Coronado CSU San Marcos Cuyamaca College Del Cerro Del Mar Descanso Downtown San Diego Eastlake East Village El Cajon Emerald Hills Encanto Encinitas Escondido Fallbrook Fletcher Hills Golden Hill Grant Hill Grantville Grossmont College Guatay Harbor Island Hillcrest Imperial Beach Imperial Valley Jacumba Jamacha-Lomita Jamul Julian Kearny Mesa Kensington La Jolla Lakeside La Mesa Lemon Grove Leucadia Liberty Station Lincoln Acres Lincoln Park Linda Vista Little Italy Logan Heights Mesa College Midway District MiraCosta College Miramar Miramar College Mira Mesa Mission Beach Mission Hills Mission Valley Mountain View Mount Hope Mount Laguna National City Nestor Normal Heights North Park Oak Park Ocean Beach Oceanside Old Town Otay Mesa Pacific Beach Pala Palomar College Palomar Mountain Paradise Hills Pauma Valley Pine Valley Point Loma Point Loma Nazarene Potrero Poway Rainbow Ramona Rancho Bernardo Rancho Penasquitos Rancho San Diego Rancho Santa Fe Rolando San Carlos San Marcos San Onofre Santa Ysabel Santee San Ysidro Scripps Ranch SDSU Serra Mesa Shelltown Shelter Island Sherman Heights Skyline Solana Beach Sorrento Valley Southcrest South Park Southwestern College Spring Valley Stockton Talmadge Temecula Tierrasanta Tijuana UCSD University City University Heights USD Valencia Park Valley Center Vista Warner Springs
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