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GMG 40: Lupe Fiasco’s Guide to Chicago

By Adam Valeiras on August 1, 2012


GMG 40: Lupe Fiasco’s Guide to Chicago

Chicago can be a tough town. The streets are mean, the winters rough; the Cubbies are a lost cause and Da Bears didn’t make the playoffs. Unless you’re a tuned-in native or a writer for Lonely Planet, a day in Chi-town can very easily result in hours spent meandering between Grant Park and Pizzeria Uno. Don’t do that. Rather, let us present a new resource from a homegrown talent: rapper, producer, business executive and, naturally, Chicago local and lover (and columnist!), Lupe Fiasco.

Fresh off finishing up the final touches on the long-awaited Lupe Fiasco’s Food & Liquor II: The Great American Rap Album, Part 1, out this fall, Lupe took the time to reveal a few of his hometown’s lesser-known secrets. (He even fessed up the location of his favorite parking spot. Nuts!) So whether you’re in town for a festival weekend, some business interactions, a ball game or the city’s esteemed selection of historical and art museums, let Lupe tell you about his Chicago. And stay the hell away from Uno, alright?

Photo by Matt Reeves/Darkroom Demons


Best Waiter
Mohammed at Gibson’s

An all-around wonderful man at my favorite restaurant in Chicago. This is a place where the food is awesome and the people who run the joint are even more awesome. Moe is top-shelf class all the way. Best waiter in the world. He might even bring food from another restaurant if that’s what you really wanted. [1028 N. Rush Street]

Best Newspaper Article
My Column “Rapper’s Delight” in the Chicago 

I mean, why not? Best of both worlds. My words in the hometown paper; what more can you ask for?

Best Guy To Show You Around Town
Lenny Mancari

The unofficial mayor of Chicago. Knows everybody, not everybody knows him, but if you do know him you’re definitely a somebody. Bada bing, bada boom.

Best Place To Park Legally On The Street Downtown Without A Paying Meter
East Superior Street Between Neiman-Marcus and Saks Fifth Avenue For Men


Best Caramel Cupcake
Brown Sugar Bakery

Addiction is a meal best served with caramel on it. The absolute best of the best. [328 E. 75th Street]

Best Harold’s Chicken
Unfortunately It’s Closed, But It Would’ve Been the One on Stony Island around 83rd Street.

’Twas a sad day when the doors closed. But trust me when I say just the mere memory of the fried chicken in this particular Harold’s puts all the rest to shame.      

Best Place To Pick Up A Copy Of Adbusters
Quimby’s Bookstore

You need leftist literature? They got it. Need local authors by the boatload? They got it. Need more indie zines than law should allow? They got it. [1854 W. North Avenue]

Best Gas Station To Get Green Apple Now & Laters
The Citgo out in Sauk Village

Yeah, it’s that serious. And yes, I really spent months tracking this place down for one thing and one thing only: Now & Laters. [2393 E. Lincoln Highway]

Best Organization Trying To Fight Chicago’s Skyrocketing Murder Rate
Cease Fire

The city’s murder rate is climbing by the day. So as you read this, know that Cease Fire and more organizations like it are doing their best to curb youth violence and hopefully save a life. God bless ’em.

Best Place To Get Clothes When Money Ain’t a Thang
George Greene on Oak Street

The place where luxury swagger is on tap and on sale. The guys who run the place need their own TV show. You’ll see when you get there. Oh yeah, bring the credit cards! [49 E. Oak Street]

Best Place To Get Clothes When Money Is Certainly a Thang
Madison & Pulaski Business District

For the budget ballers and fiscally responsible, just hit up the crossroads of the hood and I’m sure you’ll find what you need. Prepare to haggle.  F

Coastline and license plate photos by Lupe Fiasco