I spent 96 hours eating my way around Chicago — it’s more than deep-dish

I spent 96 hours eating my way around Chicago — it’s more than deep-dish

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I spent 96 hours eating my way around Chicago — it’s more than deep-dish
Author: Joy Anokwuru
Published: Feb, 05 2025 07:00

If you love food, I’m here to tell you: Chicago is it. The home of deep-dish pizza, Italian beef and Chicago-style hot dogs (no ketchup allowed), I spent four days eating my way around the Windy City, a place that’s comfort grub personified. This culinary scene may be more under-the-radar than New York or Los Angeles, but it’s time it receives the recognition it deserves. Illinois’ largest city is a melting pot of cuisines — Italian, Mexican, Chinese, Polish, and Greek. So diverse, it’s often said that when you go out to eat, you’ll forget you are in America. Let’s dig in.

Image Credit: Metro

Pilsen, regularly voted one of the coolest neighbourhoods in the world, is rich in Mexican history and Mexican food. A good place to start is the Taco’s and Tequila food tour (from $85), where I drank the best margarita of my life at Michelin-star 5 Rabanitos. For a reasonable $11.50, the House Margarita Cazadores Reposado comes laden with tequila, orange liqueur, fresh lime juice, simple syrup, and a dusting of something that looks like Peri-Peri salt. A great remix of a classic.

Image Credit: Metro

Speaking of drinks, move over iced coffee and make way for horchata. Made with rice milk flavoured with cinnamon and sugar, it has replaced all other iced drinks in my affections. Horchata is my new Roman Empire. At Carnitas Urapas, I tried deep-fried pork belly ($7.50), which changed my mind about pork in general. Satisfied with my Mexican gastronomic success, I stopped by Perilla, a Korean-American steakhouse inside the L7 by Lotte Hotel. Two dishes are unmissable: the Korean fried chicken ($26) and monkey bread ($12), a sweet, sticky pastry served with honey butter for breakfast and dessert.

Image Credit: Metro

Of course, no trip to Chicago is complete without a deep-dish pizza — at Giordano’s, one of the city’s most iconic Italian chains, it’s thick, cheesy and moreish, worlds away from anything you’ll find in the UK. For all my #cheeselovers out there. Go to #chicago and get yourself a #deepdishpizza and thank me later. #foodie #foodtok #foryou #fp #foryou. Chicago is heaven for sweet teeth. In Pilsen, I visited a panaderia, a Mexican bakery where you’re handed a tray and instructed to choose what you like. I went for Mexican churros slathered in cinnamon sugar.

Image Credit: Metro

Molly’s Cupcakes, an award-winning bakery and winner of Cupcake Wars on The Food Network, blew my mind. Inventive flavours include ‘Smore’s’ and ‘Cake Batter’ ($4.25), which is, as it suggests, a cake filled with cake batter. Another standout is the award-winning ‘Ron Bennington’ ($4.25), a chocolate cake with peanut butter filling, chocolate ganache and crushed butterscotch topping.

Last but by no means least, I found room to squeeze in the Grand Rocher dessert at Hawksmoor, an upscale chain with restaurants in New York, London and Dublin as well as Chicago. The Grand Rocher is a beast: enormous, rich, and dripping in flakes of edible gold. What more could you want?. I visited in September, when the weather was around 23°C, but locals warned me about winter when temperatures can plunge to -22°C.

If you can brave the cold, you’ll find cheaper hotel and flight deals, but autumn and spring are the best times to visit for milder weather and fewer crowds. There’s plenty to do in Chicago while you wait for your next meal. Work off some calories on a bike tour with Bobby’s Bike Hikes, which traverses the city’s many neighbourhoods and the banks of Lake Michigan. Float along the Chicago River on The Architecture Cruise, where you’ll learn about the city’s history in the shadow of towering skyscrapers. Challenge your fears by walking the glass floor of the Sears Tower, or watch the Chicago Bulls shoot hoops for some live-action sport at the United Center.

Laugh the night away at a Second City comedy gig, or chug a beer at a tailgate at Chicago’s iconic Soldier Field if football’s more your scene. For something a little different, Chicago Magic Lounge delivers an intimate glimpse into the world of illusion. No trip to the Windy City is complete without going full throttle into the jazz and blues scene: some of the best are Green Mill Jazz Club in Uptown, and Buddy Guy’s Legends.

The perfect antidote to a day (or four) of eating. Where I stayed. L7 by Lotte Chicago, a new hotel inspired by Korean hospitality with face masks and a yoga mat in your room. It’s in an unbeatable location, close to Millennium Park, The Art Institute of Chicago (ranked the city’s no.1 attraction) and most importantly, viral cookie sensation, Crumbl. After trying the chocolate chip flavour, I concluded that UK desserts cannot, and will never, compare.

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