EATING CHICAGO: where to eat in the Windy City

Chicago. Land of Obama, towering skyscrapers and the reigning World Series winning Chicago Cubs. Home to awe-inspiring architecture, world-class museums and one of America’s most dynamic food scenes. It’s rare that such a big city can still feel both spacious and approachable at the same time. But America’s 3rd largest city manages to do just that thanks in large part to the expanse of Lake Michigan, an ample amount of green spaces and the friendly, straight-talking locals.

Food-wise, it’s not just about Deep Dish Pizza, Hot Dogs & Italian Beef sandwiches in Chicago. Look beneath the Windy City’s stereotypical specialities and what you will find is a food scene that spans everything from old-school diners to 3 Michelin star restaurants, rivalling that of New York & San Francisco in diversity and quality.

Here’s a round up of 12 of our favourite eats from our recent trip – starting with our pick of Chicago’s flag-bearer dishes through to the best of the higher end restaurants we came across.


Al’s #1 Italian Beef

The moistest, most succulent of Italian Beef. Full gravy dip to soak up all that goodness. Topped off with sweet and hot Giadiniera peppers. I’ve been dreaming of having this sandwich ever since seeing Adam Richman chow down on it on Man vs Food many years ago. And boy did it live up to its billing. This flavour bomb goes straight into my world sandwich hall of fame.

Giordano’s Deep Dish Pizza

Prepare yourself for cheese & toppings for days at Giordano’s – my favourite of all the Deep Dish Pizza joints we tried. The crust here at Giordano’s is what sets it apart for me – crispy, flaky and surprisingly light, it’s the perfect medium to carry all that cheesy goodness.

Jim Original Hot Dog Stand @ Maxwell Street

The aroma of grilled onion’s & sausages emanating from this 24 hour, 70+ year old Chicago institution is euphoria-inducing! The original of Maxwell Street’s hot dog stands, there’s the choice of their signature Polish or classic Chicago Vienna brand dogs – both grilled to perfection with that firm, juicy ‘snap’. Remember to ask for caramelised onions, zingy relish & mustard, always!


Few places come more classic Chicago than Portillo’s. Order yourself some of their signature hot dogs or Italian Beef and soak up those vintage diner vibes.


Hit up Rick Bayless’ casual sandwich, soup & taco eatery in River North for some bold, comforting Mexican flavours. Their Suckling Pig Conchinita torta, smoky Short Rib Chile soup & salsas were all superb. Fantastic Churros too – great crunch and top-notch chocolate.


Seafood Gumbo in a Chinese restaurant? That’s how Dolo in Chicago’s Chinatown rolls! Their house speciality, a 5 lb XL bathtub of the freshest crabs, clams, crayfish & prawns cooked in a spicy Cajun-style broth is a seafood lover’s dream come true. Finger-licking-licious stuff! There’s solid Cantonese specialities and Dim Sum at lunchtimes too for those who’d rather stick to the Chinese options.

Girl & the Goat

Reigning Iron Chef Stephanie Izzard’s flagship West Loop restaurant serves up some of the most delicious, globally inspired cuisine I’ve come across anywhere. Their Duck Tartare dish with gooseberries, pickled mushrooms, gochujang mayo & duck fat lavash bread is one of the best things I’ve eaten in 2017 so far. The flavours were bold yet totally harmonious. So many different influences from round the world and textural components at play! Top marks for style, service and booze selection too. Fully deserving of its hype.


The inspired Mediterranean small plates at this buzzing West Loop favourite draws the crowds in all day all night. It was packed even after 11pm on a school night when we stopped by for late night supper! Their signature Medjool dates, stuffed with Chorizo, wrapped in bacon and served with spicy piquillo pepper sauce were sensational. Top wine list too, with bottles curated from all round the world to wash down the top-notch food.

Duck Inn

Head down south to Stockport to dig into the Duck Inn’s signature Rotisserie Duck – served complete with duck fat potatoes, baby kale, citrus & heirloom radishes. Hearty, honest cooking of the highest order! Their Duck Fat Dog is also a must. The depth of flavour in the duck and beef sausage is just incredible. Cooked in duck fat, its smoke-kissed skin had a great snap to it… the house-made relish and pickles on the top cut through all the richness beautifully. BEST. HOT DOG. EVER.

Mon Ami Gabi

There’s Gallic flair and old school French bistro vibes galore at Lincoln Park’s Mon Ami Gabi. The star of the show here is their 22 oz USDA Bone-in Rib-eye steak, served with mega moreish truffle béarnaise and their cracking pomme frites – possibly the tastiest fries I’ve come across anywhere.

Shakou Park Ridge

Take the trip out to Shakou Park Ridge in Chicago’s outer suburbs for a truly exquisite modern Japanese Omakase meal by Head Chef Min. Expect fresh produce, spot on seasoning and creativity aplenty. It was really refreshing to see global influences like pico de gallo and gochujang incorporated seamlessly into the contemporary sushi here. Their Uni ‘bibimbap’ and Amberjack Nigiri with nori, sesame oil and wasabi salt were the highlights of a marvellous meal!

El Ideas

Modern American cuisine meets BYOB Supper Club at this 1 Michelin star gem located off the beaten track in Chicago’s Douglas Park neighbourhood. Guests are encouraged to mingle, roam around the open plan space and watch the chefs in action. Expect fireworks and ingenuity throughout their ever-changing contemporary tasting menu. I can’t stop thinking about their signature French Fries with ‘exploding’ liquid nitrogen ice cream and 75 day aged Beef Fillet with smoked potatoes. A truly unforgettable experience!