& Fifteen quintessential Chicago experiences
If you asked me about Chicago six months ago I would’ve had two things to say about this city: deep-dish pizza and the Chicago Bulls. But when your first few hours in a place involves balmy temperatures, five-dollar negroni slushies, a smoky fried chicken sandwich and the outdoor courtyard at Parsons Chicken and Fish—you can guess you’re in for a pretty good time. After five days of investigating this city’s swoon-worthy vista and thriving culinary scene, the tagline on a trendy gift shop tea towel summed up my trip pretty well … ‘Things to do in Chicago: eat, eat again, continue eating, see ‘the bean’, resume eating …’
- Chicago Style Deep-Dish Pizza – Some call it a pie, some a cheese lasagne, but whatever you call it, tackling the extravagance at Giordano’s is no easy feat. After ditching the first packed-out location, we were welcomed to the second with a mere 45-minute wait. Thankfully ignoring the advice of the waitress, we refrained from appetisers and opted for the ‘small special’. Perched on its own table stand, the deep bread-like crust encased a canyon of stringy cheese, crowded with pork fennel sausage, green peppers, onions and mushrooms, all smuggled beneath a chunky tomato sauce and help-yourself Parmesan and chilli. One piece was absolutely enough. And the wait? … worth it.
- A Dash of Culture – Several selfies later we were positively wooed by the mirrored steel surface of the aforementioned ‘bean’, the iconic Cloud Gate sculpture housed at Millennium Park. Wandering through the expansive public parks, we sheltered from whistling winds and spent several enthralling hours at the Museum of Modern Art Chicago. A further meander, this time by bike, had us riding parallel to the teal waterfront of Lake Michigan towards the Field Museum of Natural History and a rather daunting dinosaur skeleton.
- Pie and Biscuits – We were tempted by several different graham-crusted pie combinations at Bang Bang Pie and Biscuits from key lime to orange-blossom honey custard and an oatmeal ginger pear number. With a few days up our sleeves, I justified the acquisition of all three. The Bucktown neighbourhood joint served sweet American pies with pizzazz and somehow a fudgy ginger molasses cookie made its way into my mouth that day and my life has been changed for the better.
- Skyscraper Views – Thanks to intel from a resident local, we found ourselves 96 storeys high up the John Hancock Centre observing an unrivalled view of the Illinois horizon. We rewarded our ear-popping elevator climb with a locally-brewed Goose Island wheat beer in the Signature room, with no tourist lines to contend with.
- Donuts – Forced indoors by soggy Chicago streets, our donut trawl began with a lemon pistachio old fashioned from Stan’s Donuts & Coffee. I’m still not sure whether it was the sweet dough ring itself or the rainbow display of KitchenAid mixers that won me over here. But there was no question we were ordering the carrot cake donut from Firecakes: moist crumb, cream cheese frosting, orange zest and candied toasted walnuts. I only take my carrot cake in donut form from now on. Perched in Logan Square Park we devoured a pandan sugar-coated donut filled with passionfruit curd from the Bakery at Fat Rice—a self-prescribed funky Asian bakery where ‘fusion’ looks like a Ceylon snickerdoodle cookie with salted yolk custard and a Macau rice crisp where marshmallow, pork floss and seaweed meet fish sauce caramel. Equal parts quirky, strange and undeniably delicious.
- Coffee – Several caffeination moments involved cortado’s (a strong, baby flat white) at suburban roaster Ipsento coffee and single origin filter brews from nationally recognised Intelligentsia, with locations dotted throughout the city. Though it was at Printers Row Coffee Co where we became acquainted with (and enjoyed) the millennial milk of the moment—‘Oatly’ oat mylk. In the West Loop, Sawada coffee served an intriguing brew by way of a military latte, where high-grade Japanese matcha met a shot of espresso.
- BBQ Meat – Sharing a space with Sawada coffee we found Green Street Smoked Meats dishing up a monumental selection of smoked proteins. Highlights were the chicken leg, saucy pulled brisket and an innocent pottle of creamy elote-style corn with a kick of spice and hint of lime. It was thanks to a tip-off from the crew at Mr Pickles in Hamilton that I discovered a glorious plate of pecan smoked BBQ ribs with garlic buttermilk potatoes. The small restaurant, Giant, is making big waves in the Chicago dining scene and stealing hearts (possibly just mine) with its king crab saffron tagliatelle.
- Dinner and a Show – Nabbing a last-minute seat to Hamilton (and a better deal than most NYC shows) at the CIBC theatre was a brilliant result. We preluded the award-winning Broadway performance with a Mediterranean meal at Ē Involving the revelatory combination of hummus, lamb ragù, spicy harissa and za’atar flatbread (no mashed spud in sight) and was educated about the joys of adding cracked pepper to Tanqueray gin.
- Diner Breakfast – An obligatory post-show breakfast was consumed at all-day eatery Little Goat Diner, part of the ‘Goat’ empire run by renowned female chef Stephanie Izard of Chicago. Serving diner classics with a modern twist, the diverse table spread involved blueberry pancakes with vanilla malt butter, a Korean inspired bibimbap vegetable bowl and a triumphant and considerably sized cinnamon bun.
- Chicago Architecture Tour – It only took 90 minutes to make me fall in love with buildings, specifically the architectural gems along the riverside. Aboard the Chicago Architecture Foundation River Tour, our dynamic guide shared an unparalleled knowledge and a memorable soundbite about how “buildings are a way that generations speak to each other”. It probably comes as no surprise that the corn cob lookalike Marina City buildings and the ex-meat works were personal favourites.
- Suburban Eats – It was a single slice of crusty oat porridge bread with briny butter that drew me in at Cellar Door Provisions. This quaint eatery with a communal character and soulful service delivered thoughtful, vegetable-laden, ferment-focused dishes, including an agnolotti nettle pasta filled with farmers cheese and whey broth. My only regret was not ordering a slice of their infamous silky custard quiche with its own global following.
- Burger and a Shake – With a choice of three items, ordering at Small Cheval was possibly one of the best and most straightforward decisions of the trip. Doubles are the standard here, served on red gingham paper with golden skin-on fries. It tasted exactly as a cheeseburger should. With piquant pickles, American cheese and a fluffy golden bun. But it was the vanilla bean flecked thick shake that stole the show—essentially gourmet soft serve in a cup.
- Not So Hot Dogs – On a hunt to find the best Chicago hotdog we undertook some serious Uber driver research and found ourselves at Portillo’s Hot Dogs. The themed restaurant should have given it away. But years of fame and following couldn’t save its soggy white bun, oddly fluorescent pickle, watery tomatoes and mediocre sausage. Sorry Chicago locals, but it’s a no from me.
- Elevated City Rides – Riding the elevated tram around the inner city ‘Loop’ was a total highlight, zooming past Macy’s department store and exercising my newfound appreciation for architecture. The ultimate tip of the trip was a sneak peek into the grandiose lobby at the Palmer House Hilton Hotel where it felt like we’d walked straight onto the set of a James Bond film. Another holiday peak was unlocking the city-wide Divvy bikes and cruising along the raised Bloomingdale trail—a prime example of beautiful, functional, public spaces that define a city.
- Pan Pizza – Striding through suburbia to finish the trip with a slice of Pequod’s famous Michelin star pan-style pizza was worth every second of pre-airport panic. Particularly when 30 (stressful) minutes later a piping hot, spongy, yeast-laden dough arrived on my lap covered in gooey mozzarella, glistening slices of pepperoni and encased in a blackened cheese-crusted halo. It was heaven in a styrofoam box and an edible memory I’m unlikely to forget.
What stood out across the plates of this place was a playfulness in flavour and a commendable execution of the often ‘trashy’ American classics. At the start of spring, this place was pretty hard to fault. And perhaps the most magic and surprising element of the windy city were its friendly inhabitants, each exuding a warm generosity and hospitable charm. I’m going back, just armed with pants that give a little!
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