Patrick Hanlon of The Gastro Gays takes a delicious bite out of Chicago, listing some of the must-see (and must-taste) spots of Chi-town.
Being driven around downtown Chicago in one of those iconic, yellow school buses and eating the day away at different pizza stops might just be the most American experience I’ve ever had.
The Windy City is the home of deep dish, so I’m one of a gang of 20 spending their Saturday morning buckled up like kids on a school trip to amble around Chicago trying different pizzerias.
From "tavern-style" cut into little squares served on napkins at Polish-Italian pub Flo & Santos in South Loop to thin crust, leopard-spotted pies at nu-wave artisan Coalfire in West Town, pizza means big business in 'The Second City’ with lots of different styles at play.
I’ve taken part in my fair share of food tours through the years but seeing a city through its pizza culture is one of the more niche ways I’ve explored a city as a first-timer.
Chicago Pizza Tours (chicagopizzatours.com) has been running since 2010 and the school bus is a novel way to get around, with history and explainers punctuating the route and six tastings across four different stops, from Pizano’s, styled like something from Goodfellas, to the neighbourhood slice shop Bartoli’s.
Stringy, mozzarella cheese pulls get more epic with each stop as most places offer their slightly different takes on ‘Deep Dish’. A style synonymous with America’s "Second City ", these are pan-baked, high-sided pies with a shortcrust-like dough filled ‘upside down’ –– chunkier tomato sauce sitting above a generous cheese layer.
As a three-hour tour this not only requires appetite and enthusiasm but stamina. Make sure to clear your afternoon of activities, a nap should be mandatory afterwards.
Chicago is a city primed to explore being led by the tastebuds. The Bear has been FX’s breakout award-winning drama of recent years, which follows the struggles of a family-run sandwich shop in River North with Jeremy Allen White in the lead role as Carmy, a hot-headed but razor-focused fine-dining chef, alongside Ayo Edebiri - Ireland’s very own adopted daughter - as his pure-hearted sous, Sydney.
The show, while being brilliantly-written but often blood pressure-spiking, has shone a light on Chicago’s culinary credentials to a wider audience.
Alongside deep dish another must-try in the city is Italian beef, a sub roll lavished with slow-cooked, gravy-dunked beef in thin slices served with or without cheese and spoonfuls of giardiniera, a hot and sharp condiment of chopped celery, carrot and peppers pickled, then stored in oil. It is a uniquely Chicago thing, originating from Italian immigrants who worked in the city’s stockyards.
This is the sandwich, and the casual shops in which it is found across Chicago, which sets the scene for The Bear storyline. The fictional ‘The Original Beef’ in the show is based on an actual business, Mr. Beef, a staple of the River North sitting on Orleans for 45 years.
An unassuming joint with characterful service, the walls are adorned in autographed portraits of famous faces who have come through the doors, from Keith Richards and Jay Leno to Christopher Walken. It is not dissimilar from a Dublin icon, Leo Burdocks, which boasts its own wall of fame from across a 110-year history in Christchurch.
If a sandwich were to ever be declared "succulent", this is the one. The beef flavour is intense, the giardiniera is hot, sharp and lip-puckering while another layer of ‘sweet’ peppers, all soft and slippery, brings balance. Getting it ‘dipped’ is an optional step, where the entire sandwich gets baptised in warm beef jus before serving.
The sub emerges saturated, rendering it a messy eat but most definitely leaves you licking your fingers. Eating it at source feels like an act of devotion.
Right along Chicago’s ‘Magnificent Mile’, the main commercial strip of the city, The Gwen (thegwenchicago.com), is your ideal base. Part of Marriott’s Luxury Collection with sleek, art deco stylings, its location right off Michigan Avenue is perfect for those who want to hit the boutiques. Located near the Chicago River, there’s no better way to see the city and its unique architecture than on the water.
For over 30 years the Chicago Architecture Center has partnered with Chicago’s First Lady Cruises (cruisechicago.com) to offer 90-minute guided boat tours aboard its fleet of river cruises.
Chicago is remarked as the birthplace of the modern skyscraper and its eclectic array of buildings and styles is captivating, especially witnessed from the water while sipping a hot toddy from the on-board bar.
To truly take in the dimensions of the city, it is also worth ascending from its waters to its heights. The 110-storey Willis Tower (formerly Sears Tower) is Chicago’s tallest building and was the world’s tallest for 25 years until the turn of the Millennium.
Its SkyDeck observation floor (theskydeck.com) on the 103rd floor offers a unique vantage point and photo opportunities, just check the weather forecast beforehand or risk being met with a wall of thick cloud and 0% visibility like I was.
Another opportunity to ascend and take in a breathtaking city vista is 360 Chicago (360chicago.com), an observation deck set 1,000 feet above the city on the 94th floor of the John Hancock Building. Coordinate your timings to sip sundowners from the bar as the sun sets over the city and Lake Michigan.
If the buzz of Downtown isn’t your thing, retreating to Wrigleyville - the North neighbourhood anchored by Wrigley Field ballpark - might just be your bag.
For sports fans, take a tour or catch a baseball game at the home of the Chicago Cubs, for comedy lovers don’t miss a show at the iconic improv institution that is The Second City (secondcity.com) and another great spot to base yourself is the modern and plush surrounds of the Tribute Portfolio Hotel Zachary (hotelzachary.com).
If The Bear convinced you to take a bite out of Chicago you could easily spend a trip simply eating your way around Chi-town where the dish is deep and the beef sandwiches come saturated –– and the flavour of both last long after you have waved goodbye to the Windy City.
Patrick Hanlon was a guest of Choose Chicago choosechicago.com
