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Windy City whirlwind

Irish Sunday Mirror

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June 22, 2025

Packing in top tours, Niamh Kirk is swept away by Chicago

With its blockbuster movie skyline, fabulous food options and notorious crime history, Chicago has plenty to enthrall curious city-breakers. And there's every type of tour led by clued-up locals to whisk time-pressed travellers straight to the best bits.

Fancy sampling the best deep-dish Chicago pizza? Want to see the church where mob funerals took place? How about gazing at one of the world's most diverse and shapeshifting skylines while cruising the Chicago River?

Be it by bike, bus, boat or on foot, there are routes carefully crafted by experts and insiders to let the Windy City blow visitors away with the stories of the people who put it on the map.

Chicago is one giant eating adventure with endless famous foods to tick off. With limited time to seek out the prize picks, I took the Tacos and Tequila street-food tour of Pilsen, one of Chicago's most colourful and culturally rich neighbourhoods.

The three-hour tour, run by Chicago Food Tours Company and led by a local guide, spreads out across 1.5 miles taking in the very best Mexican drinks and dishes.

For €70 you'll get to make your own tamales - spicy fillings wrapped in corn dough - sample steak tacos, Mexican pork and the most irresistible churros dipped in icing sugar and chocolate, all while admiring the many murals inspired by Mexican culture in the neighbourhood. You'll also get the all-important lowdown on the best spots to sip margarita cocktails. My kind of town...

I also couldn't resist delving into its dark underworld with Chicago Crime Tours. The two-hour, €35, bus tour takes you to some of the most infamous crime scenes, landmarks and mobster hangouts, including the site of the Valentine's Day Massacre in 1929.

Plus you'll get to hear the true crime stories of Al Capone, The Untouchables, Frank 'The Enforcer' Nitti, and the Prohibition era along the way.

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