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O THE LOOP


WHY GO? The beating heart of Chicago, The Loop is the city’s downtown core, with glossy mirrored skyscrapers jutting above historic landmarks, lively restaurants and swish rooftop bars. It’s here that you’ll find the city’s famous Theatre District, the Chicago Riverwalk and Millennium Park – a sprawling green space that hosts regular concerts, with a buzz that extends well beyond the working week.


WHAT TO DO Start with a stroll through the park, home to The Bean, a shiny metal marvel by artist Anish Kapoor, where you can snap your morphed reflection in front of the city skyline. If clients are here in summer, suggest staying on into the evening for one of the regular free outdoor concerts and film screenings put on as part of the Summer Music and Film Series. Next to the park sits the Art Institute of Chicago, which was founded in 1879 and features one of the largest art collections in the US, including works by Picasso, Van Gogh, Warhol and Monet, alongside Chicagoan artists. Then head to the Chicago Riverwalk, where


restaurants and bars line a buzzing waterfront, or hop on a boat from Navy Pier to take in the skyline from a different perspective. Great views can also be found from the Skydeck at Willis Tower (pictured), once the tallest building in the world. Go at night to see the city lights twinkle from a glass- floored platform, or try chic spot Cindy’s Rooftop for food and cocktails overlooking Millennium Park.


DESTINATIONS CHICAGO | THE US


LITTLE VILLAGE


WHY GO? The ‘Mexico of the Midwest’, Little Village became the main entry point for Mexicans arriving in Chicago in the 1990s and, today, it’s one of the most vibrant and colourful spots in the city.


WHAT TO DO Start at the Little Village Arch, a terracotta archway built in 1990 to recognise the area’s Hispanic community. Amble to the Nuevo Leon Restaurant to see the huge, midnight-blue Day of the Dead mural, then stop at Dulcelandia (pictured) for an explosion of colour, with artisanal sweets stacked beneath bright piñatas. Stop at the family-run Taqueria Los Comales for pork-filled tacos al pastor and milky drink horchata, then duck into Artesanias Elena to browse traditional Mexican crafts. If you’re here on a summery Saturday, visit the Mercado de Colores, where streets teem with food vendors and live music, then end with a visit to Osito’s Tap, a speakeasy serving Latin-inspired cocktails.


² travelweekly.co.uk 13 NOVEMBER 2025 37


PICTURE: Ranvestel Photographic; Powell Photography/Choose Chicago


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