Why Chicago is the USA's greatest city break

20 October 2025

It's official: Chicago is a city that just keeps getting better. For an incredible ninth year in a row, readers of Condé Nast Traveller have named it the ‘Best Big City in the U.S’. As if that wasn't enough, it also scooped the 2025 Travel Noire Award for ‘Best Stateside Vacation’. These accolades confirm what savvy travellers have known for years: Chicago offers a city break experience that’s hard to beat, blending iconic sights with a friendly, down-to-earth atmosphere. It’s a city of soaring skyscrapers, world-class museums, and a food scene that constantly innovates, making it a perfect destination for any time of year.

Why Chicago is the USA's greatest city break

Architectural marvels and culinary stars

One of Chicago’s most striking features is its skyline. A boat tour along the Chicago River is the best way to appreciate the sheer scale and beauty of its architecture. Guides will point out landmarks like the Wrigley Building and Tribune Tower, explaining how the city became a blueprint for modern urban design. Beyond the buildings, Chicago is a city of neighbourhoods, each with its own distinct character. You can explore the galleries of River North, the boutique shops of Lincoln Park, or the historic streets of Old Town.

The city’s food scene is equally impressive and was praised by Travel Noire for its celebration of creativity. From Michelin-starred dining to the iconic deep-dish pizza, there's something to satisfy every palate. You could spend your days trying classic Chicago-style hot dogs or exploring the diverse culinary offerings at food halls like Time Out Market.

The iconic road and America’s pastime

Chicago holds a special place in American history as the starting point of the legendary Route 66. With the road’s 100th anniversary approaching in 2026, there’s never been a better time to see where it all begins. A sign on Adams Street marks the official start of the ‘Mother Road’, a route that has shaped countless stories and communities on its journey west.

The city’s passion for sport is another key part of its identity. In 2027, this passion will take centre stage when the Chicago Cubs host the MLB All-Star Game at the historic Wrigley Field. One of the oldest ballparks in the country, Wrigley Field is an attraction in itself, known for its ivy-covered walls and electric atmosphere. Attending a game here is a quintessential Chicago experience, offering a glimpse into the heart and soul of the city.

To book your trip to Chicago, speak to your Travel Counsellor today.

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