Chicago Holidays

Chicago holidays offer a fantastic mix of attractions ranging from iconic skyscrapers with awe-inducing views to world-renowned museums and fabulous nightlife.

Cosmopolitan Chicago enjoys a picturesque setting on the shores of Lake Michigan and even has lakeside beaches. It also boasts a scenic river plus there’s plenty of green spaces including wonderful Millennium Park, home to the Cloud Gate sculpture.

A Chicago holiday has plenty to keep you busy. Explore the superb museums, indulge in shopping along Magnificent Mile, admire the famed architecture on a river cruise, have fun on the Ferris wheel at Navy Pier and ascend to the ‘360 Chicago’ observation deck for spellbinding views across the city. By night head to the Theatre District for dining and theatre shows, or tuck into a slice of deep-dish pizza before catching some live music in one of Chicago's many cool blues bars.

Trailfinders offers a range of Chicago holidays and our expert travel consultants are a mine of information about what to do here, often with first-hand travel experience. Whether you want a city break or hope to combine Chicago with an iconic road trip like Route 66 or a memorable rail holiday – they are the perfect people to ask.