Luxury Chicago Holidays

Chicago holidays offer the chance to explore a city that echoes with the sonance of jazz and blues; a city that boasts the perfect combination of culture and adventure. Dip your toes in the water of Lake Michigan at one of 26 free beaches, while Chicago’s impressive skyline towers behind you.

There’s a reason why Frank Sinatra couldn’t help but sing about this city. It buzzes with fascinating stories and its people with passion and the kind of generosity that the Midwest is famed for. With so much art, sports, shopping, music and waterfront activities, there’s something here to delight everyone. Chicago is particularly famous for its architecture and it’s plain to see why. The city is full of exquisite buildings, just as captivating to the untrained eye as they are to the most informed enthusiast. Take a tour of Chicago and appreciate its breathtaking skyline from ground level, visiting the likes of Millenium Park and Museum Campus along the way. For an even more breathtaking view, head to the Magnificent Mile and scale the iconic John Hancock Building up to the 360 Chicago Observation Deck and gaze out over the sprawling city and see the expanse of Lake Michigan.

Chicago: A City of Music

In a city so famed for its jazz and blues, the streets aren’t short of restaurants, breweries and bars that welcome you in with the sweet sound of a saxophone. Spend a relaxed night at Green Mill Cocktail Lounge, a friendly but sophisticated bar where musicians, so in love with the music, often play on until the early hours of the morning.

As the city sits at the start of Route 66, a Chicago holiday makes for a great starting points for multi centre holidays. Stop off in other iconic destinations, including St Louis, Las Vegas and the Grand Canyon National Park.