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Luxury Holidays North America / Chicago

The 'Windy City' offers an unforgettable Midwestern spirit and infectious energy.

'Home of the electric blues’, Chicago’s energy is infectious. From atmospheric jazz clubs and Broadway-style theatres, to Michelin-starred restaurants and designer shopping along the Magnificent Mile, the city is an enticing blend of American spirit and cosmopolitan charm.

Savour one of America’s finest city skylines on a river cruise, relax on Oak Street Beach by the shores of Lake Michigan or enjoy an injection of world-class culture with over forty museums, including the Art Institute of Chicago — the Midwest’s own Louvre.

Chicago Essentials

Approx. Flight Times London to Chicago 8 hours 25 mins
Time Difference GMT -6 hours in winter, GMT -5 hours in summer
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Chicago Hotels & Itineraries

Introducing some of the best 5 star resorts in Chicago.

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When to visit Chicago

The best times to visit Chicago are during the spring and autumn seasons, when temperatures are mostly warm and pleasant. With a host of festivals and events taking place, summer is the most popular time to visit Chicago; temperatures can be variable due to heat waves, humidity or strong breezes from Lake Michigan. Extreme cold temperatures can be expected from November to March, meaning visitors can benefit from excellent offers from hotels during this period.

Top 5 things to do in Chicago

  • Enjoy a VIP experience at one of Chicago's world-class comedy shows, with a pre-show reception and some of the best seats in the house
  • Explore the upscale boutiques of the Magnificent Mile with a dedicated personal shopper in tow, from Gucci and Chanel to Cartier and Bloomingdale's; in November, this designer shopping strip comes to life during the Magnificent Mile Lights Festival
  • Indulge in the smooth sounds of jazz with an exclusive backstage pass to the Chicago Jazz Festival, which entitles you to meet-and-greets and after party access
  • Take in the contrasting views by bike along the 18-mile eco-friendly Lakefront Trail, passing Lincoln Park, Navy Pier and Belmont Harbor
  • Experience the beauty of the city's architecture on a multitude of tours: admire the city skyline at 360 CHICAGO atop the John Hancock Center or explore iconic Mid-Century interiors designed by Frank Lloyd Wright

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We look beyond destination.
We curate exceptional experiences.

Our worldwide network, dedicated team of experts and wealth of knowledge is second to none, allowing us to open up your mind and take your breath away with awe-inspiring possibilities and new personal experiences that surprise, enlighten and transcend all expectations.

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Whether it’s glamour and guest lists you desire, an escape to a place where no-one is watching and anything is possible, or an adventure that no-one has dared take before - you will have access to the top suites, the most beautiful locations and a world of exclusive privileges.

We look beyond the usual.
We deliver dreams and desires.

We now live in an era of experience; it’s not just about where you can go, but who you can be and how you can feel. Carrier curate exceptional luxury travel experiences designed to fulfil your desires, dreams and goals, so bespoke you won’t find them anywhere else.

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