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Luxury Chicago & Mid West Holidays

Journey to a city that blends modern skyscrapers with historic buildings and vibrant parks with lakeside beaches.

Guide to Luxury Holidays in Chicago & Mid West

Nicknamed the Windy City, Chicago is a diverse place with many attractions. At the centre of the city, known as Loop, iconic architecture lines broad streets and Art Deco buildings sit beneath massive skyscrapers. The area is home to several impressive museums, like the Museum of Contemporary Photography or Federal Reserve Bank of Chicago Money Museum, and a charming downtown theatre district that hosts off-Broadway musicals. Head north to the Magnificent Mile, here you’ll discover an exclusive strip of world-class gourmet restaurants, luxury boutiques and vertical shopping malls such as 900 North Michigan Shops, Water Tower Place and The Shops at North Bridge. Explore renowned landmarks like The Wrigley Building, historic Chicago Water Tower and sleek, Gothic-inspired Tribune Tower. Take a moment and admire the stunning vistas of this lively district, one of the world's premier commercial avenues. Head across the bridge to New East Side to experience a different side of Chicago. In this neighbourhood, you'll find urban nature retreats in the form of the vast Millennium Park or Lakeshore East Park. The Chicago River also winds through New East Side offering you the chance to go boating and kayaking. It's also situated on the banks of Lake Michigan and boasts plenty of soft golden lakeside beaches with impressive views of Chicago’s futuristic skyline.

Chicago enjoys warm summers and cold winters. In winter, temperatures drop to around three degrees Celsius and snowfall transforms the city into a magical winter wonderland. The brilliant Christkindlmarket, Chicago’s Christmas market, also comes to town. Summer brings warm weather and sunshine with temperatures soaring above 25 degrees Celsius – perfect weather for the beach. Early autumn sees highs of 20 degrees Celsius with temperatures getting colder as winter approaches. Whatever the weather, Chicago is a year-round destination thanks to its wealth of attractions and museums.
As with any holiday, it's a good idea to carry some identification with you at all times. British citizens need a Visa Waiver Programme or a visa to enter the USA. Visit GOV.UK for more advice on passports, visas and travel.
Start your day with a full American buffet breakfast and look forward to award-winning dinner menus at luxury hotel restaurants. Enjoy seared steaks and fresh seafood dishes such as pan-roasted Alaskan halibut or lobster nachos. Try international menus serving authentic Chinese, Italian and Mediterranean cuisine. Dine with panoramic views of Chicago’s skyline, Lake Michigan, Chicago River or Wrigley Clock Tower. Relax on a rooftop lounge with live music and a glass of champagne. Sample international wines, local craft beers and signature cocktails.
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Chicago & Mid West holiday types