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Chicago Holidays
Chicago is the USA’s third largest city, a powerful business centre that is also a great destination for a classic American holiday, with world-renowned shopping, dining, museums, architecture, theatre, music and more. Chicago’s architecture, unparalleled attractions, legendary sports and vibrant neighbourhoods and some fantastic hotels make for an inspiring city break or stop on a multi centre holiday.
American Sky offers many more quality hotels in Chicago – please call for details.
Our Holidays in Chicago
The Affinia Chicago features a prime location at the Windy City’s epicenter of entertainment, culture, shopping and business including the Hancock Observatory, Art Institute of Chicago, the Magnificent Mile, and Navy Pier
Affinia Chicago
Philadelphia, famous as the birthplace of life, liberty and the pursuit of happiness, the city offers much more than cobblestone streets and historical landmarks. Cultural, culinary, artistic and ethnic treasures abound in this city and its surrounding countryside.
Chicago is everyone’s kind of town, with attractions and activities galore. See all the famous sights, then go to a show in the theatre district or a Cubs game at historic Wrigley Field, followed by a late-night visit to a blues club or jazz bar.
Philadelphia & Chicago Twin Centre
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With attractions and activities galore, Chicago is everyone’s kind of town. See all the famous sights, then go to a show in the theatre district or a Cubs game at historic Wrigley Field, followed by a late-night visit to a blues club or jazz bar. From major department stores to chic designer boutiques, Chicago’s boulevards and tree-lined streets are a haven for serious shoppers.
Chicago Pre Christmas Shopping
Best Western Inn
1 night from €99
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Location just half a block east of Chicago’s Magnificent Mile close to nightlife, art museums, galleries and fine shopping this friendly hotel provides a great base to explore the city
Best Western Inn
The Sutton Place Hotel
1 night from €107
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Rising above Chicago’s exciting Gold Coast, The Sutton Place Hotel Chicago, a AAA-4 diamond facility, offers a unique mix of style and serenity in the middle of the bustling Chicago lifestyle
The Sutton Place Hotel
The Fairmont Chicago
1 night from €130
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Conveniently located in the heart of downtown Chicago, near major cultural attractions, Navy Pier, the city’s business and financial district and the world renowned shopping along the Magnificent Mile
The Fairmont Chicago
Tours
Self-Drive American Music & Movie Trails
Price from €1,399
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For film and music enthusiasts, this tour gives you the opportunity to visit first-hand some of the most familiar of U.S. sites that have been extensively used in hit movies. Cities like Chicago, Memphis, Birmingham, and New Orleans all have their place in representing the history of film and music.
Self-Drive American Music & Movie Trails
Self Drive Route 66
Price from €1,419
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Route 66 Self Drive AT.
Daily Departures. Prices shown include transatlantic scheduled flights, 15 nights accommodation and car rental (economy size) and are per person based on 2 adults sharing. Supplements may apply within certain date bands. Different hotels of similar standards maybe used on certain departures. Parking fees are not included.
Self Drive Route 66
Self-Drive The Great Lakes
Price from €1,519
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From the Windy City venture to the Twin Cities, to Longfellow’s inspiration point, to the thundering Niagara and to the Rock’n’Roll Hall of Fame.
Self-Drive The Great Lakes
The Great American Crossing
Price from €2,119
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From New York City to Los Angeles, this classic American tour crosses the continent, stopping off at some of the most dramatic and exciting places en route - from Niagara Falls to Chicago and the Grand Canyon to Las Vegas. See it all on this epic journey.
The Great American Crossing
Route 66
Price from €2,709
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Journey across the USA from east to west with everything taken care of for you. Chicago - the windy city, Branson and Oklahoma City, Amarillo and Albuquerque, Winslow, Grand Canyon, Vegas and finishing in Los Angeles - the city of angels!
This is a first class tour, with transatlantic schedule flights, transfers, superior hotels, deluxe motorcoach transportation and the services of an expert Tour Director all included in the price.
Route 66
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