Chicago Holidays - Holidays in Chicago, USA with American Sky

USA HOLIDAY DEALS

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Self-Drive Rhythms of the South 11 Days - Holidays to the USA & Canada with American Sky

Memphis, Price from £419

The cradle of American Music
Self-Drive Rhythms of the South 11 Days
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Groups of 10+

Car Rental

More Illinois Holidays

City Breaks & Luxury Hotels

Chicago Holidays

Chicago is a business center, with a diverse, powerhouse economy. It is also a tourism center, with world-renowned shopping, dining, museums, architecture, theater, music and more. Chicago’s architecture, unparalleled attractions, legendary sports and vibrant neighborhoods inspire and delight visitors. Whether explored by foot, motorcoach, trolley or boat, there’s only one city that tours like this

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Our Holidays in Chicago


Affinia Chicago

night from £59

Affinia Chicago, Executive guestroom

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


Best Western Inn

Price from £64

Best Western Inn, Exterior

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

Price from £69

The Sutton Place Hotel, Deluxe bedroom with great views of city

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

Price from £84

The Fairmont Chicago, Hotel exterior

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


Pre-Christmas shopping weekend in Chicago

3 nights from £635

Pre-Christmas shopping weekend in Chicago, Fairmont Hotel exterior - from river

With its stunning and diverse architecture, luxurious eating establishments and high-end shopping, Chicago has every cosmopolitan attribute. The spirit of the famed Blues and Jazz epoch is not lost in the modern city -- many venues and neighborhood clubs still make it their staple

Pre-Christmas shopping weekend in Chicago

Tours


The Great American Crossing

Price from £1,699

The Great American Crossing, New York - 5th Avenue

From 5th Avenue to Hollywood, this tour crosses North America calling at some of the most dramatic places in the USA. WDC; Detroit; Chicago with a cross-border visit to Niagara Falls and we are not even half way through! Getting nearer to the West Coast the landscape changes very dramatically and National Parks and Canyons are now the daily theme. The tour comes to a finish after stops in the Grand Canyon and Las Vegas before you see the star studded sidewalks of Los Angeles.

The Great American Crossing