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Holidays in Chicago

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Special offers available in Chicago!

One of the reasons you should book with Virgin Holidays is all of the extras you get. See the Special offers tab to find out what great deals are available in Chicago.

Chicago deals from £709!

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Check out our range of excursions

Make sure you have a holiday to remember! Choose from one of our fabulous excursions!

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Destination information

Music buffs will love its vibrant music scene with world-class acts taking to the stage nearly every week in venues such as the House of Blues, the Cotton Club and Hot House. Theatre-goers are also spoilt for choice with a scene to rival that of New York! Cultural attractions include the Art Institute of Chicago and the Sears Tower Skydeck, the 2nd tallest structure in the world. The Loop, Chicago's central business district, is where the world's first skyscraper was built and is a living museum of modern and 19th-century architecture. For upscale shopping, head to the Magnificent Mile for stores such as Bloomingdale's, Lord & Taylor, Tiffany's and Nordstrom.

Eats & drinks

Head to Chinatown, Greektown or Little Italy for international cuisine, find some superb dining and fun bars around Michigan Avenue.

Events calendar

Key Events


Jan 2013– Winter Flower and Train show
Feb 2013– Auto Show
March 2013 -Academy Awards Party
April 2013 - Chicago Improv Festival
May 2013 - Art Chicago
June 2013 - Chicago Blues Festival and Chicago Gospel Festival
July 2013 - Chicago Summerdance
August 2013 - Air and Water Show
September 2013 - Chicago Jazz Festival
October 2013 - International Film Festival
December 2013 - Christkindlmarket
Please note: all events listed are for helpful information only and many are subject to entrance fees and/or prior reservation, and may be cancelled at any time. Please check with the relevant tourist office if you need further information on these or any of the other events in this region.


Our Top 5 hotels

Essex Inn

This hotel offers stylish accommodation and excellent facilities in a central location. Take the hotel's free shuttle to the 'Magnificent Mile' for a day of shopping, then relax by the rooftop pool admiring the spectacular views over Grant Park and Lake Michigan!

The James

Unique style and exceptional service characterise The James, the first in a new line of establishments that fill the gap between boutique and luxury hotels. Modern comfort and old-fashioned hospitality are sure to delight, as are the fantastic range of mod cons that all rooms feature.

Hilton Palmer House

This famous Chicago hotel combines modern comfort with over 135 years of elegance and service. There are plenty of amenities on site to tempt you, including Lockwood Restaurant, Potters Lounge and the lobby bar, an indoor heated swimming pool and full fitness centre.

Radisson Blu Aqua Hotel Chicago

Radisson Blu hotels are recognised throughout the world for thought-provoking contemporary style, and this one found in the new landmark on the Chicago skyline the Aqua Tower, does just that. One of the funkiest up-to-date hotels around; location, rooms, facilities and genuinely welcoming staff hit the bullseye on all 4 counts, and then some.

Fairmont Chicago Millennium Park

Rising gracefully above Grant and Millennium Parks, the Fairmont exudes first class elegance and the grand circular lobby sets the Fairmont's tone straight away: upscale and lavish. Centered in the lobby is the Eno Wine Room, a favourite of both locals and guests. Grab a glass of wine and pair with savoury cheese or a sweet chocolate truffle.


Different destinations have different magic touches so make sure to check them out to see what makes your holiday with us so special.

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Getting there

Flights with Virgin Atlantic (seasonal) or American Airlines.

Return airport transfers are available at the following price: £52 per person.


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