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About Chicago

Located on the banks of the vast Lake Michigan in Illinois, the sophisticated city of Chicago is one of the largest and most vibrant cities in the entire U.S., famous for soaring skyscrapers and a wonderful heritage of sports, industry, and effervescence.

Known as the ‘Windy City’ and home to the skyscraper, the city is instantaneously identifiable for its high-end culinary delights, stunning architecture, wonderful green parks, and numerous shopping opportunities; it is a truly spectacular city to visit.

Freezing in the winter and hot in the summer, the ‘Windy City’ doesn’t do things by halves. We recommend visiting either during the Spring or the Autumn months. The temperatures are cooler than the summer months however, they are still mostly warm and dry (in the mid 20 degrees celsius) and perfect for exploration. This is also when the city comes to life with festivals and the tourist crowds are more manageable.

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Chicago City Break 2020

Departures November 2020

Fly from your chosen UK airport in 2020 for this Chicago city break, staying 4 nights at the iconic 4* Warwick Allerton hotel.

The hotel is ideally located on Michigan Avenue, right at the heart of the historical Magnificent Mile. The John Hancock Tower is just 3 blocks away from this hotel. Links to the public transport network, shops, restaurants, bars and pubs are situated within easy [...]

£579

Based on 2 people for 4 Nights

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01772 337448

2021 USA Triple-Centre

Departures January/February 2021

Book this amazing 2021 USA triple-centre today for just £849 pp, and visit three iconic cities in one trip! Once you land in the USA, you’ll stay for 3 nights in Chicago, the Windy City, at The Inn of Chicago, a boutique hotel, situated in the heart of downtown Chicago, and just a short walk from the Magnificent Mile and other attractions. Chica [...]

£849

Based on 2 Adults for 9 Nights

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Chicago & New Orleans Twin Centre

Departures September - November 2020

Pillinger World Travel are pleased to offer this exciting Chicago & New Orleans Twin Centre holiday.

Start your adventure by flying to Chicago where you will find a city full of culture, fine dining and beautiful scenery, explore this cosmopolitan city and relax by one of the beautiful lake-side parks, here you will spend 5 nights at the 4* Raffaello hotel.

Then continue your [...]

£1399

Based on on 2 Adults for 10 Nights

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01772 337448

Chicago & Toronto

Departures November 2020

This Chicago & Toronto holiday will see you visit Chicago for 3 nights, Toronto for 3 nights finishing with 2 nights at Niagara Falls.

Flying from regional UK airports you will fly to Chicago for 3 nights at the Freehand Hotel. Chicago is a city of variety, from parks and beaches to live jazz and blues clubs. You will be sure to spend the 3 nights exploring all that is available to s [...]

£875

Based on 2 Adults for 8 nights

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01772 337448

Cincinnati City Break

Departures April/May 2020

Fly to Cincinnati and spend 5 nights at the wonderful Hampton Inn Cincinnati Riverfront Hotel Downtown.

This is a fabulous city in Ohio, situated right on the Ohio River. The Over-the-Rhine district is best known for its 19th-century architecture which includes Findlay Market, this has famous food and craft vendors. In addition to the north of the [...]

£699

Based on 2 Adults for 5 nights

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01772 337448

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