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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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*Featured Deal* Eastern USA Triple Centre

Departures January 2022

Fly direct From London for this epic USA three-city break.

New York City

First up, you’ll spend 3 nights in the big apple staying at the Row Hotel. This is located next to the wide awake Times Square.

Boston

Then onto Boston where you’ll check in to the Copley Square Hotel for 3 nights within the heart of the city. Here, you may want [...]

£979

Based on 2 people sharing for 9 nights.

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Chicago City Break 2022

Departures November 2022

Fly from your chosen UK airport in 2022 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 [...]

£639

Based on 2 people for 4 Nights

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01772 337448

2023 USA Triple-Centre

Departures January/February 2023

Book this amazing 2023 USA triple-centre today for just £939 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 [...]

£939

Based on 2 Adults for 9 Nights

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01772 337448

Chicago & Aruba

Departures Feb/March 2021

This Chicago & Aruba Holiday will see you spending 2 weeks away with 4 nights in Chicago and 10 nights in Aruba.

Start your holiday by flying from London Heathrow to Chicago. Spending 4 nights in a centrally located hotel. While in Chicago why not take the Inside Chicago and Pizza Tour. Taste the ‘real Chicago’ with a comprehensive tour of the city’s most popular, e [...]

£1999

Based on 2 people for 14 nights

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01772 337448

Chicago & New Orleans Twin Centre

Departures September - November 2022

Pillinger World Travel are pleased to offer this exciting Chicago & New Orleans 2022 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 [...]

£1499

Based on on 2 Adults for 10 Nights

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01772 337448

Chicago & Toronto

Departures November 2021

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 Faimont 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 se [...]

£885

Based on 2 Adults for 8 nights

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Southern Explorer by Rail

Departures February/March 2021

This 8 day Southern Explorer by Rail: Chicago to New Orleans. Visiting Chicago, Memphis & New Orleans including an Elvis experience excursion.

Day 1: Arrive Chicago On arrival into Chicago, take your included transfer to your downtown hotel. The rest of the day is at leisure to explore ‘The Windy City’.

Day 2: Chicago Enjoy a free day to explore. Take a shoreline cruise on [...]

£1099

Based on 2 people for 8 days

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01772 337448

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