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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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11 Nights – Jazz, Soul & Blues Self Drive Holiday

Departures September/October 2022

You will start off this fantastic Multi-Centre flying from either London or Manchester.

Taking in some of the most incredible scenery you could imagine, as well as some relaxing and charming hotels, this amazing holiday will take you from Chicago, Springfield, St Louis, Nashville, Memphis and New Orleans.

Your Itinerary Includes:

Stay 2 ni [...]

£1799

Based on 2 adults for 11 nights

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01772 337448

Chicago City Break 2022

Departures November 2022

Fly from Manchester or London where you will spend 4 nights at the Millennium Knicker Bocker Hotel.

This hotel is ideally located near Magnificent Mile in downtown Chicago – a famous stretch that’s home to over 400 retailers and high-end shops. Links to the public transport network, shops, restaurants, bars and pubs are situated within easy walking distance of the hotel, and you are [...]

£779

Based on 2 people for 4 Nights

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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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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 from London 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* Freehand Chicago Hotel.

[...]

£1489

Based on on 2 Adults for 10 Nights

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01772 337448

St Patrick’s Day in Chicago

Departures 16th March 2022

Depart from London Heathrow to Chicago direct with American Airlines!

Spend 4 nights at the Millennium Knicker Bocker Hotel. Located near Magnificent Mile in downtown Chicago – a famous stretch that’s home to over 400 retailers and high-end shops. You’ll be nestled into the retail haven of Magnificent Mile, proximity to some of the city’s most iconic landmarks like Cloud Gate and [...]

£689

Based on 2 People sharing for 4 nights

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01772 337448

Chicago & Toronto

Departures November 2022

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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01772 337448

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