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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 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 [...]

£699

Based on 2 people for 4 Nights

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01772 337448

Chicago & Las Vegas

Departures September/October 2023

This twin center Chicago and Las Vegas Holiday will see you spend 9 nights exploring the best of these two cities, from sightseeing to nightlife.

Start this amazing adventure by flying from the UK to Chicago were you will spend 3 nights in a centrally located hotel. Whilst in Chicago why not take a visit to the 360 Chicago which has one of the best views of Chicago and also features a TI [...]

£1089

Based on 2 people 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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Discuss this offer with a member of our team
01772 337448

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