Loading your search results...


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.

  • Offers
  • Gallery

Chicago 7 Night Break

Departures March 2023

Chicago is a city of variety, from parks and beaches to live jazz and blues clubs! Fly direct from London Heathrow and spend 7 nights at the Millennium Knickerbocker Hotel. Includes breakfast!

Whilst in Chicago take a River Tour along Magnificent Mile or visit Lincoln Park Zoo. Take a day trip out to the Navy Pier, a 3,300 foot-long Pier located on the shoreline of lake Michigan. The Nav [...]


Based on 2 adults for 7 nights

More on this offer

Discuss this offer with a member of our team
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 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.



Based on on 2 Adults for 10 Nights

More on this offer

Discuss this offer with a member of our team
01772 337448

The Ultimate Multi-Centre!

Departures March - April 2023

This is the ULTIMATE USA Multi-Centre…


New York 4 nights

Washington 3 nights

Chicago 3 nights

Start off this fantastic offer in the heart of NYC at The Row. Set in New York City’s vibrant Theatre District, Row NYC offers proximity to Times Square and all its exciting hustle and bustle. Next spend 3 nights at the YOTEL in Wa [...]


Based on 2 people for 10 nights

More on this offer

Discuss this offer with a member of our team
01772 337448

Join our newsletter

Sign up for our latest offers, news, and tips.