Loading your search results...


Close Menu

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 City Break 2019

Departures February - March 2019

Fly from your chosen UK airport in 2019 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 [...]


Based on 2 people for 4 Nights

More on this offer

Discuss this offer with a member of our team
01772 337448

Chicago, Memphis & New Orleans Multi-Centre

Departures Between 03rd September - 29th October 2018

Get away to 3 iconic American destinations with this multi-centre break to Chicago, Memphis & New Orleans.

The price includes flights from various UK Airports, followed by 3 nights at the 4* Westin Michigan Avenue hotel in Chicago.

You’ll then take an overnight Amtrak train to Memphis stay for 2 nights at the 4* The Guest House at Graceland hotel in Memphis.

Fina [...]


Based on 2 Adults sharing for 10 nights

More on this offer

Discuss this offer with a member of our team
01772 337448

Chicago & New Orleans Twin Centre

Departures September - November 2018

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 holiday [...]


Based on on 2 Adults for 10 Nights

More on this offer

Discuss this offer with a member of our team
01772 337448

Jazz, Soul & Blues Self Drive Holiday 2020

Departures May - June 2020

Fly from Various UK airports for this quirky Jazz, Soul & Blues Self Drive Holiday 2020. Staying 2 nights in Chicago, famous for it’s legendary blues and jazz, the electric music can be heard nightly in the lively Chicago music venues throughout the city. Chicago is an all-encompassing music playground, piping out sounds 7 days a week, whether your taste is  classical music, hip hop, [...]


Based on 2 people for 11 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.