We use cookies on our website in order to improve your experience. By using our website you consent to our use of cookies.

We have been voted
Online Travel Agency Of The Year
by the two largest travel industry publications.
This has been 5 times in the last 20 years.
To see our 25+ travel awards, visit
https://www.holidaysplease.co.uk/awards/

Chicago Holidays

Time Difference -05:00 GMT
Average Temperature 25°C
UK Flight Time 8 Hours
Fly To Chicago O'hare International

Chicago Holidays

Known as the 'windy city,' Chicago is the major metropolis of America's heartland. The city is home to 3 million people so there's always a lot to see and do, making it a great holiday destination.

It is also home to some world famous hotels such as the Langham, Chicago.

Lose yourself in the hustle and bustle as you witness giant skyscrapers which look as though they have risen right out of Lake Michigan. The city has built its reputation on international business making it a commercial capital with a combination of breath-taking architecture, as well as outstanding theatre, arts and sports.

Make sure you climb the Sears Tower, one of the tallest in the world, and witness the breath-taking sights beneath you. Shop until you drop at the array of shopping malls and enjoy cuisines from all over the world in this ethnically diverse city.

Fill that hungry appetite with a famous Chicago-style-deep pan pizza or a jumbo Chicago-style hot dog, the choices are endless. For the sports fans, be sure to visit the home of world-class sports teams including the Chicago Bulls and the Chicago White Sox. Don't forget to catch the distinctive sound of the famous Chicago-style blues music at a live music lounge.

Be sure to take a day trip to Oak Park where you can witness Ernest Hemingway's birthplace home and explore the Nobel Prize-winning author's life at the nearby museum. Chicago offers you endless attractions, cuisines and sights so why not grab a piece of the action and choose Chicago for your next holiday, simply put in an enquiry now and one of our sales team will be in touch.

Things to do

  • Navy Pier
  • Museums
  • Art galleries
  • Skydeck Chicago
  • Magnificent Mile

Chicago Holidays

Good News! There are 5 suppliers who can supply prices.

We can get prices from tour operators without giving them your details. and will provide expert, impartial advice quickly. Just enter your details below...

100% Privacy Guaranteed

We respond in minutes and hours rather than days and weeks.

Benefits of using Holidaysplease
  • Get options without giving your details to lots of companies
  • Impartial, truly expert advice
  • Trust Pilot Top 3 for Customer Service
  • UK Online Travel Agency Of the Year 2023/24
  • 100% Privacy Guaranteed