Chicago Holidays

The Windy City

City urbanism meets tranquil parks and cultural hotspots in Chicago, the Windy City.

For panoramic views of the city, head to the Willis Tower; the 103rd floor Skydeck to be exact. Gaze down on the glittering skyline and across Lake Michigan for a sight punctured with skyscrapers and natural beauty. If it’s awe-inspiring architecture you’re after, head to Millennium Park, home to the world’s largest rooftop garden, before settling into one of the city’s many Blues Bars for some 1920’s music and a drink or two. The Field Museum is well worth a visit too, housing artefacts from the prehistoric age, ancient Egypt and China’s Terracotta Warriors.

For more city buzz, head to New York before or after your Chicago break. Or, visit Los Angeles for some Hollywood glamour and designer shopping. 

Destination Highlights
  • Explore Millennium Park
  • Hit the shops on the Magnificent Mile
  • Take a boat tour for a different perspective of the city
  • Dine on Chicago's famous deep dish pizza
  • Start your epic adventure for Route 66
  • See the spectacular views from 360 Chicago
Essential Information
  • Time Zone GMT -6 hours
  • Currency USD - US Dollar
  • Visa Information Endure you have a valid ESTA prior to travel
  • Language English
  • Flight Time Direct flights are available with Aer Lingus, United Airlines or American Airlines.
  • Health Information No vaccinations required

Top Tips from our Experts


Destination Executive

"I recommend hiring a bike for a fun and different way to see the city, its such an easy way of seeing the sights. Also don't forget to try the famous Chicago deep dish pizza, it was the best pizza I have ever tried."


Commercial Executive

"I was brave enough to try the Chicago 360 Tilt, will you be? "

Types of Chicago holidays

Chicago Skyline

Chicago Multi Centre Holidays

Multi Centre Holidays
Eaglerider road trip along Route 66

Chicago Tours

Magnificent Mile

Self Drive Chicago

Self Drive Chicago

Frequently Asked Questions

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