Chicago Holidays

City urbanism meets tranquil parks and cultural hotspots in Chicago.

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

Time Zone

GMT -6 hours

Flight Time

Approx 8 hours; direct flights from the UK are available


USD - US Dollar

Visa Information

Endure you have a valid ESTA prior to travel



Health Information

No vaccinations required

You won't be lost for things to do in Chicago, with attractions and tours found across the city. The only question you'll need to ask yourself is what shall we do first.

  • 360 Chicago

    Offering the best view of across the city from 1000 feet above the magnificent mile, we love the TILT for it's jaw dropping experience of being tilted over the Chicago Skyline. This is an attraction you don't want to miss.

  • Mill Park Chicago

    Millennium Park

    A year round attraction, if your travelling in winter head to the park for some ice skating. If you're travelling during the summer months, find dozens of free events to attended from films in the park to outdoor concerts. With so much to be explored make sure you head to the park.

  • Magnificent Mile

    Hit the shops on the Magnificent Mile for an adventure in itself, Michigan Avenue not only has some great shopping but also has great restaurants, entertainment and plenty of history. Along the Magnificent Mile you will find three malls and many high end shops. If you are looking for bargain we recommended heading to Nordstorm Rack.

  • Navy Pier Chicago

    Navy Pier

    Navy Pier is the place to go for rides, entertainment, shopping, dining and nightlife. Children will love a ride on the Ferris Wheel and musical carousel before visiting the Children museum. For the adults from the Pier you'll be able to join a tour boat or a dining cruise ship.

  • Discover Chicago from the river

    Take a guided river boat cruise, this is the best way not only to see the amazing architecture of Chicago but to learn about the history of the city. For something a little more thrilling join a guided kayak tour and paddle your way through the heart of downtown on the famous Chicago River.

  • Route 66

    The start of Route 66

    Chicago is the place most people start the iconic Route 66 road trip. Almost 2,500 miles of stateside scenery, this journey should be on everyone's bucket list. There are many ways to take this journey from escorted tour in a coach to on the back of a Harley Davidson, to driving it yourself.

  • Isla, Destination Executive


    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."

  • Grace

    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
Magnificent Mile

Self Drive Chicago

Self Drive Chicago

Frequently Asked Questions

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