
Route 66 Road Trip Holiday
Frequently Asked Questions
What’s the best place for a panoramic view over Chicago?
Willis Tower’s Skydeck Chicago offers a breath-taking view. It has a 1300 feet high, glass ledge extending four feet out from the building.
When is Chicago’s Blues festival?
For three days in early June the free to enter Chicago Blues Festival takes place. Here you can catch well known artists and rising stars of the jazz world.
Where can I see a traditional baseball game?
Chicago’s Wrigley Field is home to baseball, hockey, football and other sports – sometimes all at the same time. It’s also a concert venue. Look online to see what’s on while you’re here.
Visit Chicago’s America for its forward-looking attitude, beautiful modern architecture, clean open spaces and laid back Blues. When you’re finished in the city for the day, lie back on the lakeside beaches, or play in the refreshing water. Chicago is a great first step to your eclectic holiday.
Why you’ll love Chicago…
• Listening to live blues music in Chicago’s blues bars
• Strolling the atmospheric Chicago River Walk by night
• Cooling off with lakeside fun and relaxation
• Being overwhelmed by the stunning views over city and lake from Willis Tower’s Skydeck
• Taking in the contrasting vistas of city skylines
• Gliding along Chicago River, snaking through the modern architecture towering above you
• Riding the L train high above the streets of Chicago
• Watching and wondering at the rules of baseball in Wrigley’s Field
• Tasting your way around the city, starting with your favourite toppings on classic Chicago deep pan pizzas
• Playing with the magic of the Cloud Gate sculpture
• Trying something quirky with a doughnut tour of the city
• Cycling along the lakefront and taking in the lake’s vast waters
Did you know?
• Chicago is known as The Windy City because of the cooling winds coming off Lake Michigan.
• The Cloud Gate sculpture was built by a British artist, Sir Anish Kapoor. It’s built to give the appearance of liquid mercury.
• Chicago’s downtown area is known as The Loop.
Let's Chat
We have answers to all your questions.
Start planning your dream trip by talking to our Destination Specialists
Sign up for our newsletter
Receive the latest travel inspiration and destination news.

Three Easy Steps to a Tailor-made Holiday
The Hayes & Jarvis Way
Since 1952, our travel experts have been traversing the world to connect you with the very best our 60+ destinations have to offer. Tell us what your dream trip entails and we will craft it for you with precision and passion.