North America & Canada


The Windy City

The Windy City is one of our most popular holiday destinations, so if you’re dreaming of a trip to Chicago, then Questor Travel is here to ensure you get the very best experience. As famed for its gangsters as it is for its architecture, there’s no shortage of things to do in Chicago if you make this your next holiday destination.

See the City from Every Angle

Those with a head for heights will immediately want to head for the 360 Chicago Observation Deck, with panoramic views over the sprawling metropolis. Perched 94 floors above the streets of the Windy City, the TILT experience is certainly one for thrill-seekers. When the evening draws in, you can watch the city light up from the restaurant at the top of the Willis Tower Skydeck, where Chicago’s famous deep-pan pizza is a must.

Explore on Foot

At street level, Chicago is a city with a real buzz to it and exploring on foot lets you take in the countless incredible local attractions. A stroll along the riverfront allows you to fully appreciate the imposing architecture of the city, with towering skyscrapers alongside more historic gems. Walk the Magnificent Mile at the heart of the city to really soak up the atmosphere, and enjoy the endless shopping and dining opportunities.

Feel the true city spirit

Whether you choose to explore on foot or take a cruise, Chicago has a very different feel to many American cities. There’s a unique sense of history to the older parts of town, where the infamous mob ruled for many years and became an important part of the city’s past.


There’s never a dull moment!

However long or short your trip to the Windy City, you’ll have plenty of things to do and never a dull moment. The city teems with fantastic galleries and museums, including the Field Museum and the impressive Art Institute of Chicago. Wherever your interests lie, Chicago will never disappoint.

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