Book flights to Chicago (ORD)

Things to do in Chicago

Step onto the Skydeck Chicago’s glass balcony and live the thrill of floating above the city. If you’re feeling a little adventurous, you can even step onto the all glass floor for a truly breathtaking, 360-degree panoramic view.

Millennium Park in downtown Chicago is a hub for bold architecture and public art. Marvel at the iconic Cloud Gate, lovingly dubbed as ‘The Bean’ by locals. This must-see landmark stands as a hallmark of Chicago’s artistic character, with its gleaming surface reflecting the city’s skyline. In summer, the park hosts concerts and events to enjoy too – all free of charge.

Visit the Chicago Cultural Centre to discover the Tiffany glass dome – the largest in the world of its kind. Architecture enthusiasts won’t want to miss Robie House, a UNESCO World Heritage Site designed by Frank Lloyd Wright, or the Tribune Tower, a testament to Chicago’s legacy as the birthplace of the skyscraper.

Activities in Chicago

You certainly won’t be short of activities to undertake in Chicago. Dive into its soulful roots by listening to a Chicago-style blues gig. The sound of guitars and husky vocals will transport you back to a whimsical era.

Delve into the city’s intriguing past at the Chicago History Museum. The museum features a number of exhibitions, including one dedicated to Abraham Lincoln’s life. The installation highlights Lincoln’s election in 1860, his leadership during the Civil War and his tragic assassination.  

For a more leisurely adventure, head to Navy Pier – a playground by the water where rides, restaurants, and theatres meet with stunning lake views. Up for some water fun? Take up a kayak tour down the Chicago River and paddle through the famed waterways, learning about the city’s architectural wonders from a unique perspective.

Food in Chicago

Naturally, you must sink your teeth into a deep-dish pizza when in Chicago – a masterpiece of gooey mozzarella, rich tomato sauce and a buttery crust that will leave you craving more. This hearty, cheesy concoction is a quintessential taste of Chicago’s extravagant food scene. Lincoln Park is the perfect neighbourhood to indulge in this local favourite, plus much more. 

For a glimpse into Chicago’s cultural roots and culinary creativity, order an Italian beef sandwich. This delectable mix of tender, spiced beef stuffed in a crusty roll, drenched in a savoury au jus and often adorned with peppers, is a true Chicago classic. 

Shopping in Chicago

For a shopping encounter like no other, make your way to the aptly named Magnificent Mile. High-end boutiques, luxury retailers, and well-known department stores line the streets with the finest fashion, jewellery and lifestyle items – all against the backdrop of Chicago’s spectacular skyline. 

Wander down State Street, a historic shopping destination that has long been the pulse of Chicago’s retail scene. From classic department stores to specialty shops, State Street offers a blend of nostalgia and modernity.

For a more intimate shopping trip, venture to Andersonville. Locally-owned boutiques display handcrafted jewellery and one-of-a-kind home décor pieces. It’s a place to indulge in the eclectic spirit of the city, where friendly shopkeepers are eager to share their curated collections.