Chicago City Breaks 2025/2026
Also known as ‘The Windy City’, Chicago is the third largest city in the US and stretches along more than 26 miles of a beautiful lakefront. A Chicago city break will bring you everything from soaring skyscrapers to jazz culture and great street food.
Top Chicago Deals
Things to do in Chicago
Macy’s is the second largest department store in the world so surely that’s a must-see when in Chicago! You’re sure to find plenty of souvenirs for friends and family – and why not treat yourself to your favourite designer brands. Located on State Street, known as Chicago’s Main Street, there’s plenty of other high street shops to explore too.
If you’re more into breaking a sweat than shopping till you drop, a Chicago city break is still perfect for you. The Forge: Lemont Quarries is a 300-acre outdoor park with all the outdoor activities you could dream of. Climbing walls, mountain bike trails, zip lines and much more on offer. The Lakefront Trail is ideal for keen adventurers, with a 30km stretch perfect for cycling or running!
For art and culture lovers, The Art Institute of Chicago should be top of your list. Chicago’s best-loved museum hosts over hundreds of thousands of pieces from across the globe showcasing centuries of history. This includes famous pieces by Monet and Seurat, and even Grant Wood’s American Gothic.
The must-eats when in Chicago
A city break to Chicago is not complete without feasting on a traditional Chicago deep dish pizza! It’s packed full of tomato sauce and gooey mozzarella that melts in your mouth, held together with a crispy crust that makes the perfect base. We’ll be impressed if you finish one by yourself!
How about a Chicago style hot dog? A beef frankfurter in a poppy seed bun topped with mustard and green pickle relish, as well as onions, tomatoes, pickles and peppers. Strictly no ketchup allowed!
Keep your napkin ready with the Chicago Italian beef sandwiches. Starting with a crusty Italian roll, it’s filled with thinly sliced beef, cheese and peppers, and you can eat it dry or dip it in gravy! Now your Chicago city break is complete.
Non-stop entertainment
Chicago is home to top teams from the five major US sports, including baseball, American football, and basketball. Make your Chicago city break one to remember by experiencing the buzzing atmosphere firsthand of a live sports game. If that isn’t really your cup of tea, then how about a stadium tour instead to see where all the action happens?
A city full of speakeasy style bars, jazz music and cocktails – nightlife in Chicago will also never disappoint. Whether you’re looking for a chill evening or a lively night out the classic Chicago charm will tick all your boxes, sitting on a rooftop sipping prohibition themed cocktails or in a retro basement restaurant. I don’t know about you, but that seems pretty cool!
Similar USA city breaks
If you know the USA is where you want to adventure then there’s plenty of options as well as Chicago. Head to the famous Manhattan skyline with our great deals to New York, the home of the White House in Washington, or add some glitz and glam in the extravagant city of Las Vegas.