Chicago holidays

Buckingham Fountain, Grant Park, Chicago

Popular holidays

City breaks to Chicago have plenty of strings to their bow, from waterfront parks to art galleries in the shadow of skyscrapers.

The Windy City

Chicago’s a city of many nicknames, but one of the main ones is ‘the Windy City’. But contrary to popular belief, it’s not because of the general weather – a tornado once blew through in the 1800s, and the moniker stuck. Instead, lots of locals prefer the ‘City by the Lake’ title, thanks to Chicago’s scenic spot next to Lake Michigan. Pretty parks make way for skyscrapers as you get towards the centre, so you’ve got the best of urban life and natural greenery.

Cultural spot

Culture means something different to everyone, but Chicago has a few different versions to keep the masses happy. Art is the first one – there are striking public displays like the Cloud Gate sculpture in Millennium Park, plus historic works of art by the likes of Monet in the Art Institute of Chicago. At the other end of the scale, foodie culture is on display on every major street corner. Food trucks are a big deal in Chicago, and they don’t scrimp on quality. Pizzas come in every shape and size – from deep-dish to thin-and-crispy – and messy Italian beef sandwiches are a must-try.

Stadium selection

Ask anyone in America, and they’ll tell you that Chicago knows a thing or two about sports. From the Chicago Bulls in the NBA to the Chicago Bears in the NFL, there are top franchises in all of the major leagues. For one of the best stadium tours around, head to Wrigley Field – the famous home of the Chicago Cubs baseball team.

Popular hotels in Chicago

Top things to see and do in Chicago

Shopping

Bargain buys

For one of the cornerstones of Chicago’s market scene, head to Maxwell Street Market. Handcrafted souvenirs, vintage clothes and other bits and bobs are sold here, and the market itself has been around since the 1800s.

Mid-range buys

Hit up the Magnificent Mile to sample the best in high street retail therapy. There are more than 400 stores clamouring for attention, including sprawling department stores and dainty independent places.

Designer buys

Thee Gold Coast neighbourhood isn’t just prestigious by name – the shopping scene here is really fancy, too. High-end brands like Prada and Chanel have stores here, so you won’t be short of luxury shopping options.

Nightlife

Laid-back evenings

Because Chicago’s skyline is a dot-to-dot of modern skyscrapers, bar owners soon cottoned on and started setting up rooftop bars where you can soak up the views. Pick one in the city centre, and you’ll have excellent views of the cityscape from up high.

Lively evenings

You can feel like a VIP by seeking out one of Chicago’s speakeasy bars – these are places that are hidden in plain sight, and sometimes even require a password to get in. They’re usually decked out in retro themes, and serve some of the best cocktails around.

Food & drink

Deep dish pizza

This sort of pizza is a Chicago calling card – the slices are much thicker and doughier, with heaps of tomato sauce hiding away beneath the mozzarella and toppings. The crust, as obvious as it may sound, is especially crisp on these pizzas, too.

Original Rainbow Cones

As far as colourful ice-creams go, this local speciality takes every colour from the palette. A flavour called Palmer House – made of vanilla, cherry and walnut – is the base, and there are scoops of chocolate, strawberry, orange and pistachio to go with it.

Chicago-style hot dogs

Everything’s a bit different when it comes to hot dogs in Chicago. Instead of pork sausages, a beef frank makes up the main part of the snack. It’s placed in a poppy seed bun with yellow mustard, relish, chopped onions, tomato chunks, spicy peppers and shards of pickle.

Italian beef sandwich

Wafer-thin slices of tender peppered beef are piled up in this sandwich, with sweet peppers and gravy ladled on, as well. That’s the tame version – you can have your sandwich dipped in beef stock to make it super juicy, just make sure you’ve got a serviette ready.

Jibarito

Chicago chefs channel Puerto Rican flavours in this dish, which takes thin slices of steak and tops them with tangy garlic mayo, lettuce, tomatoes, onions and cheese. And you can forget about what sort of bread it’s served in – two fried slabs of plantain are subbed in to contain the fillings.