Chicago holidays

Buckingham Fountain, Grant Park, Chicago

Popular holidays

When it comes to USA city breaks, Chicago holidays are among the best. This lakeside city lines up Lake Michigan beaches, iconic skyscrapers, world-renowned art, a vibrant music scene and retail paradise on the Magnificent Mile.

What to expect in Chicago

Plotted on the south-western shore of Lake Michigan, Chicago – nicknamed the Windy City – pairs waterfront views with skyscraper-clad skylines. You can take it all in with a walk or a bike ride along the 18-mile Lakefront Trail, which is dotted with pretty parks and areas of open water, including Montrose Beach. A stroll around the restaurant-and-ride-packed Navy Pier is a must, too. From there, you can hop on a boat and head out on a Chicago River cruise to tick off even more sights without tiring yourself out.

Exploring art in Chicago

Chicago’s a haven for art enthusiasts. There’s the Art Institute of Chicago, for starters, which houses paintings by Monet and the Thorne Miniature Rooms. Then you’ve got the Corbett vs Dempsey gallery, whose collections include contemporary paintings and prints. And outside, the most famous landmarks in Chicago’s art scene include Cloud Gate – a sculpture in Millenium Park famously nicknamed The Bean – street murals like the iconic Greetings from Chicago in Logan Square, and Buckingham Fountain.

Chicago’s famous foods

It’d be rude to come to Chicago and not try some of its iconic deep-dish pizza. Chicago-style hot dogs and Italian beef sandwiches are also among the city’s famous foodie staples, and you won’t need to look far to find them as local street food trucks are parked up all over the place. If you fancy something more upmarket, head to America’s meatpacking capital where you’ll find classic steakhouses by the dozen. And for more diverse dining options, there are neighbourhoods like River North and the South Loop.

Major sports in Chicago

Chicago’s home to more than its fair share of major American sports teams, so it’s no surprise that taking a stadium tour – or better still, seeing a game – are among the top things to do here. Watch the Cubs play baseball at Wrigley Field, where there’s still a hand-operated scoreboard and century-old stands. Or, cheer on the Bulls in basketball at the United Center, where you’re virtually guaranteed a buzzing live game atmosphere. And if you’re into ice hockey, you can watch the Chicago Blackhawks take to the rink.

Popular hotels in Chicago

Top things to see and do in Chicago

Beaches

Chicago’s hidden beach scene

Beaches might not be the first thing that come to mind when you think about Chicago, but there’s plenty of them here to shout about. The city packs in an impressive 15 miles of sand along its 26-mile patch of the Lake Michigan shoreline, so you might have a hard time deciding which part to visit first.

The big beach

Oak Street Beach is probably Chicago’s most popular lakeside haunt. That’s partly thanks to its central spot in the busiest part of the city, but people flock here for the clear, shallow water and clean sand, too. On top of that, it boasts a picture-worthy city skyline as its backdrop.

The secret beach

If you prefer to avoid the crowds, make a beeline for 12th Street Beach – it’s tucked away behind the Adler Planetarium, next to Chicago’s Museum Campus. This small strip of sand lies right next to a big park, so it makes a great spot for a peaceful lakeside walk.

Shopping

Bargain buys

Maxwell Street Market first appeared on the Chicago map in the 1800s, and today it’s a hotspot for thrifty shoppers looking to grab a bargain. Take a walk through the market stalls and you’ll spot handmade crafts, second-hand clothes and homewares.

Mid-range buys

If you fancy a little retail therapy, Chicago’s Magnificent Mile is a great place to start. You’ll find around 450 shops here, from massive department stores to quirky boutiques. The mile-long strip’s also home to a handful of rooftop bars, where you can stop for a drink and admire views of the city skyline.

Designer buys

Oak Street, in Chicago’s Gold Coast neighbourhood, is the go-to destination for high-end designer stores. Here, a stack of luxury brands like Prada, Hermes and Chanel share the tree-lined avenue with historic stone-built mansions.

Nightlife

Laid-back evenings

One of the best ways to round off a busy day of sightseeing is to cosy up with a cocktail and watch the sunset at one of Chicago’s rooftop bars. Depending on which one you choose, you’ll get sweeping views of the city’s iconic skyline or Lake Michigan. And most are open year-round.

Lively evenings

The city’s packed with speakeasy-style bars and nightclubs, and they’re just the thing if you’re looking for a taste of the classic Chicago. Many are tucked away in restaurant basements or behind nondescript doors, and inside, you’ll find retro decor and menus full of prohibition-themed cocktails.

Food & drink

Deep dish pizza

No trip to this city would be complete without trying a slice of the famously delicious deep dish pizza. This Chicago staple is made up of a crispy crust topped with a generous helping of gooey, stringy mozzarella cheese, your favourite toppings, and finally, lashings of zesty tomato sauce.

Original Rainbow Cones

The Original Rainbow Cone has become a bit of a Chicago classic. The ice-cream recipe’s been virtually unchanged since 1926. It’s made up of five flavours – chocolate, strawberry, orange sherbet, pistachio and Palmer House – a mix of vanilla, cherry and walnut. You’ll find it in stores and ice-cream trucks all over the city.

Chicago-style hot dogs

There’s a strict no-ketchup rule when it comes to the classic Chicago-style hot dog. This must-try snack starts with a beef frankfurter on a poppy seed bun. Then, it’s topped with yellow mustard, green pickle relish, chopped onions, tomato wedges, a pickle spear, spicy sport peppers, and a sprinkling of celery salt – in that order.

Italian beef sandwiches

These messy sandwiches are made up of thinly sliced peppered beef, sweet or hot peppers and gravy, all piled into a crusty Italian roll. If you’re a die-hard gravy fan, you can order it ‘dipped’ – meaning the whole sandwich will take a bath in the beef stock, or au jus as it’s often called. Just remember to have a napkin at the ready.

Jibarito

The Puerto Rican-inspired jibarito is a sandwich made with thinly sliced steak, garlic mayonnaise, tomatoes, lettuce, onions and cheese. There’s no bread to be seen here, though – the filling is wedged between two crispy slices of fried plantain. It was first served in the 90s, and it’s since earned its status as a must-try Chicago food.