Chicago holidays

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.