Chicago Holidays

City breaks to Chicago have plenty for you to get your mitts on. The scenery’s worth writing home about, and the street food will have you going back for seconds and thirds.

City breaks by one of the Great Lakes

Chicago cosies up to Lake Michigan’s southwestern shoreline, so the skyscraper views here are married up with waterfront ones. The city’s Lakefront Trail’s a smashing way to take it all in. Hire a bike and hit the lakeside paths – you’ll pass by dozens of beaches, pretty parks and Instagram-worthy backdrops. If you've got a head for heights, Chicago’s skyscrapers offer up next-level bird’s-eye views. The city’s home to bucketloads of rooftop bars and vantage points, like the 360 Chicago Observation Deck along the Magnificent Mile.

A thriving art scene

The street art in Chicago pulls in visitors from all over. In Millennium Park, the iconic Cloud Gate is the main event – this massive bean-shaped sculpture reflects its surroundings like liquid mercury. And over in Logan Square, the Greetings from Chicago mural’s hard to miss. If galleries are more up your street, you’ve got heaps to pick from. The Art Institute of Chicago’s a decent place to start – it gets bragging rights for housing the biggest collection of Monet’s work outside of Paris.

Food for thought

Deep dish pizza’s probably the first thing that springs to any food lover’s mind when they think of Chicago. But that’s just a drop in the ocean that makes up this city’s food scene. From Chicago-style hot dogs to Italian beef sandwiches, the city’s like a bumper buffer ready for you to dig your teeth into. And you don’t have to fork out loads of dollar to get your fix, either. Low-key food trucks dish up all the must-try snacks, like rainbow ice-cream cones and pizza by the slice.

All sorts of sports

America’s crazy about five sports – baseball, basketball, hockey, football and American football – and Chicago’s teams do pretty well in the job lot. So catching a game has a place on any self-respecting sports fan’s itinerary, whether it’s hoops, home runs or touchdowns on show. You could cheer on the Bulls in a basketball game at the United Center, or sing with the crowd at a Cubs game at Wrigley Field ballpark. But if you miss out on game tickets, don’t fret – you can nosey around behind-the-scenes on a stadium tour instead.

At a glance

Chow down on deep dish pizza
Bounce between buzzy Lake Michigan beaches
Admire iconic sculptures in Millennium Park

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.

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.

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.

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.