Chicago Holidays

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.