Compare Hotels in Chicago from NZ$139

Like your secret Big Brother addiction, America’s third-largest city flies surprisingly under the radar. With more than 40 museums, skyscrapers to rival New York’s and culinary delights that are even better than the Big Apple (well, according to locals, anyway), hotels in Chicago have all the glitz and glamour—without the paparazzi.

Things to Do in Chicago

Grant Park, near the Chicago Loop neighbourhood, has more attractions than the city has late-night bars. Check out “The Bean,” a reflective, bean-shaped sculpture, for some snaps that are sure to get your friends talking. You’ll have profile pics for years to come—try one in front of the modern Crown Fountain, which incorporates photos of Chicago residents on a giant video screen in the style of classic gargoyles—with water spouting from their mouths.

Did we mention late-night bars? Yep! Sometimes drinking ‘til 2:00 a.m. just isn’t enough, so more than 70 bars stay open until 4:00 a.m. in this party city. Whether you want fancy mixology, fabulous LGBT fun or a basement dive bar to contemplate where it all went wrong (or right!), you can take your pick thanks to Chi-town’s closing time commitment-phobia.

Getting To & Around Chicago

You’ll most likely fly into O’Hare International (ORD), but some flights are available to Midway (MDW). Both airports are connected to the city’s metro rail, the “L”; O’Hare via the Blue Line and Midway via the Orange Line. Chances are, the L will be able to drop you close to accommodation in Chicago. The Blue and Red lines run 24 hours a day, too, so you won’t even have to spring for a cab after you hit up those 4:00 a.m. bars.

Prefer to stick to your own schedule? You’ll be good to go with one of lastminute.com.au’s brilliant car hire options. Really want to blend in with the locals? Go on two wheels instead. Get a 24-hour pass from the nearest bike-sharing station, then make like a hipster and pedal to your nearest farmers market for seasonal produce and creamy artisan cheese—or buttermilk donuts from a food truck. After all, when in Chicago, do as the Chicagoans do: eat!

Best Time to Travel

No matter when you time your Chicago holidays, you’ll have tons of indoor and outdoor activities waiting for you. In the summer, catch the free Chicago Air and Water Show; Taste of Chicago, which includes world-renowned musical acts; or the Jazz Festival, which has brought the funk over Labor Day Weekend since 1979. In winter, the Magnificent Mile Lights Festival and the colourful Christkindlmarket will warm you up with holiday cheer—and the spiked eggnog doesn’t hurt. Plus, you can enjoy the Skating Ribbon, a ½-km pathway winding through Maggie Daley Park. Stop off for hot chocolate and selfies with the city skyline as your backdrop.

You don’t have to book any old Illinois hotel just because you forgot your holiday leave was coming up. lastminute.com.au has the best deals on accommodation and airfares. Search our Chicago hotels today and you’ll be seeing donuts and pizza in your dreams tonight.