10 Essential Experiences in the Windy City

Changing flights at Midway or O’Hare? Treat yourself to a two-day layover, and use our list of things to do in Chicago as your guide to the best the Windy City has to offer.

Things to do in Chicago: Pizza City USA TourPhoto: Anna Waggy/Choose Chicago

Become a Pizza Snob

Chicago is synonymous with ooey, gooey deep-dish pizza—and that’s a bit of a problem for local ABC News food reporter Steve Dolinsky. “What you think of as Chicago-style pizza is not what people in Chicago actually eat,” Dolinsky says. In fact, deep-dish is one of 10 distinct styles of pizza on the Chicago food scene, several of which you’ll sample if you hop on the Pizza City USA tour. Guided by Dolinsky himself (at right, above), you’ll be shuttled to pizzerias across the city on a fascinating —not to mention gut-stretching—feeding frenzy. At Bonci in West Loop, you’ll tuck into Roman-style pizza (which closely resembles bruschetta), while at Lincoln Park’s Pizzeria Bebu, the menu is largely Artisan-style. Our pick for the best pie in the city? The true Chicago favourite—Tavern-style pizza, with its thin, cracker-like crust—at Pat’s Pizza (above). Family-owned since 1950, the impossibly charming old-school pizzeria is Chicago’s quintessential casual dining experience.

Chicago travel tip: Go hungry—and try to exercise restraint at the first few stops on the tour. In a pizza marathon such as this, pacing is everything.

Do you tend to let your taste buds guide your travel plans? Check out the world’s best destinations for foodies.

Things to do in Chicago: 606 TrailPhoto: Choose Chicago

Cruise the 606

What the Highline is to New York, the 606 is to Chicago. Built on an abandoned railway line, the three-mile elevated trail has proven an irresistible lure for runners, skateboarders and cyclists since it opened in 2015. For visitors to Chicago, it has the added bonus of serving as the perfect jumping-off point for exploring the four Chicago neighbourhoods through which it passes. To get the most out of the 606 on a tight turnaround, it’s best to rent a bike from a nearby Divvy stand (you’ll need a credit card), and pedal your way along the leafy, tree-lined path. Blessed with level paving, it’s a nice smooth ride with scenery that’s much more inspiring than your hotel gym. (Believe us—after that pizza tour, you’ll be needing a good sweat sesh.)

Chicago travel tip: Although Divvy single-trip rides are available for $3 a pop, the city’s extensive bike trails may tempt you to purchase a $15 day pass. Chicago’s expansive Lakefront Trail, for instance, stretches for 29 kilometres along the shore of Lake Michigan, connecting attractions like Navy Pier, Soldier Field and the Museum of Science and Industry.

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Things to do in Chicago: Shop the Magnificent MilePhoto: Magnificent Mile Association

Walk the Mile

It’s with good reason the stretch of Michigan Avenue north of Oak Street is known as “the Magnificent Mile.” Boasting some of the best shopping in the United States, it’s the ideal route to indulge in a bit of retail therapy. Here you’ll find the ultra-luxe flagship locations of Burberry, Zegna and Bloomingdale’s—attractions in their own right, and worth a gander even if you’re strictly window shopping. For a totally immersive taste of luxury living—without even opening your wallet—step inside the four-floor Ralph Lauren at 750 North Michigan Ave. Between its oak-panelled walls and blackened brass chandeliers, it’s more grand country house than high-end showroom, with only the occasional price tag to shatter the illusion.

Chicago travel tip: Although it’s easy to get distracted by the glitzy street-level shopfronts, don’t miss Water Tower Place—the Mile’s sprawling eight-storey mall.

Here are 10 more world-famous streets worth strolling.

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