48 Hours in Chicago: The Best Things to Do in Chicago on a Two-Day Layover

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.

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Things to do in Chicago: Pizza City USA Tour
Photo: 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.

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Things to do in Chicago: 606 Trail
Photo: 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.

Don’t miss these summer vacations everyone should take before they’re 50.

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Things to do in Chicago: Shop the Magnificent Mile
Photo: 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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Things to do in Chicago: Flight Club Darts
Photo: XVThree

Master the Art of Darts

Remember how much fun you had playing five-pin bowling as a kid? Swap out the lanes for dartboards, add an award-winning bar, surround it with industrial-chic décor, and you’ve got Social Darts. Whether you’re in Chicago for a bachelor party, business ’do or two-day layover, Flight Club Darts at Wacker and Clark is the perfect place to wind down after a day of sightseeing. Book yourself an “oche” (it rhymes with “hockey,” and refers to the lane between the dartboard and throwing line), then use the tablet to add players and select from a menu of games (“Killer” is the only one you need). Scoring is automatic, drinks service dangerously attentive, and a memorable night out is guaranteed.

Chicago travel tip: Reserve your oche using Flight Club’s online booking system as early as possible. After work and on weekends, they’re in high demand.

On a tight budget? These are the cheapest times to visit the world’s top tourist destinations.

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Things to do in Chicago: Urban Kayaks
Photo: Joshua Mellin

Paddle the Chicago River

There’s no better way to soak up the city’s majestic architecture than by cruising down the Chicago River. Although the big cruise boats certainly have their perks (particularly if you’ve already spent the day pounding the pavement), the more adventurous option is to grab a paddle and take to the water with Urban Kayaks’ Historic Chicago Tour. After launching your kayak from the south bank of the river between Columbus and Lake Shore, you’ll follow your guide on a 90-minute loop to historic Wolf Point, passing such legendary structures as the Wrigley Building, the Jewelers Building and Merchandise Mart. Even if you’ve cruised the river before, being directly on the water’s surface provides a refreshing new perspective on these architectural gems, and the guide’s commentary—delivered via bullhorn—is much more colourful than the pre-recorded commentary you’ll get on a cruise boat. (You certainly won’t hear the jaw-dropping tale of the Dave Matthews Band’s Kinzie Bridge disaster told elsewhere…)

Chicago travel tip: Don’t forget to look up as you paddle under the bridges. It’s strangely thrilling to see the undercarriages of passing vehicles through the steel grating directly overhead.

Consider yourself an adrenaline junkie? Check out the world’s most extreme travel adventures.

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Things to do in Chicago: Art Institute of Chicago
Photo: Art Institute Of Chicago/WikiCommons

Make a Date With a Masterpiece

As you’d expect from the second largest art museum in the U.S., the Art Institute of Chicago houses a vast repository of important and instantly recognizable American works. From Edward Hopper’s Nighthawks to Georgia O’Keeffe’s sprawling Sky Above Clouds IV, it’s essentially a greatest hits collection from the country’s most influential artists, assembled in one labyrinthine gallery. What’s perhaps more surprising, however, is the depth of the institute’s European collection, which includes a bewildering number of pieces you might assume would be hanging in the great galleries of Paris and Amsterdam. Here, you’ll find such master works as Seurat’s A Sunday on La Grande Jatte and six of Monet’s series of 25 Stacks of Wheat. Among the most visually arresting, however, is Caillebotte’s Paris Street, Rainy Day (above), with its breathtaking near-photographic realism.

Chicago travel tip: Go early. Like most museums in Chicago, the Art Institute closes at 5PM daily (the exception is Thursdays, when it’s open until 8PM).

In the mood for more French masters? Don’t miss our ultimate travel guide to Paris.

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Things to do in Chicago: The Bean in Millennium Park
Photo: Shutterstock

Be Seen With the Bean

Just next door to the Art Institute is Millennium Park, where you can check off another requisite of any trip to the Windy City: a selfie with “the Bean.” Although it’s been Instagrammed so often it’s borderline cliché, there’s no denying the sculpture’s seamless mirrored finish provides a bucket-list worthy photo opp—and one of the biggest draws for the park’s 25-million visitors annually. If you Boomerang, nothing beats the Crowd Fountain: a pair of 50-foot LED towers projecting images of faces that “spit” streams of water. (It’s more tasteful than it sounds.) After you’ve snagged the perfect action shot, lose your shoes and soothe your tired tootsies in the reflecting pool—the fountain is open for wading between May and October.

Chicago travel tip: Feeling peckish at the park? Hop across the street to The Gage, which serves up one of Michigan Avenue’s best brunches. If you only order one item on the menu, make it the salted caramel and cinnamon sugar sticky bun. Seriously drool-worthy.

Here are more tourist traps that are actually worth visiting.

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Things to do in Chicago: Field Museum mummies
Photo: Brett Walther

Travel Through Time at the Field Museum

It’s not often you find a tourist attraction that genuinely appeals to all ages, but Chicago’s 125-year-old Field Museum pulls it off with aplomb. Kid-friendly without ever being condescending, the exhibits cover all the ground you could hope for in a natural history museum—namely dinosaurs, meteorites and mummies. The latter is perhaps the most impressive here, with the linen-wrapped remains of Ancient Egypt’s most wealthy presented alongside MRI scans of what lies beneath the bandages, and the occasional 3D rendering of what the occupant would have looked like in life. Magpies will gravitate to the third floor’s Grainger Hall of Gems, which includes the Chalmers Topaz—a dazzling 5,899 carats of powder blue brilliance.

Chicago travel tip: If you’re considering catching the Art Institute of Chicago, the Field Museum and the nearby Shedd Aquarium on your visit, it’s worth investing in a Chicago CityPASS. Not only does it cost less than admission to these three attractions, but it also includes VIP access to a number of other popular sites, including Skydeck Chicago and the Museum of Science and Industry.

Here are 10 more must-visit museums from around the world.

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Things to do in Chicago: John Hancock skyline
Photo: Choose Chicago

Sip a Cocktail in the Clouds

You can’t visit the birthplace of the skyscraper without scaling one of its iconic towers. Chicago boasts several vertigo-inducing observation decks, but you can skip the ticket fees (and the notoriously long lineups) if you spring for pre-dinner drinks at the top of the John Hancock Centre. Perched 1,000 feet above the Magnificent Mile, the Signature Lounge at the 96th combines an impressive cocktail menu with a breathtaking birds-eye view of Chicago and beyond (on a clear day, you can see as many as four states). Although bubbles are pricey and service patchy at best, the elevator ride is free and the vista—particularly at sunset—unforgettable.

Chicago travel tip: Ladies, you’re in luck. One of the best views at the Signature Lounge is actually from the ladies restroom.

Got nerves of steel? Here are more observation decks with terrifying views!

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Things to do in Chicago: Garrett popcorn
Photo: Garrett

Grab a Tin of Garrett’s

If you come back from Chicago without a tin of Garrett popcorn, were you even really there? Prized as both a snack and souvenir, Garrett popcorn is second only to deep-dish pizza as the definitive Windy City delicacy. Apart from its 69-year history, exactly what makes this purveyor of popcorn so legendary? Two words: “Garrett Mix.” Half caramel corn, half cheese corn, it’s a blend of sweet and salty that’s sure to get you salivating. The best part? With 12 locations across the city, including two in O’Hare airport (be sure to leave room in your carry-on), they’re nearly as plentiful here as Starbucks.

Don’t miss our next 48-hour city guide: 10 Things To Do in Delhi on a Two-Day Layover!

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