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How to Spend 48 Hours in Chicago
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How to Spend 48 Hours in Chicago

Picture of Tim Marklew
Updated: 14 April 2017
Two days aren’t nearly enough time to discover all that the Windy City has to offer, but you can give it a good go. So strap yourself in; it’s going to be a BIG 48 hours.

Day One

Morning

There’s only one way to start 48 hours in Chicago, and that’s by eating. Grab a croissant sandwich or some cranberry and orange pancakes at the Bongo Room in the South Loop, conveniently located next to Museum Campus. There you’ll find the Shedd Aquarium, the Adler Planetarium, and the Field Museum, home to the world’s largest T-Rex, so choose your favorite.

Shedd Aquarium and Adler Planetarium at Museum Campus | © Heather Paul/Flickr
Shedd Aquarium and Adler Planetarium at Museum Campus | © Heather Paul/Flickr

Afternoon

Wander up Michigan Avenue to Cloud Gate to get your picture taken with the “Bean,” before continuing up to the Magnificent Mile, where you can work up an appetite with some serious shopping. Enjoy some deep-dish pizza at Giordano’s or Gino’s East. Be careful how much you order because, while leftovers are all well and good, they’re heavy to carry around all day.

Walk off your food by heading over to Navy Pier and ride the Ferris wheel for an amazing panorama. Head back to the Mile and continue north to the John Hancock Tower where, if you’re sensible, you can grab a drink in the Signature Room on the 95th floor, or, if you’re not, you can try Tilt, where you stand in a box and are tilted out for a better look at the ground 1,000 feet below.

Cloud Gate in Millennium Park | © jmcmichael/Flickr
Cloud Gate in Millennium Park | © jmcmichael/Flickr

Evening

With your feet back on the ground, it’s time to head north for some Chicago Blues. Kingston Mines in Lincoln Park has two stages that alternate seven nights a week, so there’s never a quiet moment. If you’re hungry again by the time you leave, head to the nearby Wieners Circle for a late-night Chicago-style hot dog with a side of abuse from its famously surly staff.

Day Two

Morning

Kickstart your second day with fresh-roasted coffee from Intelligentsia’s Millennium Park coffeebar, and try some gourmet popcorn from Garrett. Flavors include Buttery Ranch and Cashew Caramel Crisp, but actually the Chicago favorite is a mix of the sweet Caramel Crisp and savory Cheese Corn. With your snack in hand, it’s time to take to the water with a boat tour from the Chicago Architecture Foundation, where you can learn all you need to know about some of the world’s oldest and tallest skyscrapers.

Chicago Architecture Foundation river cruise | © Bill Ward/Flickr
Chicago Architecture Foundation river cruise | © Bill Ward/Flickr

Afternoon

For lunch head to River North for another Chicago speciality from Mr. Beef on N. Orleans Street. The Italian beef sandwich is piled high with thin slices of slow-cooked beef, dripping with its own juices and pickled vegetables. Remember it’s cash only, and eat it there to avoid making too much of a mess.

Once you’re full again, head northwest to Bucktown and pick up the 606, a repurposed elevated train line that’s now an urban trail offering a peaceful walk between some of the city’s best neighborhoods and vistas. Depart when you cross Milwaukee Avenue and head down into Wicker Park where you can while away the time in interesting galleries, bookshops, and boutiques.

The 606 | © Colin Hinkle/courtesy of The Trust for Public Land
The 606 | © Colin Hinkle / Courtesy of The Trust for Public Land

Evening

If it’s the right time of year and the Cubs are in town, there’s no better way to spend an evening in Chicago than by taking in a ballgame. Soak up the history of Wrigley Field’s ivy-covered walls and hand-turned scoreboard, or get rowdy with a beer on the bleachers—it’s all good. If baseball’s not in season, head to Second City in Old Town for some improv comedy. This is where many popular comedians got their big break.

Wrigley Field | © Jeremiah Wong/Flickr
Wrigley Field | © Jeremiah Wong/Flickr