CHICAGO
There’s a multitude of reasons to visit the Windy City, from the mouthwatering food scene and dynamic neighbourhoods to that warm Midwestern welcome. It’s also the start of the iconic Route 66.
Take a boat ride on Lake Michigan, soaking up the city’s bold architecture, before strolling down the Magnificent Mile, home of luxe fashion outlets and fine-dining restaurants.
We loved exploring Millennium Park. Spread over 24 acres, it’s one of the largest green roof parks in the world. Built over parking garages and a rail yard, it’s now buzzing with outdoor music venues, public art, food concessions, theatre and children’s play zones. We also had to grab a mirror-selfie in the reflection of the Bean, a huge quirky sculpture in the city.
Sports fans should head to Wrigley Field for a Chicago Cubs baseball game or visit the United Center atrium to pose by the statue of basketball star Michael Jordan before a Chicago Bulls game.
Our weekend highlight was a food tour with the award-winning Bobby’s Bike Hike. Our guide Nate showed us a combo of Instagram-worthy landscapes and heavenly local delicacies. Our favourite spots were Lou Malnati’s, for the best deep-dish pizza, The Wiener’s Circle, where we stopped for a ketchup-free Chicago hotdog, and Oprah Winfrey’s favourite bakery Bittersweet, for the most delectable chocolate brownie.
Don’t miss Navy Pier’s Centennial Wheel and the incredible views from the 360 Chicago observation deck, and take in the inspiring Van Gogh exhibition at the Art Institute of Chicago.
JOLIET AND PONTIAC
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