Whether you’re visiting Chicago, entertaining a guest, or rediscovering your own backyard, these seven miles will lead you through the city’s best. This walk is suited for day or night, though we recommend picking a warm day–this is the Windy City, after all.
Start at the Adler Planetarium at the edge of Museum Campus. It’s one of the most incredible views of the city you’ll find. Walk down the path towards South Columbus Drive, and when you reach it, keep heading north through Grant Park. When you reach Jackson, take a left, but don’t cross the street. Instead, hang a right and stay on that side. You’ll walk past the Art Institute with its iconic lion statues. Make a stop there if you want, but just be warned you could easily walk an extra seven miles just wandering around inside.
Walk a bit farther north until you reach Monroe, cross the street, and take a right. When you hit South Columbus Drive, take a left through the magnificent Lurie Gardens, and keep on walking west until you hit North Michigan again. You’ll head straight through Millennium Park, where you’ll of course see The Bean. Walk a little north, pass the Cultural Center (which hosts tons of free events), and take a left on Randolph Street. Keep walking until you get to State Street that great street, and take a right. Before you do, take a gander over at the majestic Oriental Theatre.
Next stop, another theatre–this time, the iconic Chicago Theatre. After you’ve taken it all in, keep walking until you hit Lake Street, and take a left. At the corner of Clark and Lake, you’ll see one of the most incredible feats of architecture in the city: the Thompson Center. It’s like a modern day pyramid. We definitely recommend stopping in to see if from the inside.
At Upper Wacker, take a right until you hit Dearborn, and then head down the stairs to the Chicago River Walk. Enjoy the massive buildings overhead and the calm current of the large river that cuts the city in half. Once you get to Michigan Avenue, come back up to street level and cross the bridge north.
Once you get to Grand, just after Michael Jordan’s Steak House, walk down the stairs and start heading east towards the lake. You should be seeing the Ferris wheel, and you guessed it, it’s time for some Navy Pier action. Walk from one end to the other, check out the tourist traps, ride the Ferris wheel, and have some good old-fashioned fun!