For this post in the (Re)discover Chicagoland Neighborhood Series, ULI Chicago went off the beaten path and explored Chicagoland alleyways! Check out our alley-finds below and don’t forget to share your own favorite unusual places with #rediscoverchicagoland.

Alleys are an integral part of Chicago’s urban structure – they are the reason why our streets are lined with friendly porches instead of blank garage doors, and why we don’t have to dodge large garbage bins every time we stroll down the sidewalk! While alleys clearly play a critical service role and help create walkable, inviting streets, they are rarely destinations themselves. Creative entrepreneurs are changing that by turning unusual spaces in alleys into delightful, unique destinations.

Pickwick Stable
Tucked at the end of Pickwick Place, a narrow alley off Jackson Boulevard, sits one of the oldest and smallest buildings in Chicago’s Loop – Pickwick Stable. Now home to a coffee shop and dressed with outdoor seating, it’s the perfect place to stop on your way to enjoy the Wabash Corridor’s Big Walls!

Bookends and Beginnings
A short detour down the alley off Sherman Avenue in downtown Evanston will lead you to Bookends and Beginnings – a thoughtfully curated, independent bookstore ideal for finding bestsellers as well as rare books.

Do you know of other interesting alleyways?  With more than 1,900 miles of them within Chicago’s borders, there’s bound to be more. We’d like to know!

FUN FACT: The Chicago Loop Alliance’s ACTIVATE program temporarily transforms a downtown alley into a pop-up display of art and music for an evening to create a unique urban experience. Attend the next Activate event, scheduled for September 15, to see how artists are reimagining alleys.