City Cast

Where to Shop Local in Chicago This Holiday Season

Sidney Madden
Sidney Madden
Posted on November 21   |   Updated on November 29
Merch at the Silver Room

Merch at the Silver Room. (Jacoby Cochran / City Cast Chicago)

City Cast

Eat, Shop, and Give in Our Neighborhoods


Small Business Saturday is around the corner, and we’re rounding up some local businesses for you to start your holiday shopping.

Chicago Knick Knacks

  • ❤️ Transit Tees in Wicker Park and Andersonville has Chicago games inspired by the 1893 World Fair, the Chicago Handshake, and more.
  • 💙 The Silver Room in Hyde Park has all types of gifts from South Side–themed candles to Chicago apparel to books by local authors.


  • 🌱 ​​The Catalina Plant Co. in Jefferson Park is a destination for plant lovers between its changing inventory and classes.
  • 💐 Southside Blooms delivers flowers locally — including bouquet-of-the-week subscriptions.

Self Care

  • 🧼 Scratch Goods in West Loop sells scrubs, oils, brushes, and towels. Pay for your loved one’s self-care club membership or a mask bar time slot.
  • 💆 A Natural Mind & Body in Austin offers massages for everyone from athletes to pregnant people.
Hey Chicago newsletter editor outside The Last Chapter Book Shop earlier this fall

Your fav newsletter editor waited in a long line for the grand opening of The Last Chapter Book Shop earlier this fall. (Sidney Madden / City Cast Chicago)


  • 📕 The Last Chapter Book Shop in Roscoe Village has novels for the hopeless romantic in your life.
  • 📗 Semicolon Bookstore & Gallery in River West is the city’s largest Black woman–owned bookstore with a wide selection of stacks, regular events, and kids section.
  • 📘 Bookie’s in Beverly lets you trade in books for credit, which means you can get gifts for your bookworms while on a budget.


  • 👕 Englewood Branded has T-shirts, snapbacks, and hoodies.
  • 👗 Lost Girls Vintage in West Town and Logan Square has a big sale online and in store this week off all things vintage.
  • 🛍️ Knee Deep Vintage in Pilsen has lots of unique pieces — including ones from Japan after a recent trip.
  • 👟 Big ‘N Little Shoes in Mount Greenwood sells footwear of all sizes for all occasions.
Hey Chicago

Want to know what's happening in Chicago? Sign up for our free newsletter, Hey Chicago. Packed with local news, curated event recs, local life hacks, and more, it's your daily toolkit for getting the most out of the city you love.

Chicago's Best

See All