Best Hot Chocolate and Cookies in Chicago — A Sweet Guide to Holiday Treats for Santa!

Posted by Jeffrey Pernito

Chicago winters call for rich hot chocolate and delicious cookies, and whether you’re exploring downtown or chilling in cozy neighborhoods, the city is packed with sweet spots perfect for sharing with friends and family — and definitely for leaving out at Christmas! Here’s our curated list of must‑visit places featuring stellar hot chocolate drinks and top cookie destinations.

Best Places for Hot Chocolate in Chicago

When Chicago gets chilly, nothing beats a rich, decadent hot chocolate. From classic cocoa to over-the-top creations, these are the best spots for hot chocolate in the city.

  • Cocoa + Co.

    This local favorite is known for decadent, ultra‑chocolatey hot drinks with creative options like spice‑infused or super‑rich dark hot chocolate — perfect for warming up after a winter walk. Their cocoa is regularly touted as some of the city’s best.

  • JoJo's Shake Bar

    While famous for shakes, JoJo’s also serves great hot chocolate, especially during seasonal events with topping bars and festive experiences — ideal for photos with Santa or a sweet family outing.

  • Chiqueolatte Chicago

    A beloved neighborhood café with excellent hot drinks, including classic and specialty hot chocolate. Great for a relaxing break during a winter day of shopping or holiday activities.

  • Bombobar

    BomboBar’s walk-up window is a must-visit for over-the-top Hotter Chocolates. Try the s’mores flavor with chocolate, graham crackers, and toasted marshmallows, or the Cookie Crumble topped with Oreos, cookie bits, and dough. You can even spike it with spirits! Find them in the West Loop outside Bar Siena.

  • Katherine Anne Confections

    Named one of the best places for hot chocolate in America, this shop’s luxurious drinking chocolate is a must-try. Made from pure ground chocolate melted with milk and cream, flavors this year include super dark, semisweet, salted caramel, and Mexican hot chocolate. Grab a few to take home — perfect for stocking stuffers!

Best Cookies & Sweet Shops in Chicago

Chicago’s cookie scene is seriously sweet. From local bakeries to beloved national spots, here are favorites locals and visitors rave about:

  • Chip City

    This popular cookie shop is known for giant, chewy cookies with flavors like Brown Butter, Cookie Butter, and more — a perfect Santa treat. Locals rate these among the best chocolate chip cookies in the city.

  • Levain Bakery

    From New York to Chicago, Levain’s thick, gooey‑center cookies are legendary and make for an indulgent treat alongside hot chocolate.

  • Sugar Moon Bakery

    This bakery is beloved for its fresh, handcrafted cookies and pastries — a cozy, neighborhood favorite for holiday snack runs.

  • Sweet Mandy B's

    A longtime Chicago favorite, Sweet Mandy B’s serves classic, nostalgic cookies and sweets — ideal for Christmas cookie plates.

  • Big Fat Cookie

    Living up to its name, this spot serves large cookies with loads of flavor — perfect for sharing (or not!).

Final Thoughts

Chicago is full of cozy spots serving rich hot chocolate and delicious cookies — perfect for holiday treats, family outings, or creating memorable experiences in the city. From festive neighborhoods to local favorites, there’s something sweet for everyone this season.

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