Sugar crawl hits family-friendly sweet spots in downtown Chicago

It’s possible that “Sugar, sugar” could be my family’s theme song. We all have a powerful sweet tooth. While we try hard to be healthy the majority of the time, we occasionally indulge in some fun sugary snacks or desserts at our favorite sweet spots in downtown Chicago and River North.

Magnolia Bakery


We’ve enjoyed visiting each spot individually, but one of my Chicago goals is to do a go a little crazy and do a “sugar crawl” by visiting each spot. It may be how we celebrate the next family birthday. On second thought, maybe it’s best that we stick with the “all things in moderation” approach. Either way, sitting down to share something yummy with my daughter can be a great way to connect with her, and that’s the sweetest treat of all.

Ghiradelli Chocolate Cafe

400 N. Michigan (The Wrigley Building)

Must try: Go for the World Famous Hot Fudge Sundae because handmade hot fudge from this 163-year-old chocolate company really is amazing.

There’s something special about a sundae and two (or more) spoons in an ice cream parlor, and it can be a great way to connect. Don’t rule Ghiradelli out if it’s too cool for ice cream. The hot chocolate is decadent and the Sea Salt Caramel Hot Cocoa is yummy enough to make you want to welcome winter with open arms.

Molly’s Cupcakes

419 N. Illinois (You can also visit the original location at 2536 N. Clark St.)

Must try: The flourless chocolate cake cupcake, dulce de leche ganache filling, french vanilla buttercream and chocolate drizzle will satisfy even the fiercest chocolate craving. If you’re feeling fruity, go with the raspberry and cream cupcake, which is vanilla cake with raspberries baked in, white chocolate mousse and raspberry buttercream.

Cupcakes and swings in one store? So fun! The owner named the store after his third grade teacher who would bring in cupcakes for her students, and that joy of childhood is evident inside. You can get classic cupcakes, vegan cupcakes or their famous filled cupcakes, which change seasonally. I also love that you can get a mini-Molly size for just $1.45 if you’re looking for something a little smaller.

Dylan’s Candy Bar

445 N. Michigan Ave.

Must try: The non-alcoholic drinks based on candy are really fun, and the Blue Poppin’ Shark Tank is a show stopper featuring cotton candy, simple syrup, lemon and Nerds with a gummy shark, Swedish Fish, Pop Rocks and a rock candy swizzle stick. If you prefer food, it’s fun to order the “Me Want Cookies om nom nom” just because that’s fun to say, but the freshly-baked cookie served warm with ice cream will warm your body and soul.

As a candy store, Dylan’s is in a league by itself and calling it a sugar lover’s paradise may be an understatement. What many miss out on, however, is the whimsical cafe on the premises. You can get savory items, but the standouts are, of course, the sweet treats. Get a seat at the window with your kids and enjoy the people watching on Michigan Ave. (You can read more about founder Dylan Lauren here.)

Magnolia Bakery

108 N. State St. (Block 37)

Must try: The whoopie pies are the perfect way to fully embrace the nostalgic feel of this bakery. You can opt for Red Velvet Whoopie Pies with whipped vanilla between two red velvet cakes or Devil’s Food which features caramel cream cheese icing between two devil’s food cakes.

Step back in time and soak up all the vintage charm and timeless tasty treats at Magnolia Bakery. While known for their cupcakes, they aren’t the only stars here. You can also find fun, old-fashioned favorites like banana pudding, icebox cakes, pies and whoopie pies. Look at it as giving your child a culinary history lesson while delighting your taste buds and nourishing your souls with some special time together.

- Advertisement -


40 Summer Festivals for Families in Chicagoland

Explore our iconic festival scene.

Watch This, Do That: The Parent Trap (1998)

'Sisters? Hallie, we're like twins!'

How to Pick the Best Sunscreen for Your Kids

Protect your family's skin this summer with these tips.

- Advertisement -